城西大学機関リポジトリJURASynthesis and biological evaluation of 3-styrylchromone derivatives as selective monoamine oxidase B inhibitors

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Synthesis and biological evaluation of 3-styrylchromone derivatives as selective monoamine oxidase B inhibitors

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ID	JOS-j.bmc.2021.116255
著者：名前	高尾, 浩一/竹村, 友里/永井, 純子/鎌内, 等/星, かおり/馬橋, 遼/植沢, 芳広/杉田, 義昭
著者：別形式	Takao, Koichi / Takemura, Yuri / Nagai, Junko / Kamauchi, Hitoshi / Hoshi, Kaori / Mabashi, Ryo / Uesawa, Yoshihiro / Sugita, Yoshiaki
著者：カナ	タカオ, コウイチ/タケムラ, ユリ/ナガイ, ジュンコ/カマウチ, ヒトシ/ホシ, カオリ/マバシ, リョウ/ウエサワ, ヨシヒロ/スギタ, ヨシアキ
著者：所属	城西大学薬学部薬科学科生物有機化学研究室 / 城西大学薬学部薬科学科生物有機化学研究室 / 明治薬科大学医療分子解析学研究室 / 城西大学薬学部薬科学科生物有機化学研究室 / J城西大学薬学部薬科学科生物有機化学研究室 / 城西大学薬学部薬科学科生物有機化学研究室 / 明治薬科大学医療分子解析学研究室 / 城西大学薬学部薬科学科生物有機化学研究室
著者：所属(別形式）	Josai University, Faculty of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Laboratory of Bioorganic Chemistry / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Laboratory of Bioorganic Chemistry / Meiji Pharmaceutical University, Department of Medical Molecular Informatics / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Laboratory of Bioorganic Chemistry / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Laboratory of Bioorganic Chemistry / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Laboratory of Bioorganic Chemistry / Meiji Pharmaceutical University, Department of Medical Molecular Informatics / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Laboratory of Bioorganic Chemistry
著者版フラグ	author
出版者	Elsevier
冊子ISSN	09680896
電子ISSN	14643391
掲載誌名	Bioorganic and Medicinal Chemistry
巻	42
刊行年月	2021-07
開始ページ	1
終了ページ	9
コンテンツ作成日	2021-03-08
コンテンツ修正日	2021-05-28
コンテンツ登録日	2023-07-27
識別番号：DOI	info:doi/10.1016/j.bmc.2021.116255
識別番号：DOI（リンク）	https://doi.org/10.1016/j.bmc.2021.116255
PubMed番号	34119696
抄録	A series of 3-styrylchromone derivatives was synthesized and evaluated for monoamine oxidase (MAO) A and B inhibitory activities. Most of all derivatives inhibited MAO-B selectively, except compound 21. Compound 19, which had a methoxy group at R2 on the chromone ring and chlorine at R4 on phenyl ring, potently inhibited MAO-B, with an IC50 value of 2.2 nM. Compound 1 showed the highest MAO-B selectivity, with a selectivity index of >3700. Further analysis of these compounds indicated that compounds 1 and 19 were reversible and mixed-type MAO-B inhibitors, suggesting that their mode of action may be through tight-binding inhibition to MAO-B.Quantitative structure–activity relationship (QSAR) analyses of the 3-styrylchromone derivatives were conducted using their pIC50 values, through Molecular Operating Environment (MOE) and Dragon. There were 1796 descriptors of MAO-B inhibitory activity, which showed significant correlations (P < 0.05). Further investigation of the 3-styrylchromone structures as useful scaffolds was performed through three-dimensional-QSAR studies using AutoGPA, which is based on the molecular field analysis algorithm using MOE. The MAO-B inhibitory activity model constructed using pIC50 value index exhibited a determination coefficients (R2) of 0.972 and a Leave-One-Out cross-validated determination coefficients (Q2) of 0.914.These data suggest that the 3-styrylchromone derivatives assessed herein may be suitable for the design and development of novel MAO inhibitors.
キーワード	3-Styrylchromone/Monoamine oxidase-A/Monoamine oxidase-B/Quantitative structure–activity relationship/QSAR/Molecular Operating Environment MOE/AuroGPA
注記	Article No.175068
言語	eng
資源タイプ	text
ジャンル	01学術雑誌論文 / Journal Article
フォーマット	application/pdf
権利	Copyright © 2021 Elsevier Ltd.
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このアイテムを表示する：URI	https://libir.josai.ac.jp/il/meta_pub/G0000284repository_JOS-j.bmc.2021.116255

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