Document Detail


Synthesis of new 2-thio-[1,2,4]triazolo[1,5-c]quinazoline derivatives and its antimicrobial activity.
MedLine Citation:
PMID:  19483337     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A series of novel ([1,2,4]triazolo[1,5-c]quinazolin-2-ylthio)carboxylic acids 2a-d and esters 3a-l were synthesized and evaluated for antimicrobial activity. Alkylation of potassium 2-thio-[1,2,4]triazolo[1,5-c]quinazoline 1 with halogenocarboxylic acids and its esters proceeded S-regioselectively. During acid catalyzed esterification of 2a-c, degradation of the pyrimidine ring was observed. The structures of the compounds were elucidated by FT-IR, (1)H- and (13)C-NMR, electron impact mass spectra (EI-MS) and LC-MS spectral data. Antimicrobial and antifungal activity of synthesized compounds was tested against Escherichia coli, Pseudomonas aeruginosa, Aspergillus niger, Mycobacterium luteum, Candida albicans and Candida tenuis. Acids 2a and 2c exhibited significant activity against C. albicans, which was additionally confirmed by the bioluminescence inhibition test and interrelated with their lipophilicity.
Authors:
Lyudmila Antipenko; Alexander Karpenko; Sergey Kovalenko; Andrew Katsev; Elena Komarovska-Porokhnyavets; Vladimir Novikov; Aleksey Chekotilo
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  57     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  2009 Jun 
Date Detail:
Created Date:  2009-06-01     Completed Date:  2009-07-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  580-5     Citation Subset:  IM    
Affiliation:
Department of Pharmaceutical Chemistry, Zaporozhye State Medical University, 69035 Zaporozhye, Ukraine.
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MeSH Terms
Descriptor/Qualifier:
Anti-Bacterial Agents / chemical synthesis,  pharmacology
Anti-Infective Agents / chemical synthesis*,  chemistry,  pharmacology*
Antifungal Agents / chemical synthesis,  pharmacology
Bacteria / drug effects
Fungi / drug effects
Indicators and Reagents
Lipids / chemistry
Luminescence
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Photobacterium / drug effects
Quinazolines / chemical synthesis*,  pharmacology*
Solubility
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Spectroscopy, Fourier Transform Infrared
Chemical
Reg. No./Substance:
0/Anti-Bacterial Agents; 0/Anti-Infective Agents; 0/Antifungal Agents; 0/Indicators and Reagents; 0/Lipids; 0/Quinazolines

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