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