Synthesis of new 2-thio-[1,2,4]triazolo[1,5-c]quinazoline derivatives and its antimicrobial activity.
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.
Antipenko
Lyudmila
L
Department of Pharmaceutical Chemistry, Zaporozhye State Medical University, 69035 Zaporozhye, Ukraine.
Karpenko
Alexander
A
Kovalenko
Sergey
S
Katsev
Andrew
A
Komarovska-Porokhnyavets
Elena
E
Novikov
Vladimir
V
Chekotilo
Aleksey
A
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D007202:Indicators and Reagents; D008055:Lipids / Q000737:chemistry; D049449:Luminescence; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010776:Photobacterium / Q000187:drug effects; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D007202:Indicators and Reagents; D008055:Lipids; D011799:Quinazolines