Synthesis, Anti–HIV, and Antifungal Activity of New Benzensulfonamides Bearing the 2,5-Disubstituted-1,3,4-Oxadiazole Moiety

Abstract

A series of novel chiral and achiral N-[1-(1,3,4-oxadiazol-2ylthio)alkyl]-4-methyl/chloro/methoxybenzenesulfonamides 5a–l were prepared by the reaction of 4-(4-methyl, chloro, methoxyphenylsulfonamido)alkyl carboxylic acid hydrazides 4a–l with CS₂ and KOH. Another series of new secondary benzenesulfonamides 10a–j and bis-benzenesulfonamides 11a–j have been synthesized by a new approach using Et₃N and dimethylaminopyridine. All synthesized compounds were characterized by physical, microanalytical, and spectral data. Some of the synthesized compounds were screened in vitro for their anti–HIV and antifungal activities.

Keywords:

• Antifungal activity
• anti–HIV activity
• benezenesulfonamides chiral sulfonamides
• 1,3,4-oxadiazole

Notes

^a Anti–HIV-1 activity measured with strain III_B.

^b Anti–HIV-2 activity measured with strain ROD.

^c Compound concentration required to reduce the viability of mock-infected MT-4 cells by 50%.

^d Compound concentration required to achieve 50% protection of MT-4 cells from HIV-1 and 2 induced cytopathogenicity.

^e SI: Selectivity index (IC₅₀/CC₅₀).