論文 - 柴田 哲男
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Iodoarene-catalyzed fluorination and aminofluorination by Ar-I/HF•pyridine/mCPBA system 査読あり
Satoru Suzuki, Tomohiro Kamo, Kazunobu Fukushi, Takaaki Hiramatsu, Etsuko Tokunaga, Toshifumi Dohi, Yasuyuki Kita, Norio Shibata
Chemical Science 5 ( 7 ) 2754 - 2760 2014年03月
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
We have developed iodoarene-catalyzed nucleophilic fluorination of β-dicarbonyl compounds and intramolecular aminofluorination of ω-amino-alkenes using the same reaction condition. The key for this reaction is the in situ generation of a hypervalent iodine compound ArIF2 by hydrogen fluoride, mCPBA and a catalytic amount of iodoarene. Preliminary trials of catalytic asymmetric nucleophilic fluorination were conducted.
DOI： 10.1039/C3SC53107D
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Bis(pentafluorosulfanyl)phenyl Azide as an Expeditious Tool for Click Chemistry toward Antitumor Pharmaceuticals 招待あり 査読あり
Yu-Dong Yang, Etsuko Tokunaga,Hidehiko Akiyama Norimichi Saito and Norio Shibata
ChemMedChem 9 ( 5 ) 913 - 917 2014年03月
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
The inclusion of fluorine in pharmaceutical agents is a well- established means of improving their druglike properties. Different substituents have been used to introduce fluorine, including trifluoromethyl and trifluoromethylthio groups; however, the pentafluorosulfanyl remains relatively underutilized although it is considered to be a “super” trifluoromethyl group. Here, a series of pentafluorosulfanyl-containing 1,4-disubstituted-1,2,3-triazoles were synthesized by click reaction from alkynes and 3,5-bis(pentafluorosulfanyl)phenyl azide in excellent yields. Their biological activities were evaluated against human leukemic monocyte lymphoma U937 cells. In particular, 1-(3,5-bis(pentafluorosulfanyl)phenyl)-4-(4-fluorophenyl)-1H-1,2,3-triazole exhibited potent efficacy in cell viability assays at a concentration of 60 μM and was shown to activate caspase-3 activity, indicating induction of apoptosis. An analogous fluorenol-substituted triazole also exhibited promising cytotoxic effects against U937 cells, with an IC50 value of 6.29 μM. Given these preliminary results, these pentafluorosulfanyl-containing triazoles represent useful building blocks for the further development of novel antitumor agents.
その他リンク： http://onlinelibrary.wiley.com/doi/10.1002/cmdc.201400059/abstract
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Diastereoselective Additive Trifluoromethylation/Halogenation of Isoxazole Triflones: Synthesis of All-carbon Functionalized Trifluoromethyl Isoxazoline Triflones 査読あり
Hiroyuki Kawai, Yutaka Sugita, Etsuko Tokunaga, Hiroyasu Sato, Motoo Shiro, Norio Shibata
ChemistryOpen 3 ( 1 ) 14 - 18 2014年02月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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A phthalocyanine–subphthalocyanine heterodinuclear dimer: comparison of spectroscopic properties with those of homodinuclear dimers of constituting units 査読あり
Norio Shibata, Satoru Mori, Masamichi Hayashi, Masashi Umeda, Etsuko Tokunaga, Motoo Shiro, Hiroyasu Sato, Tomonori Hoshi, Nagao Kobayashi
Chemical Communications 50 ( 23 ) 3040 - 3043 2014年01月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1039/C3CC49831J
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Thalidomide Increases Human Hepatic Cytochrome P450 3A Enzymes by Direct Activation of the Pregnane X Receptor 査読あり
Norie Murayama, Rinie van Beuningen, Hiroshi Suemizu, Christiane Guguen-Guillouzo, Norio Shibata, Kanako Yajima, Masahiro Utoh, Makiko Shimizu, Christophe Chesné, Masato Nakamura, F. Peter Guengerich, René Houtman, Hiroshi Yamazaki
Chemical Research in Toxicology 27 ( 2 ) 304 - 308 2014年01月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1021/tx4004374
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S-((Phenylsulfonyl)difluoromethyl)thiophenium Salts: Carbon-Selective Electrophilic Difluoromethylation of β-Ketoesters, β-Diketones, and Dicyanoalkylidenes 査読あり
Xin Wang, Guokai Liu, Xiu-Hua Xu, Naoyuki Shibata, Etsuko Tokunaga, Norio Shibata
Angewandte Chemie International Edition 53 ( 7 ) 1827 - 1831 2014年01月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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New Approaches to the Regioselective Synthesis of Heteroaryl Triflones 査読あり
Xiu-Hua Xu, Norio Shibata
有機合成化学協会誌（Yuki Gosei Kagaku Kyokaishi） 71 ( 11 ) 1195 - 1201 2013年12月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Human Cytochrome P450 Oxidation of 5-Hydroxythalidomide and Pomalidomide, an Amino Analogue of Thalidomide 査読あり
Goutam Chowdhury, Norio Shibata, Hiroshi Yamazaki, F. Peter Guengerich
Chemical Research in Toxicology 27 ( 1 ) 147 - 156 2013年12月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1021/tx4004215
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Asymmetric Mannich reaction between (S)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine and malonic acid derivatives. Stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids 査読あり
Norio Shibata, Takayuki Nishimine, Naoyuki Shibata, Etsuko Tokunaga, Kosuke Kawada, Takumi Kagawa, José Luis Aceña, Alexander E. Sorochinsky, Vadim A. Soloshonok
Organic and Biomolecular Chemistry 12 ( 9 ) 1454 - 1462 2013年12月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1039/C3OB42425A
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NH-type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications 査読あり
Mackenzie Bergagnini, Kazunobu Fukushi, Jianlin Han, Norio Shibata, Christian Roussel, Trevor K. Ellis, José Luis Aceña, Vadim A. Soloshonok
Organic and Biomolecular Chemistry 12 ( 8 ) 1278 - 1291 2013年12月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1039/C3OB41959B
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フッ素化学の錬金術：フッ素樹脂副産物フルオロホルムの医薬品原料・液晶材料への活用 査読あり
柴田哲男，杉田豊，河合洋幸
ファインケミカル 42 ( 11 ) 48 - 55 2013年11月
記述言語：日本語 掲載種別：研究論文（学術雑誌）
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Kinetic Resolution of Allylic Fluorides by Enantioselective Allylic Trifluoromethylation based on Silicon-assisted C-F Bond Cleavage 査読あり
Takayuki Nishimine, Kazunobu Fukushi, Naoyuki Shibata, Hiromi Taira, Etsuko Tokunaga, Akihito Yamano, Motoo Shiro, Norio Shibata
Angewandte Chemie International Edition 53 ( 2 ) 517 - 520 2013年11月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Regioselective 1,4-Trifluoromethylation of α, β-Unsaturated Ketones via a S-(trifluoromethyl)diphenylsulfonium salts/Copper System 査読あり
Satoshi Okusu, Yutaka Sugita, Etsuko Tokunaga, Norio Shibata
Beilstein Journal of Organic Chemistry 9 2189 - 2193 2013年10月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.3762/bjoc.9.257
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Stereoselective Synthesis of Vinyl Triflones and Heteroaryl Triflones via Anionic O->Cvinyl and N->Cvinyl Trifluoromethanesulfonyl Migration Reactions 査読あり
Xiu-Hua Xu, Misaki Taniguchi, Xin Wang, Etsuko Tokunaga, Tomohiro Ozawa, Hideki Masuda, Norio Shibata
Angewandte Chemie International Edition 52 ( 48 ) 12628 - 12631 2013年10月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Enantioselective monofluoromethylation of aldehydes with 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide catalyzed by a bifunctional cinchona alkaloid-derived thiourea-titanium complex 査読あり
Hai Ma, Kohei Matsuzaki, Yu-Dong Yang, Etsuko Tokunaga, Daisuke Nakane, Tomohiro Ozawa, Hideki Masuda, Norio Shibata
Chemical Communications 49 ( 95 ) 11206 - 11208 2013年10月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1039/C3CC46544F
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Enantioselective Synthesis of 5-Trifluoromethyl-2-isoxazolines and Their N-Oxides by [Hydroxy(tosyloxy)iodo]benzene-Mediated Oxidative N–O Coupling 査読あり
Hiroyuki Kawai, Satoshi Okusu, Etsuko Tokunaga, Norio Shibata
European Journal of Organic Chemistry 2013 ( 29 ) 6506 - 6509 2013年09月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Chiral N-Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination 査読あり
Chuan-Le Zhu, Mayaka Maeno, Fa-Guang Zhang, Taiki Shigehiro, Takumi Kagawa, Kosuke Kawada, Norio Shibata, Jun-An Ma, Dominique Cahard
European Journal of Organic Chemistry 2013 ( 29 ) 6501 - 6505 2013年09月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Redox chemistry of trifluoromethyl sulfonium salts as CF3 radical sources 査読あり
Satoshi Mizuta, Stefan Verhoog, Xin Wang, Norio Shibata, Véronique Gouverneur, Maurice Médebielle
Journal of Fluorine Chemistry 155 124 - 131 2013年07月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Highly Enantioselective Monofluoromethylation of C2-Arylindoles Using FBSM under Chiral Phase-Transfer Catalysis 査読あり
Kohei Matsuzaki, Tatsuya Furukawa, Etsuko Tokunaga, Takashi Matsumoto, Motoo Shiro, Norio Shibata
Organic Letters 15 ( 13 ) 3282 - 3285 2013年06月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1021/ol4013102
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Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Copper-Catalyzed Trifluoromethylthiolation of Enamines, Indoles, and β-Keto Esters 査読あり
Yu-Dong Yang, Ayaka Azuma, Etsuko Tokunaga, Mikio Yamasaki, Motoo Shiro, Norio Shibata
Journal of the American Chemical Society 135 ( 24 ) 8782 - 8785 2013年06月
記述言語：英語 掲載種別：研究論文（学術雑誌）
DOI： 10.1021/ja402455f
