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)tiop...

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Bibliographic Details
Published in:	European journal of medicinal chemistry Vol. 41; no. 10; pp. 1196 - 1200
Main Authors:	Rando, D.G., Doriguetto, A.C., Tomich de Paula da Silva, C.H., Ellena, J., Sato, D.N., Leite, C.Q.F., Varanda, E.A., Ferreira, E.I.
Format:	Journal Article
Language:	English
Published:	Oxford Elsevier Masson SAS 01-10-2006 Elsevier
Subjects:	Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antimycobacterial activity Antitubercular Agents - chemical synthesis Antitubercular Agents - chemistry Antitubercular Agents - pharmacology Biological and medical sciences Chemical mutagenesis Crystallography, X-Ray Medical sciences Microbial Sensitivity Tests Models, Molecular Molecular Structure Mutagenicity Mycobacterium avium - drug effects Mycobacterium kansasii - drug effects Nitro Compounds - chemical synthesis Nitro Compounds - chemistry Nitro Compounds - pharmacology Nitrotienyl derivative Pharmacology. Drug treatments Potential antimycobacterial agent Structure-Activity Relationship Thiophenes - chemical synthesis Thiophenes - chemistry Thiophenes - pharmacology Toxicology X-ray structure determination Potential antimycobacterial agent X-ray structure determination Mutagenicity Nitrotienyl derivative Antimycobacterial activity Nitro compound Five membered ring Toxicity Mutagen Salmonella typhimurium Bacteria Antituberculous agent Chemical synthesis Enterobacteriaceae Mutagenicity testing Mycobacterium avium Azine X ray diffraction In vitro Biological activity Sulfur heterocycle Mycobacterium tuberculosis Mycobacteriales Mycobacteriaceae Actinomycetes Antibacterial agent Crystalline structure
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Summary:	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. kansasei, although it had a high level of mutagenicity, as observed in mutagenic activity tests.
ISSN:	0223-5234 1768-3254
DOI:	10.1016/j.ejmech.2006.04.009