Synthesis of some N-substituted salicylamides structurally related to certain antimicrobials.
The condensation of 5-nitrosalicoylchloride and 5-sulphamoylsalicylic acid with certain amines is described. Reacting the acid chloride with 3-amino-2-oxazolidone, 4-aminophenazone, thiosemicarbazide, 1-aminohydantoin and 2-aminopyridine yielded the correspondong N-substituted 5-nitrosalicylamides (1a-c), while with semicarbazide a disubstituted product type 2 was obtained. On the other hand, when 5-sulphamoylsalicylic acid was condensed with o-chloroaniline, m-chloroaniline and 4-aminophenazone in the presence of phosphorus trichloride, instead of affording the expected condensation products type 3, it yielded N1N5-disubstituted 5-sulphamoylsalicylamides (4a-c). The synthesized compounds were screened for antimicrobial activity.
D000935:Antifungal Agents / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D012457:Salicylamides / Q000138:chemical synthesis* / Q000494:pharmacology
D000935:Antifungal Agents; D007202:Indicators and Reagents; D012457:Salicylamides