Synthesis and biological activity of some new 3,6-dinitro-1:8-naphthaloyl- and 3,6-diamino-1:8-naphthaloylamino acids and dipeptide derivatives.
Synthesis of a series of 3,6-dinitro-1:8-naphthaloylamino acids (II-IX) and some of their corresponding methyl esters (X-XVI) and 3,6-diamino-1:8-naphthaloylamino acid derivatives (XXIX-XXXVI) is described. Coupling of 3,6-dinitro-1:8-naphthaloylamino acids with amino acid methyl ester hydrochlorides in dioxane-DMF-Et3N medium using DCC method furnishes the desired 3,6-dinitro-1:8-naphthaloyldipeptide methyl esters (XVII-XXVIII). Most of the synthesized 3,6-dinitro-1:8-naphthaloylamino acids, esters and dipeptide derivatives (compounds III-VI, XI-XV, XVII, XIX-XXI, XXIII and XXV) and 3,6-diamino-1:8-naphthaloylamino acid derivatives (XXIX-XXXV) were found to be active against a number of microorganisms.
D000596:Amino Acids / Q000494:pharmacology*; D000900:Anti-Bacterial Agents; D001407:Bacillus / Q000187:drug effects; D001409:Bacillus cereus / Q000187:drug effects; D001412:Bacillus subtilis / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D008722:Methods; D009281:Naphthalenes; D010408:Penicillium chrysogenum / Q000187:drug effects; D012485:Salmonella typhi / Q000187:drug effects; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D004151:Dipeptides; D009281:Naphthalenes