Language：Japanese   Publisher：日本分子イメージング学会  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Science  

In this study, we successfully synthesized a small-sized gold nanocluster (2 nm) coated with homogeneous tripeptides bearing azido and amino groups that enable facile multifunctionalizations. Using sodium phenoxide to reduce tetrachloroauric(iii) acid in the presence of the cysteine-containing tripeptide, we efficiently prepared the gold nanoclusters without damaging the azido group. We then utilized this clickable bisreactive nanocluster as a versatile platform for synthesizing multifunctionalized gold nanomaterials. The resulting nanoclusters were conjugated with an anticancer compound connected to an indolizine moiety for photoinduced uncaging, a photodynamic therapy agent acting as a photosensitizer for uncaging, and a cyclic RGD peptide. The cytotoxicity of the multifunctionalized gold nanoclusters was demonstrated through red light irradiation of human lung cancer-derived A549 cells treated with the synthesized nanomaterials. The significant cytotoxicity exhibited by the cells underscores the potential utility of this method in advanced cancer therapies.

DOI： 10.1039/D3SC04365G

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Other Link： https://pubs.rsc.org/en/content/articlelanding/2024/sc/d3sc04365g

Repository Public URL： https://hdl.handle.net/2324/7174362

Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

An efficient method for generating 3-triazenylarynes from ortho-iodoaryl triflate-type precursors was developed. The generated arynes reacted with various arynophiles with high regioselectivity because of the triazenyl group. The 3-triazenylaryne precursors functioned as useful intermediates of diverse multisubstituted aromatic compounds through the transformation of the remaining triazenyl group of aryne adducts and triazenyl group-directed ortho-C-H functionalization.

DOI： 10.1021/acs.orglett.3c02615

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

BACKGROUND: Of interest to women's mental health, a wealth of studies suggests sex differences in nicotine addiction and treatment response, but their psychoneuroendocrine underpinnings remain largely unknown. A pathway involving sex steroids could indeed be involved in the behavioural effects of nicotine, as it was found to inhibit aromatase in vitro and in vivo in rodents and non-human primates, respectively. Aromatase regulates the synthesis of oestrogens and, of relevance to addiction, is highly expressed in the limbic brain. METHODS: The present study sought to investigate in vivo aromatase availability in relation to exposure to nicotine in healthy women. Structural magnetic resonance imaging and two [11C]cetrozole positron emission tomography (PET) scans were performed to assess the availability of aromatase before and after administration of nicotine. Gonadal hormones and cotinine levels were measured. Given the region-specific expression of aromatase, a ROI-based approach was employed to assess changes in [11C]cetrozole non-displaceable binding potential. RESULTS: The highest availability of aromatase was found in the right and left thalamus. Upon nicotine exposure, [11C]cetrozole binding in the thalamus was acutely decreased bilaterally (Cohen's d = -0.99). In line, cotinine levels were negatively associated with aromatase availability in the thalamus, although as non-significant trend. CONCLUSIONS: These findings indicate acute blocking of aromatase availability by nicotine in the thalamic area. This suggests a new putative mechanism mediating the effects of nicotine on human behaviour, particularly relevant to sex differences in nicotine addiction.

DOI： 10.1016/j.comppsych.2023.152381

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media {LLC}  

<jats:title>Abstract</jats:title><jats:p>The development of a conjugation method initiated by irradiation of long-wavelength light (&gt;500 nm) to prepare densely functionalized molecules while avoiding undesired photodegradation has attracted considerable attention. Here we show an amide bond formation method based on the photoreaction of 3-acylindolizines in the presence of amines triggered via red-light irradiation. Photooxidation of 3-acylindolizines using a catalytic amount of a photosensitizer and red light-emitting diodes (660 nm) affords the corresponding conjugated amides in nearly quantitative yields within &lt;5 min. This transformation can be performed in aqueous organic solvents and is applicable to diverse aliphatic amines with various functional groups, including the moieties responsive to short-wavelength light.</jats:p>

DOI： 10.1038/s42004-022-00712-5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Protein Expression and Purification  

The kinase DYRK1A phosphorylates substrate proteins that are involved in the progression of many diseases. DYRK1A also phosphorylates its own residues on key elements intramolecularly to activate and stabilize itself during the folding process. Once the folding process of DYRK1A has completed, it can no longer catalyzes the intramolecular reaction, suggesting that a transitional intermediate state that catalyzes the autophosphorylation exists. In the previous study, we identified a small molecule, designated as FINDY, that selectively inhibits the folding intermediate of DYRK1A. Although evidence has suggested that FINDY targets the ATP-binding pocket of DYRK1A, it remains elusive as to whether the DYRK1A kinase domain could be purified as a complex with FINDY. In this study, we successfully expressed and purified the kinase domain of DYRK1A in complex with FINDY. The DYRK1A kinase domain was expressed as a fusion protein with a hexahistidine tag and ZZ-domain (His-ZZ-DYRK1A) at 6 °C by using a cold shock induction system in Escherichia coli cells. The cells were incubated with FINDY. The cell pellets were gently extracted on ice and subjected to immobilized-metal affinity chromatography. The amount of FINDY in the elution fraction was measured by UV absorbance specific for FINDY. The eluate contained FINDY with the ratio of FINDY to DYRK1A protein being 0.15 in quadruplicate experiments. Thus, this study demonstrates the direct interaction between the DYRK1A kinase domain and FINDY, paving the way for structural determination of the complex.

DOI： 10.1016/j.pep.2022.106089

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Physical Society of Japan  

To understand the chemical origin of life, we studied the probability of amino acid production via β-decay from radiocarbon (14C)-containing carboxylic acid. We developed a numerical simulation code that uses a Monte Carlo method for calculating the initial condition (recoil momentum of 14N in 14C β-decay) and subsequent dynamical trajectory. We evaluated the productivity of the simplest amino acid [glycine (glycinium)] via 14C β-decay in [3- 14C]propionic acid as the probability of daughter nuclide 14N remaining in the compound using the developed simulation. As a result, the probability of glycinium production was determined to be approximately 81%, assuming the molecular structures of [3-14C]propionic acid and glycinium with amino group bonding dissociation energy of 3.9 eV estimated using the density-functional theory (DFT) method. Furthermore, according to the calculations with various bonding dissociation potential parameters, a probability of glycinium production of approximately 32% was expected even with a loose amino group bonding dissociation energy of 2 eV.

DOI： 10.7566/jpsj.91.064301

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Language：English   Publisher：(一社)日本薬物動態学会  

肝胆道系輸送の定量評価のためのPETプローブとして[18F]ピタバスタチン([18F]PTV)を開発し、健常者を対象に臨床PET試験を行った。リファンピシン前投与あり/なしの条件下でPETプローブの薬物動態特性を調べた。リファンピシン前投与は肝臓におけるプローブの最高濃度および胆汁排泄を対照のそれぞれ52%および34%に低下させた。リファンピシン前投与は肝取り込みクリアランスを顕著に低下させ、胆汁排泄クリアランスを軽度低下させた。以上より、[18F]PTVは肝胆道系の取り込み/排出トランスポーターの活性を臨床的に調べるためのプローブとして有用と考えられた。

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry ({RSC})  

<jats:p>Iridium-catalyzed azide–thioalkyne cycloaddition was found to be effective for the azido-type-selective reaction of various multiazido compounds, enabling facile synthesis of multitriazole compounds in short steps.</jats:p>

DOI： 10.1039/d2cc01739c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

It is widely accepted that uptake and efflux transporters on clearance organs play crucial roles in drug disposition. Although in vitro transporter assay system can identify the intrinsic properties of the target transporters, it is not so easy to precisely predict in vivo pharmacokinetic parameters from in vitro data. Positron emission tomography (PET) imaging is a useful tool to directly assess the activity of drug transporters in humans. We recently developed a practical synthetic method for fluorine-18-labeled pitavastatin ([18F]PTV) as a PET probe for quantitative evaluation of hepatobiliary transport. In the present study, we conducted clinical PET imaging with [18F]PTV and compared the pharmacokinetic properties of the probe for healthy subjects with or without rifampicin pretreatment. Rifampicin pretreatment significantly suppressed the hepatic maximum concentration and biliary excretion of the probe to 52% and 34% of the control values, respectively. Rifampicin treatment markedly decreased hepatic uptake clearance (21% of the control), and moderately canalicular efflux clearance with regard to hepatic concentration (52% of the control). These results demonstrate that [18F]PTV is a useful probe for clinical investigation of the activities of hepatobiliary uptake/efflux transporters in humans.

DOI： 10.1016/j.dmpk.2022.100449

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：European Journal of Medicinal Chemistry  

DYRK1A phosphorylates proteins involved in neurological disorders in an intermolecular manner. Meanwhile, during the protein folding process of DYRK1A, a transitional folding intermediate catalyzes the intramolecular autophosphorylation required for the "one-off" inceptive activation and stabilization. In our previous study, a small molecule termed FINDY (1) was identified, which inhibits the folding intermediate-catalyzed intramolecular autophosphorylation of DYRK1A but not the folded state-catalyzed intermolecular phosphorylation. However, the structural features of FINDY (1) responsible for this intermediate-selective inhibition remain elusive. In this study, structural derivatives of FINDY (1) were designed and synthesized according to its predicted binding mode in the ATP pocket of DYRK1A. Quantitative structure-activity relationship (QSAR) of the derivatives revealed that the selectivity against the folding intermediate is determined by steric hindrance between the bulky hydrophobic moiety of the derivatives and the entrance to the pocket. In addition, a potent derivative 3 was identified, which inhibited the folding intermediate more strongly than FINDY (1); it was designated as dp-FINDY. Although dp-FINDY (3) did not inhibit the folded state, as well as FINDY (1), it inhibited the intramolecular autophosphorylation of DYRK1A in an in vitro cell-free protein synthesis assay. Furthermore, dp-FINDY (3) destabilized endogenous DYRK1A in HEK293 cells. This study provides structural insights into the folding intermediate-selective inhibition of DYRK1A and expands the chemical options for the design of a kinase inhibitor.

DOI： 10.1016/j.ejmech.2021.113948

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.joc.1c01244

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Others   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.joc.0c02474

Language：English   Publishing type：Research paper (scientific journal)  

Aromatase, the enzyme that in the brain converts testosterone and androstenedione to estradiol and estrone, respectively, is a putative key factor in psychoneuroendocrinology. In vivo assessment of aromatase was performed to evaluate tracer kinetic models and optimal scan duration, for quantitative analysis of the aromatase positron emission tomography (PET) ligand [11 C]cetrozole. Anatomical magnetic resonance and 90-min dynamic [11 C]cetrozole PET-CT scans were performed on healthy women. Volume of interest (VOI)-based analyses with a plasma-input function were performed using the single-tissue and two-tissue (2TCM) reversible compartment models and plasma-input Logan analysis. Additionally, the simplified reference tissue model (SRTM), Logan reference tissue model (LRTM), and standardized uptake volume ratio model, with cerebellum as reference region, were evaluated. Parametric images were generated and regionally averaged voxel values were compared with VOI-based analyses of the reference tissue models. The optimal reference model was used for evaluation of a decreased scan duration. Differences between the plasma-input- and reference tissue-based methods and comparisons between scan durations were assessed by linear regression. The [11 C]cetrozole time-activity curves were best described by the 2TCM. SRTM nondisplaceable binding potential (BPND ), with cerebellum as reference region, can be used to estimate [11 C]cetrozole binding and generated robust and quantitatively accurate results for a reduced scan duration of 60 min. Receptor parametric mapping, a basis function implementation of SRTM, as well as LRTM, produced quantitatively accurate parametric images, showing BPND at the voxel level. As PET tracer, [11 C]cetrozole can be employed for relatively short brain scans to measure aromatase binding using a reference tissue-based approach.

DOI： 10.1002/jnr.24707

Language：English   Publishing type：Research paper (scientific journal)  

The irradiation of red light-emitting-diode light (λ = 660 nm) to 3-acyl-2-methoxyindolizines in the presence of a catalytic amount of methylene blue triggered the photooxidation of the indolizine ring, resulting in a nearly quantitative release of alcohols or carboxylic acids within a few minutes. The method was applicable for photouncaging various functional molecules such as a carboxylic anticancer drug and a phenolic fluorescent dye from the corresponding indolizine conjugates, including an insulin-indolizine-dye conjugate.

DOI： 10.1021/acs.orglett.0c01799

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.molpharmaceut.9b01284

Language：English   Publishing type：Research paper (scientific journal)  

Synthesis of (2,2-Diborylvinyl)arenes by Rhodium-Catalyzed Desulfanylative gem-Diborylation of 2‑Arylvinyl Sulfides

Language：English   Publishing type：Research paper (scientific journal)  

Divergent synthesis of photoaffinity probe candidates by click reactions of azido-substituted aryltrifluoromethyldiazirines
Accepted (2018/10/5)

Language：English   Publishing type：Research paper (scientific journal)  

Palladium(II)-mediated rapid 11C-cyanation of (hetero)arylborons
A palladium(ii)-mediated rapid C-11-cyanation of (hetero)arylborons with [C-11]NH4CN/NH3 has been developed using bench-stable and readily available reagents. The method showed excellent functional-group tolerance, and allowed the highly efficient synthesis of a wide range of [C-11]cyanoarenes, including PET tracers for aromatase imaging. A mechanistic study of the C-11-cyanation suggests the instantaneous formation of a mono[C-11]cyanopalladium(ii) complex that reacts smoothly with arylborons.

DOI： 10.1039/C8OB02049C

Language：English   Publishing type：Research paper (scientific journal)  

Oxytocin (OXT) and arginine vasopressin (AVP) are structurally similar neuropeptide hormones that function as neurotransmitters in the brain, and have opposite key roles in social behaviors. These peptides bind to their G protein-coupled receptors (OXTR and AVPRs), inducing calcium ion-dependent signaling pathways and endocytosis of these receptors. Because selective agonists and antagonists for these receptors have been developed as therapeutic and diagnostic agents for diseases such as psychiatric disorders, facile methods are in demand for the evaluation of selectivity between these receptors. In this study, we developed a quantitative assay for OXT- and AVP-induced endocytosis of their receptors. The mutated Oplophorus luciferase, nanoKAZ, was fused to OXTR and AVPRs to enable rapid quantification of agonist-induced endocytosis by bioluminescence reduction. Agonist stimulation significantly decreases bioluminescence of nanoKAZ-fused receptors in living cells. Using this system, we evaluated clinically used OXTR antagonist atosiban and a reported pyrazinyltriazole derivative, hereby designated as PF13. Atosiban acted as an antagonist of AVPR1a, as well as an agonist for AVPR1b, whereas PF13 antagonized OXTR more selectively than atosiban, as reported previously. This paper shows a strategy for quantification of agonist-induced endocytosis of OXTR and AVPRs, and confirms its potent utility in the evaluation of agonists and antagonists.

DOI： 10.1016/j.ab.2018.04.001

Language：English   Publishing type：Research paper (scientific journal)  

Monodefluoroborylation of polyfluoroalkenes has been achieved in a regioselective manner under mild conditions via copper catalysis. The method has shown an extremely broad scope of substrates, including (difluorovinyl)arenes, tetrafluoroethylene (TFE), (trifluorovinyparenes, and trifluoromethylated monofluoroalkenes. The choice of boron source was important for the efficient transformation of (difluorovinyparenes; (Bpin)(2) was suitable for substrates with an electron-deficient aryl group and (Bnep)(2) for those with an electron-rich aryl group. Derivatization of the (fluoroalkenyl)-boronic acid esters to the corresponding potassium trifluoroborate salts has rendered the products easily isolable, which greatly improved the synthetic practicality of the mono defluoroborylation reaction. Stoichiometric experiments indicate that the fate of the regioselectivity depends on the mode of beta-fluorine elimination, which depends on the substrate. Further transformation of the boryl group has allowed facile preparation of fluoroalkene derivatives as exemplified by the synthesis of a fluoroalkene mimic of atorvastatin, which potently inhibited the enzyme activity of HMG-CoA reductase.

DOI： 10.1021/jacs.7b08343

Language：English   Publishing type：Research paper (scientific journal)  

A two-step transformation of alpha,beta-unsaturated carboxylic acids to alkenylboronic esters has been achieved via thioesterification of carboxylic acids followed by rhodium-catalyzed decarbonylative borylation of thioesters. The latter reaction proceeds under mild conditions with broad functional-group tolerance, rendering a wide range of alkenylboronic esters easily accessible.

DOI： 10.1246/cl.170549

Language：English   Publishing type：Research paper (scientific journal)  

ipso-Borylation of fluoroarenes has been achieved using an air-stable copper complex as a catalyst. Mechanistic studies suggest that the reaction proceeds via an S(RN)1 mechanism involving a single-electron-transfer (SET) process and not via the typical SNAr mechanism. This method differs from the previously reported nickel/copper-cocatalyzed system in terms of scope of the substrate and has exhibited good scalability. Double and triple ipso-borylations of several di- and trifluoroarenes have been also achieved efficiently, enhancing the synthetic utility of this method.

DOI： 10.1021/acscatal.7b01448

Language：English   Publishing type：Research paper (scientific journal)  

Transformation of aromatic thioesters into aryl-boronic esters was achieved efficiently using a rhodium catalyst. The broad functional-group tolerance and mild conditions of the method have allowed for the two-step decarboxylative borylation of a wide range of aromatic carboxylic acids, including commercially available drugs.

DOI： 10.1002/anie.201611974

Language：English   Publishing type：Research paper (scientific journal)  

A convenient method for the stereoinversion of secondary alcohols, applicable to stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethyl-formamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.

DOI： 10.1021/acs.orglett.6b02675

Language：English   Publishing type：Research paper (scientific journal)  

Rhodium-Catalyzed ipso-Borylation of Alkylthioarenes via C-S Bond Cleavage
Rhodium-catalyzed transformation of alkyl aryl sulfides into arylboronic acid pinacol esters via C-S bond cleavage is reported. In combination with transition-metal-catalyzed sitlfanyli group-guided regioselective C-H borylation reactions of alkylthioarenes, this method allows the synthesis of a diverse range of multisubstituted atenes.

DOI： 10.1021/acs.orglett.6b01250

Language：English   Publishing type：Research paper (scientific journal)  

Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes for Diverse C-F Bond Functionalizations
Ni/Cu-catalyzed transformation of fluroarenes to arylboronic acid pinacol esters via C-F bond cleavage has been achieved. Further versatile derivatization of an arylboronic ester has allowed for the facile two-step conversion of a fluoroarene to diverse functionalized arenes, demonstrating the synthetic utility of the method.

DOI： 10.1021/jacs.5b10119

Language：English   Publishing type：Research paper (scientific journal)  

The preparation of a new C-2-symmetrical chiral tridentate N-heterocyclic carbene (NHC) ligand coordinated Cr(III) complex is described. The new NHC ligand was prepared as its AgBr complex, which was stable but smoothly underwent carbene exchange reaction with CrCl2 to afford the new NHC ligand coordinated Cr(III) complex. The X-ray crystallographic analysis of the Cr(III) complex revealed its distorted octahedral form. The Cr(III) complex mediated reaction of allylbromide with benzaldehyde did not afford products under the catalytic conditions reported by us. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetasy.2015.01.003

Language：English   Publishing type：Research paper (scientific journal)  

Au(I)-catalyzed oxidative cyclizations that successfully convert 1,5-ene-ynes and a 1,6-ene-yne to the corresponding cycloalkanone-fused cyclopropanes are described. This Au(I)-catalyzed oxidative cyclization can be effectively applied to various substrates and is an alternative to the previously used intramolecular cyclopropanation that required potentially explosive diazo compound. (C) 2014 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2014.10.084

Language：English   Publishing type：Research paper (scientific journal)  

The preparation of imides via the palladium-catalyzed coupling reaction of organostannanes is described. The palladium-catalyzed coupling reaction of aryl-, heteroaryl-, and alkenyl(tributyl)stannanes with methyl N-[methoxy(methylthio)methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers, which are converted to the corresponding imides in high yield through acid hydrolysis.

DOI： 10.3987/COM-13-12662

Language：English   Publishing type：Research paper (scientific journal)  

Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides
Highly enantioselective catalytic asymmetric reactions of rationally designed α-alkylidene β-keto imides are described. The [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides proceed with high enantioselectivity and yield. The [4 + 2] cycloadditions of the imides with various dienes afford products bearing an all-carbon quaternary stereogenic center at the ring junction. α-Alkylidene β-keto imides should be useful for the enantioselective total synthesis of natural products and other catalytic asymmetric applications. © 2013 American Chemical Society.

DOI： 10.1021/ol303381c

Language：English   Publishing type：Research paper (scientific journal)  

The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio)methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.

DOI： 10.1021/ol303062a

Language：English   Publishing type：Research paper (scientific journal)  

In this report, we describe an iron(III) complex containing a carbazole-based tridentate ligand that catalyzes highly enantioselective asymmetric epoxidation of (E)-alkenes at room temperature. The non-heme iron(III) complex has a five-coordinated trigonal-bipyramidal structure, and its two-electron oxidized state has the similar electronic structure as that of iron porphyrins.

DOI： 10.1021/ja304219s

Language：English   Publishing type：Research paper (scientific journal)  

The palladium-catalyzed reductive cleavage of alkyl aryl sulfides to afford the corresponding arenes in high yield, which is both accelerated and exhibits increased functional group selectivity in the presence of TMSCI, is described. This ligand-free reaction features mild conditions, easy operation, use of readily available reagents, and high functional group selectivity. (c) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2012.06.002

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/asia.200900151

Language：English   Publishing type：Research paper (scientific journal)  

Carbon-carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine
Two N-benzyl imines are designed to allow for carbon-carbon bond formations at the aminated benzylic positions. Direct benzylic arylation reactions of N-benzylxanthone imine with aryl chlorides proceed under palladium catalysis in the presence of cesium hydroxide, yielding the corresponding benzhydrylamine derivatives. Alkylation reactions of N-benzyldi-1-naphthyl ketone imine with alkyl halides in the presence of potassium tert-butoxide afford the corresponding 1-phenylalkylamines in high yields. Conjugate addition of N-benzyldi-1-naphthyl ketone imine is also described. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2009.02.034

Language：English   Publishing type：Research paper (scientific journal)  

An effective palladium catalyst system for the direct arylation of benzyl sulfones with aryl halides has been developed. The catalytic reaction provides a facile route to diarylmethyl sulfones. The products can be transformed further via desulfonylative functionalization mediated by aluminum compounds. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2009.01.030

Language：English   Publishing type：Research paper (scientific journal)  

The direct benzylic arylation of IV-benzylxanthone imine with aryl chloride proceeds under palladium catalysis, yielding the corresponding coupling product. The product is readily transformed to benzhydrylamine. Taking into consideration that the imine is readily availablefrom benzylic amine, the overall transformation represents a formal cross-coupling reaction of aryl halide with alpha-aminobenzyl metal.

DOI： 10.1021/ol802070d

Language：English   Publishing type：Research paper (scientific journal)  

Direct arylation of aryl(azaaryl)methanes with aryl halides takes place at the benzylic position in the presence of a hydroxide base under palladium catalysis to yield triarylmethanes.

DOI： 10.1021/ol0708119

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/anie.200604472

Event date： 2024.9

Language：English   Presentation type：Oral presentation (general)  

Venue：Sheraton Grand Chicago Riverwalk   Country：United States  

Event date： 2024.9

Language：English   Presentation type：Oral presentation (general)  

Venue：Sheraton Grand Chicago Riverwalk   Country：United States  

Language：Japanese  

Country：Japan  

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Country：Japan  

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Rhodium-Catalyzed Reaction of Acylsilanes via Oxidative Addition of Carbonyl Carbon-Silicon Bond

Language：Japanese  

Country：Japan  

ロジウム触媒を用いるビニルシランと配位性官能基を有する有機ハロゲン化物とのクロスカップリング反応

Language：Japanese  

Country：Japan  

Rhodium-Catalyzed Cross-Coupling Reaction of Vinylsilanes Having a Coordination Group with Organic Halides

Language：Japanese  

Country：Japan  

パラジウム触媒によるハロゲン化アリールの2‐ピリジルメチル化反応

Language：Japanese  

Country：Japan  

パラジウム触媒と有機亜鉛反応剤を用いる交差カップリング反応による有機鉄化合物の合成

Language：Japanese  

Country：Japan  

キサントンから誘導したN‐ベンジルイミンのパラジウム触媒によるベンジル位アリール化

Language：Japanese  

Country：Japan  

Palladium-catalyzed benzylic arylation of benzyl sulfones with aryl halides

Language：Japanese  

Country：Japan  

Palladium-catalyzed reaction of 2-(2-hydroxyethyl)pyridine N-oxides with aryl halides

Language：Japanese  

Country：Japan  

連続マイケル反応の開発とbruceantinの不斉全合成研究

Language：Japanese  

Country：Japan  

複数配位子を有する鉄錯体を触媒としたアルケンの不斉エポキシ化反応の開発

Language：Japanese  

Country：Japan  

bruceantinの不斉全合成研究

Language：Japanese  

Country：Other  

Language：Japanese  

Country：Japan  

鉄ポルフィリン様の反応性を示す鉄カルバゾール錯体を用いた触媒的不斉エポキシ化反応

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金(I)触媒による酸化的1,5‐エンイン環化反応を利用したトリシクロ[4.3.0.0^5,7]ノネン骨格の構築

Language：Japanese  

Country：Japan  

Liebeskind‐Srogl‐分子内Diels‐Alder連続反応の開発

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Country：Other  

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Language：Japanese  

Country：Japan  

不斉エポキシ化反応におけるCAZBOX配位子の置換基効果

Language：English  

Country：Japan  

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ホルミルオキシ化を経由した脂環式アルコールの立体化学反転

Language：Japanese  

Country：Japan  

ニッケル・銅共触媒によるフッ化アレーンの脱フッ素ホウ素化反応と¹⁸F‐標識PETプローブ迅速合成法の開発

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Nickel and Copper Co-catalyzed Defluoroborylation of Fluoroarenes for Expeditious Preparation of 18F-Labeled PET Probes

Language：Japanese  

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¹⁸F‐標識PETプローブ超短段階合成のためのフッ化アレーン類の脱フッ素ホウ素化反応

Language：Japanese  

Country：Other  

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ホルミルオキシ化を経由したかさ高い脂環式アルコールの立体化学反転

Language：Japanese  

Country：Japan  

¹⁸F‐標識PETプローブの迅速合成のための遷移金属触媒による脱フッ素ホウ素化反応の開発

Language：English  

Country：Other  

Transition-metal-catalyzed Defluoroborylation of Fluoroarenes for Expeditious Preparation of 18F-Labeled PET Probes

Language：Japanese  

Country：Japan  

ホルミルオキシ化を経由したかさ高い脂環式アルコールの立体化学反転

Language：English  

Country：Other  

Straightforward access to 18F-Labeled PET Probes via Ni/Cu co-catalyzed defluoroborylation of fluoroarenes

Language：Japanese  

Country：Other  

Language：Japanese  

Country：Japan  

銅触媒によるフッ化アレーン類の脱フッ素ホウ素化反応

Language：Japanese  

Country：Japan  

ロジウム触媒を用いたアリールスルフィド類のイプソ位ホウ素化反応

Language：Japanese  

Country：Japan  

ロジウム触媒を用いたカルボン酸の形式的脱炭酸ホウ素化反応

Language：Japanese  

Country：Japan  

炭素‐フッ素結合の化学変換による¹⁸F‐標識PETプローブの迅速合成

Language：Japanese  

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Language：Japanese  

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ロジウム触媒を用いた芳香族カルボン酸の形式的脱炭酸ホウ素化反応

Language：Japanese  

Country：Japan  

フッ化アレーン類の炭素‐フッ素結合の切断を経る触媒的ホウ素化反応

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Cu-catalyzed (multi)borylation of (multi)fluoroarenes via C–F bond cleavage

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Country：Japan  

銅触媒による(マルチ)フッ化アレーン類の(マルチ)脱フッ素ホウ素化反応

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Formal decarboxylative borylation of carboxylic acids via Rh-catalyzed decarbonylative C–C bond cleavage of thioester

Language：Japanese  

Country：Other  

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Country：Other  

Molecular Renovation Strategy: A Novel Synthetic Methodology for Expeditious Development of Molecular Probes

Language：Japanese  

Country：Japan  

ロジウム触媒を用いた芳香族カルボン酸の形式的脱炭酸ホウ素化反応

Language：English  

Country：Other  

Molecular Renovation Strategy: A Novel Synthetic Methodology for Expeditious Development of PET Probes

Language：Japanese  

Country：Other  

Language：Japanese  

Country：Other  

Language：English  

Country：Other  

Molecular Renovation Strategy: A Novel Synthetic Methodology for Expeditious Development of Molecular Probes

Language：Japanese  

Country：Other  

Language：Japanese  

Country：Japan  

銅触媒を用いたgem‐ジフルオロアルケン類の位置選択的脱フッ素ホウ素化反応によるモノフルオロアルケンの合成

Language：Japanese  

Country：Japan  

ロジウム触媒を用いたα,β‐不飽和チオエステルの脱カルボニルホウ素化反応によるビニルホウ素化合物合成法の開発

Language：Japanese  

Country：Japan  

ロジウム触媒を用いたビニルスルフィド類の1,1‐ジボリル化によるgem‐ジボリルアルケンの合成

Language：Japanese  

Country：Japan  

パラジウム錯体を用いるアリールボロン酸誘導体の¹¹C‐シアノ化反応

Language：English  

Country：Germany  

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Country：Other  

Copper-Catalyzed ipso-Borylation of Fluoroarenes

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Country：Other  

Language：Japanese  

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Country：Japan  

アルケニルスルフィド類の炭素‐硫黄結合の切断を経るロジウム触媒を用いた1,1‐ジボリル化反応の開発

Language：Japanese  

Country：Other  

Language：English  

Country：Other  

Molecular Renovation Strategy: A Novel Synthetic Methodology for Expeditious Development of Molecular Probes

Language：Japanese  

Country：Japan  

銅触媒を用いた2,2‐ジフルオロビニルアレーン類のトランス位選択的脱フッ素ホウ素化反応の開発

Language：Japanese  

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Molecular Renovation Strategy: A Novel Synthetic Methodology for Expeditious Development of Molecular Probes

Language：English  

Country：Other  

Copper-Catalyzed Defluoroborylation of Fluoroarenes and gem-Difluoroalkenes

Language：Japanese  

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Language：English  

Country：Other  

“Molecular Renovation Strategy: A Novel Synthetic Methodology for Expeditious Development of Molecular Probes

Language：English  

Country：Other  

Copper-Catalyzed Defluoroborylation of Fluoroarenes and gem-Difluoroalkenes

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Country：Other  

Copper-Catalysed regioselective monodefluoroborylation of gem-Difluoroalkenes for facile preparation of monofluoroalkene mimics

Language：Japanese  

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Country：Other  

Synthesis of a Fluoroalkene Mimic of an Amide Drug via Copper-Catalyzed Defluoroborylation of (2,2-Difluorovinyl)arenes

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Development of a synthetic building block for fluoroalkenes by Cu-catalyzed defluoroborylation

Language：Japanese  

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Country：China  

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Country：China  

Language：Japanese  

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Language：Japanese  

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Country：Japan  

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Country：Japan  

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Country：China  

Language：Japanese  

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Country：Germany  

Language：Japanese  

Country：Japan  

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Country：Poland  

Language：English  

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Country：Australia  

Language：English  

Country：Korea, Republic of  

Language：English  

Country：Korea, Republic of  

Language：Japanese  

Country：Japan  

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Country：Japan  

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Language：English  

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Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：関⻄学院大学三田キャンパス  

Language：Japanese   Presentation type：Poster presentation  

Venue：星薬科大学百年記念館  

Language：Japanese   Presentation type：Poster presentation  

Venue：星薬科大学百年記念館  

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：九州地区国立大学 九重共同研修所  

Language：Japanese   Presentation type：Poster presentation  

Venue：星薬科大学百年記念館  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：熊本城ホール  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：熊本城ホール  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：熊本城ホール  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：つくば国際会議場  

Language：Japanese   Presentation type：Poster presentation  

Venue：タワーホール船橋  

Language：Japanese   Presentation type：Poster presentation  

Venue：タワーホール船橋  

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：Seoul National University Hospital   Country：Korea, Republic of  

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Language：Others  

Language：English  

DOI： 10.1246/bcsj.20190310

Language：Japanese  

Defluoroborylation Reactions of Fluoroarenes
Fluoroarenes are widely found in molecules involving pharmaceuticals, agrochemicals, and organic functional materials. The fluoro group is often installed to the molecules to provide favorable characteristics that rest on unique properties of fluorine. The increasing availability of fluoroarenes has stimulated considerable interest in their late-stage transformation via C-F bond cleavage, which is a challenging issue to achieve due to high stability of the C-F bond. Particularly, defluoroborylation of fluoroarenes has been attracting much attention owing to the reliable and versatile organoboron chemistries that enable facile diversification for obtaining valuable compounds such as drug candidates and molecular probes that promote researches in drug discovery and life science. In this article is reviewed the recent progress made on this challenging issue. These include borylation of perfluoroarenes having a fluoro group with relatively high leaving ability, low-valent transition metal-catalyzed defluoroborylation of fluoroarenes bearing an inert C-F bond, and promising photochemical defluoroborylation of fluoroarenes.

DOI： 10.5059/yukigoseikyokaishi.77.883

Language：Japanese  

Language：Japanese  

医薬品をPETプローブに作り変える分子リノベーション技術の開発

Language：Japanese  

Language：Japanese  

ロジウム触媒を用いたビニルスルフィド類のジボリル化反応によるgem‐ジボリルアルケン合成

Language：English  

Development of Small Molecule-Based PET Probes
<p>PET (Positron Emission Tomography) is a less-invasive molecular imaging method that is used for clinical diagnosis and evaluation of drug candidates at the early stage of drug development. This article reviews recent achievements on PET chemistry with a focus on the development of PET probes, particularly for small molecules labeled with a short-lived positron-emitting radionuclide such as carbon-11 or fluorine-18.</p>

DOI： 10.2530/jslsm.jslsm-37_0038

Language：Japanese  

低分子PETプローブの開発
<p>PET (Positron Emission Tomography) is a less-invasive molecular imaging method that is used for clinical diagnosis and evaluation of drug candidates at the early stage of drug development. This article reviews recent achievements on PET chemistry with a focus on the development of PET probes, particularly for small molecules labeled with a short-lived positron-emitting radionuclide such as carbon-11 or fluorine-18.</p>

DOI： 10.2530/jslsm.jslsm-37_0038

Language：Japanese  

次世代生命基盤技術を用いたB型肝炎制圧のための創薬研究 PET分子イメージングによる薬効評価・薬物動態研究

Language：Japanese  

[18F]芳香族フッ化物の革新的合成法

Language：Japanese  

Methanol for a Material for Organic Chemistry

Language：Japanese  

Synthetic Organic Reactions with Photoredox Catalysis and Visible Light
Photochemical reactions have been attracting increasing attention owing to their efficiency and inherent sustainability However the photochemical reactions have provided few practical reactions for organic synthesis so far This short review provides a recent development of organic reactions with photoredox catalysis which allows various transformations practically with visible light

DOI： 10.5059/yukigoseikyokaishi.68.1307

Language：Japanese  

Study Abroad at Ritter Lab, Harvard Univ.

Type：Competition, symposium, etc. 

Number of participants：150

Type：Competition, symposium, etc. 

Number of participants：10,000

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Number of participants：150

Type：Academic society, research group, etc. 

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：20

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Competition, symposium, etc. 

Number of participants：200

Type：Competition, symposium, etc. 

Number of participants：200

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：28

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Competition, symposium, etc. 

Number of participants：100

Type：Competition, symposium, etc. 

Number of participants：80

Type：Competition, symposium, etc. 

Number of participants：200

Type：Competition, symposium, etc. 

Number of participants：200

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：26

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：21

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Competition, symposium, etc. 

Number of participants：200

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：34

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Competition, symposium, etc. 

Number of participants：200

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：33

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Competition, symposium, etc. 

Number of participants：500

Type：Competition, symposium, etc. 

Number of participants：200

Type：Competition, symposium, etc. 

Number of participants：30

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：25

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Competition, symposium, etc. 

Number of participants：200

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：10

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：2

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：2

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

Type：Competition, symposium, etc. 

Number of participants：17

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：1

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0