Synthesis of omega-(4-aminophenylsulfonamido)alkyl disulfides and thiosulfates and their activity against dihydropteroate synthetase from sulfanilamide-resistant Neisseria gonorrhoeae.
A series of omega-(4-aminophenylsulfonamido)alkyl disulfides and omega-(4-aminophenylsulfonamido)alkanethiosulfates was synthesized from the reaction of p-acetamidobenzenesulfanilyl chloride and either the aminoalkyl disulfide dihydrobromide or the aminoalkyl bromide hydrobromide followed by sodium thiosulfate. Several of the compounds showed inhibitory activity against dihydropteroate synthetase isolated from a sulfanilamide-resistant strain of Neisseria gonorrhoeae of the same order of activity as that of sulfanilamide. An increase in the hydrophobic nature of the sulfanilamide structure did not increase inhibitory activity against this enzyme.
D055598:Chemical Phenomena; D002621:Chemistry; D002627:Chemistry, Physical; D004094:Dihydropteroate Synthase / Q000037:antagonists & inhibitors*; D004220:Disulfides / Q000138:chemical synthesis / Q000494:pharmacology; D004352:Drug Resistance, Microbial; D009344:Neisseria gonorrhoeae / Q000187:drug effects* / Q000201:enzymology; D013424:Sulfanilamides / Q000494:pharmacology*; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology; D013885:Thiosulfates / Q000138:chemical synthesis / Q000494:pharmacology; D014166:Transferases / Q000037:antagonists & inhibitors*
D004220:Disulfides; D013424:Sulfanilamides; D013449:Sulfonamides; D013885:Thiosulfates; D014166:Transferases; D004094:Dihydropteroate Synthase