Synthesis of selected 5-thio-substituted tetrazole derivatives and evaluation of their antibacterial and antifungal activities

Abstract

Several 5-thio-substituted tetrazole derivatives were efficiently synthesized by a three-step process. The substituted tetrazol-5-thiol, namely, 1-benzyl-1H-tetrazol-5-thiol (2) was prepared by refluxing commercially available benzyl isothiocyanate (1) with sodium azide in water. The second step was the synthesis of 1-benzyl-5-[(3-bromopropyl) thio]tetrazole (3) by thio alkylation of tetrazol-5-thiol (2) with 1,3- dibromopropane in tetrahydrofuran. Finally, the 5-thio-substituted tetrazole derivatives 4a-i were prepared by condensation of (3) with the corresponding amine or thiol. The structures of the newly synthesized compounds were characterized by NMR, LC/MS/MS, IR spectral data and elemental analysis. All the synthesized compounds were screened for their antibacterial and antifungal activities.

N-[3-Methyl-1-phenyl-1-(1H-tetrazol-1-yl)butan-2-yl]acetamide

“…Tetrazoles are reported to exhibits antihypertensive (Sharma et al, 2010), antimicrobial (Yildirir et al, 2009), antibacterial, antifungal (Dhayanithi et al, 2011) and anticancer activities (Bhaskar & Mohite, 2010). These functional units exhibit strong networking ability as ligands.…”

Design, synthesis, and evaluations of antifungal activity of novel phenyl(2H-tetrazol-5-yl)methanamine derivatives

“…General procedure for synthesis of phenyl(2H -tetrazol-5-yl) methanamine derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) To a mixture of α-amino nitrile (1.00 mol), sodium azide (1.05 mol), and zinc chloride (0.50 mol), isopropyl alcohol was refluxed for 16 h. The progress of the reaction was Compd.…”

“…The in vitro minimal inhibitory concentrations (MICs) of the target compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were determined by the disk diffusion method according to the methods defined by the National Committee for Clinical Laboratory Standards [21]. The MIC was defined as the lowest concentration that showed no growth.…”

“…The hydrophobic group is required for activity, so for increasing hydrophobicity of the compound, phenyl ring is replaced by triazole moiety [13,14]. Tetrazole substituent shows antifungal activity so we have replaced one triazole ring of fluconazole by tetrazole ring.…”

“…Tetrazole substituent shows antifungal activity so we have replaced one triazole ring of fluconazole by tetrazole ring. An attempt is made for substitution of -CH 3 near tetrazole which improves the spectrum of activity [13].…”