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ID 34212
フルテキストURL
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著者
Ali, Hamed I. Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
Ashida, Noriyuki Biology Laboratory, Research and Development Division, Yamasa Shoyu Co.
Nagamatsu, Tomohisa Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
抄録
Various novel 10-alkyl-2-deoxo-2-methylthioflavin-5-oxides and their 2-alkylamino derivatives were prepared by facile nitrosative cyclization of 6-(N-alkylanilino)-2-methylthiopyrimidin-4(3H)-ones followed by nucleophilic replacement of the 2-methylthio moiety by different amines, and acidic hydrolysis of the 2-methylthio moiety afforded the corresponding flavin derivatives. 2-Deoxo-2-methylthio-5-deazaalloxazines and 2-deoxo-2-methylthioalloxazine-5-oxides were also prepared by Vilsmeier reaction and by nitrosation of 6-anilino-2-methylthiopyrimidin-4(3H)-ones, respectively. Then, they were subjected to nucleophilic replacement with appropriate amines to produce the corresponding 2-alkylamino derivatives. Regiospecific N-3-alkylation of 2-deoxo-2-methylthioalloxazine-5-oxides was carried out with various alkylating agents in the usual way, The antitumor activities against CCRF-HSB-2 and KB tumor cells have been investigated in vitro, and many compounds showed promising antitumor activities. Furthermore, AutoDock molecular docking into PTK (PDB: 1t46) has been done for lead optimization of the aforementioned compounds as potential PTK inhibitors.
キーワード
antitumor activity
flavin-5-oxide
alloxazine-5-oxide
AutoDock
備考
Published with permission from the copyright holder.
This is a author's copy,as published in Bioorganic & Medicinal Chemistry , 2008 Vol.16 Issue.2 pp.922-940
Publisher URL: http://dx.doi.org/10.1016/j.bmc.2007.10.014
Direct access to Thomson Web of Science record
Copyright © 2007 by Elsevier Ltd.
発行日
2008-01-15
出版物タイトル
Bioorganic & Medicinal Chemistry
16巻
2号
出版者
Pergamon-Elsevier Science Ltd.
開始ページ
922
終了ページ
940
ISSN
0968-0896
NCID
AA10938083
資料タイプ
学術雑誌論文
言語
English
著作権者
Elsevier Ltd.
論文のバージョン
author
査読
有り
DOI
PubMed ID
Web of Sience KeyUT
Submission Path
organic_chemistry/13