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ID 34212
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Author
Ali, Hamed I.
Ashida, Noriyuki
Abstract
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.
Keywords
antitumor activity
flavin-5-oxide
alloxazine-5-oxide
AutoDock
Note
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.
Published Date
2008-01-15
Publication Title
Bioorganic & Medicinal Chemistry
Volume
volume16
Issue
issue2
Publisher
Pergamon-Elsevier Science Ltd.
Start Page
922
End Page
940
ISSN
0968-0896
NCID
AA10938083
Content Type
Journal Article
language
英語
Copyright Holders
Elsevier Ltd.
File Version
author
Refereed
True
DOI
PubMed ID
Web of Sience KeyUT
Submission Path
organic_chemistry/13