Basic Research on Amide-based Axial Chirality and Development to Medicinal Chemistry
| Project/Area Number |
25460154
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Drug development chemistry
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| Research Institution | Teikyo University |
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Principal Investigator |
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| Co-Investigator(Renkei-kenkyūsha) |
TABATA HIDETSUGU 帝京大学, 薬学部, 講師 (80445634)
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| Project Period (FY) |
2013-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
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| Keywords | 軸不斉 / 立体化学 / キラリティー / ベンゾジアゼピン / バソプレシン / バソプレッシン / ベンゾアゼピン / ベンゾチアゼピン / バソプレシン受容体拮抗薬 / S-オキシド / 中心不斉 / アミド / ベンゾラクタ |
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| Outline of Final Research Achievements |
Aryl amides and anilides, which exist in many biologically active molecules as parts of the pharmacophore, possess sp2-sp2 atropisomerism based on the aryl-amide axis. Although often overlooked, such atropisomerisms are latent in many organic molecules. When exerting biological activity, the receptors and enzymes should recognize the specific conformation of themolecules. In this study, conformational change of the benzo-fused seven-membered-ring nitrogen heterocycles, which have been used as important core structures of various biologically active molecules, was studied in relation to the biological activity. Especially, the active form of the tolvaptan-type vasopressin antagonist was examined in detail to reveal the axial chirality plays a more important role than the central chirality at C5 in receptor recognition. The study also revealed that N-sulfonyl-1,5-benzodiazepines also possess sp2-sp2 atropisomerism based on the aryl-N(SO2) axis.
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Report
(5 results)
Research Products
(39 results)
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[Journal Article] Conoformation and atropisomeric properties of indometacin derivatives2013
Author(s)
Shintaro Wakamatsu, Yuka Takahashi, Hidetsugu Tabata, Tetsuta Oshitari, Norihiko Tani, Isao Azumaya, Yukiteru Katsumoto, Takeyuki Tanaka, Shinzo Hosoi, Hideaki Natsugari, Hideyo Takahashi
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Journal Title
Chemistry A European Journal
Volume: 19
Issue: 22
Pages: 7056-7063
DOI
Related Report
Peer Reviewed
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