Synthesis and Antibacterial Activity of Sulfanilamides Containing Sterically Hindered Phenol Fragments

Abstract

Abstract: New sulfanilamide derivatives containing sterically hindered phenol fragments have been synthesized via modification of the amino group by reaction with 3,5-di-tert-butyl-4-hydroxybenzyl acetate and diazotization followed by diazo coupling with 2,4-di-tert-butylphenol. 4-Aminobenzenesulfonamide derivatives at the sulfonamide group have been obtained by converting acetyl-protected 4-aminobenzenesulfonyl chloride to the corresponding sulfonohydrazide and reacting the latter with 3,5-di-tert-butyl-4-hydroxybenzyl acetate, sterically hindered hydroxybenzaldehydes, and N-(3,5-di-tert-butyl-4-hydroxybenzyl)isatin. Modification of sulfanilamide with sterically hindered phenol fragments significantly increased antibacterial activity.