Synthesis and antitubercular activity of 3-aryl substituted-2-[1H(2H)benzotriazol-1(2)-yl]acrylonitriles.
A series of 22 3-aryl substituted-2-(1H(2H)-benzotriazol-1(2)-yl)acrylonitriles was synthesized for a preliminary in vitro evaluation of antitubercular activity according to an international program with the Tuberculosis Antimicrobial Acquisition & Coordinating Facility (TAACF). This work reports the synthetic approach and analytical and spectroscopic characterization (UV, IR, 1H- and 13C-NMR) of all compounds synthesized. Several compounds showed an interesting activity in the preliminary screening with a percent growth inhibition of the virulent Mycobacterium tuberculosis between 40 and 99% at the concentration of 12.5 microg/mL. The most effective derivatives E-5a and E-5e were also tested against M. avium in vitro.
Sanna
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Dipartimento Farmaco-Chimico-Tossicologico, via Muroni 23/a, 07100, Sassari, Italy. psanna@ssmainuniss.it
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Nikookar
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D000181:Acrylonitrile / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects* / Q000472:pathogenicity; D009570:Nitriles / Q000138:chemical synthesis / Q000494:pharmacology; D013053:Spectrophotometry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
C412315:2-(1H-benzotriazol-1-yl)-3-(4-bromophenyl)acrylonitrile; C412314:2-(1H-benzotriazol-1-yl)-3-phenylacrylonitrile; D000995:Antitubercular Agents; D009570:Nitriles; D014230:Triazoles; C012771:benzotriazole; D000181:Acrylonitrile