Document Detail

Antitumor studies. part 3: design, synthesis, antitumor activity, and molecular docking study of novel 2-methylthio-, 2-amino-, and 2-(N-substituted amino)-10-alkyl-2-deoxo-5-deazaflavins.
MedLine Citation:
PMID:  17644399     Owner:  NLM     Status:  MEDLINE    
Various novel 10-alkyl-2-deoxo-2-methylthio-5-deazaflavins have been synthesized by reaction of 6-(N-alkylanilino)-2-methylthiopyrimidin-4(3H)-ones with Vilsmeier reagent. The similar 2-(N-substituted amino) derivatives were prepared by nucleophilic replacement reaction of the 2-methylthio moiety by appropriate amines. The 2-oxo derivatives (i.e., 5-deazaflavins) were obtained by acidic hydrolysis of the 2-methylthio derivatives. The antitumor activities against CCRF-HSB-2 and KB cells and the antiviral activities against HSV-1 and HSV-2 have been investigated in vitro, and many compounds showed promising antitumor activities. Furthermore, AutoDock molecular docking into PTK has been done for lead optimization of these compounds as potential PTK inhibitors. Whereas, the designed 2-deoxo-5-deazaflavins connected with amino acids at the 2-position exhibited the good binding affinities into PTK with more hydrogen bonds.
Hamed I Ali; Noriyuki Ashida; Tomohisa Nagamatsu
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Publication Detail:
Type:  Journal Article     Date:  2007-07-04
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  15     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2007 Oct 
Date Detail:
Created Date:  2007-08-13     Completed Date:  2007-12-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  6336-52     Citation Subset:  IM    
Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University 1-1-1, Tsushima-Naka, Okayama 700-8530, Japan.
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MeSH Terms
Amino Acids / chemistry
Antineoplastic Agents / chemical synthesis,  pharmacology*
Antiviral Agents / chemical synthesis,  pharmacology*
Binding Sites
Cell Line, Tumor / drug effects
Drug Design*
Drug Screening Assays, Antitumor
Flavins / chemical synthesis,  pharmacology*
Hydrogen Bonding
Inhibitory Concentration 50
Spectrophotometry, Ultraviolet
Structure-Activity Relationship
Time Factors
Reg. No./Substance:
0/Amino Acids; 0/Antineoplastic Agents; 0/Antiviral Agents; 0/Flavins

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