Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: Synthesis, biological evaluation, lipophilicity, and conformational studies
2008
Authors:
Ezabadi, Iraj RahaviCamoutsis, Charalabos
Zoumpoulakis, Panagiotis
Geronikaki, Athina
Soković, Marina
Glamočlija, Jasmina
Ćirić, Ana
Document Type:
Article (Published version)
,
© 2007 Elsevier Ltd.
Metadata
Show full item recordAbstract:
A series of 10 new 5-[2-(substituted sulfamoyl)-4,5-dimethoxy-benzyl]-4aryl-s-triazole-3-thiones were synthesized and evaluated for in vitro antifungal and antibacterial activity. All compounds tested showed significant antifungal activity against all the micromycetes, compared to the commercial fungicide bifonazole. Differences in their activity depend on the substitution of different reactive groups. More specifically, best antifungal activity among synthetic analogues was shown with N-dimethylsulfamoyl group. All the compounds tested against bacteria showed the same activity as the commercial agent streptomycin, except for Enterobacter cloacce and Salmonella species. Chloramphenicol showed lower bactericidal effect than the synthetic compounds. Furthermore, it is apparent that different compounds reacted in different ways against bacteria. Gram (-) bacteria seem to be more sensitive to these compounds than Gram (+) species. An effort was made to correlate the above-mentioned differences in activity with lipophilicity studies. Furthermore, molecular modeling was used to obtain the main conformational features of this class of molecules for future structure-activity relationship studies.
Keywords:
Antibacterial; Antifungal; Conformational properties; Lipophilicity; TriazolesSource:
Bioorganic & Medicinal Chemistry, 2008, 16, 3, 1150-1161
DOI: 10.1016/j.bmc.2007.10.082
ISSN: 0968-0896
PubMed: 18053730