title: Synthesis of new 2-thio-[1,2,4]triazolo[1,5-c]quinazoline derivatives and its antimicrobial activity.
abstract: 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.affiliation: Department of Pharmaceutical Chemistry, Zaporozhye State Medical University, 69035 Zaporozhye, Ukraine.
authors.forename: Lyudmila
authors.initials: L
authors.lastname: Antipenko
authors.forename: Alexander
authors.initials: A
authors.lastname: Karpenko
authors.forename: Sergey
authors.initials: S
authors.lastname: Kovalenko
authors.forename: Andrew
authors.initials: A
authors.lastname: Katsev
authors.forename: Elena
authors.initials: E
authors.lastname: Komarovska-Porokhnyavets
authors.forename: Vladimir
authors.initials: V
authors.lastname: Novikov
authors.forename: Aleksey
authors.initials: A
authors.lastname: Chekotilo
mesh_terms: 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
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D007202:Indicators and Reagents; D008055:Lipids; D011799:Quinazolines