A duplicated nitrotienyl derivative with antimycobacterial activity: synthesis, X-ray crystallography, biological and mutagenic activity tests.
A duplicated nitrotienyl derivative was obtained as a by-product from the synthesis of a proposed molecular hybrid of a nitrotienyl derivative and isoniazid with an expected dual antimycobacteria mechanism. The structure was shown to be the 5,5'-dinitro-2-(2,3-diaza-4-(2'-tienyl)buta-1,3-dienyl)tiophene by X-ray crystallography. The minimal inhibitory concentration (MIC) determination of this compound proved to be promising against Mycobacterium pathogenic strains such as M. avium and M. kansasii, although it had a high level of mutagenicity, as observed in mutagenic activity tests.
Rando
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DG
Faculdade de Ciências Farmacêuticas, Universidade de São Paulo - Av. Prof. Lineu Prestes, 580, CEP 05508-900, São Paulo, SP, Brazil.
Doriguetto
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AC
Tomich de Paula da Silva
C H
CH
Ellena
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J
Sato
D N
DN
Leite
C Q F
CQ
Varanda
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EA
Ferreira
E I
EI
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D009162:Mycobacterium avium / Q000187:drug effects*; D019909:Mycobacterium kansasii / Q000187:drug effects*; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C516490:5,5'-dinitro-2-(2,3-diaza-4-(2'-tienyl)buta-1,3-dienyl)tiophene; D000995:Antitubercular Agents; D009574:Nitro Compounds; D013876:Thiophenes