A study of antituberculosis activities and crystal structures of (E)-2-[2-(arylidene)hydrazinyl]pyrimidine and (E)-N ¹-(arylidene)pyrimidine-2-carbohydrazide derivatives

Abstract A study of the anti-tuberculosis activity against Mycobacterium tuberculosis ATTC 27294 and an X-ray structural determination of (E)-2-[2-(arylidene)hydrazinyl]pyrimidine, 1, and (E)-N 1-(arylidene)pyrimidine-2-carbohydazide, 2, derivatives are presented. The effect of the substituents in the aryl moiety on the antituberculosis (anti-TB) activities of 1 and 2 is compared with that of other heteroaryl hydrazonyl and acylhydrazonyl derivatives. The biological activities of 1 do not depend on the coordinating ability of the substituted aryl group: in 2, the most effective aryl group is 5-nitrofuranyl. The structure determinations of (E)-2-((2-(pyrimidin-2-yl)hydrazono)methyl)-phenol, (E)-N′-(2,5-dihydroxybenzylidene)pyrimidine-2-carbohydrazide and of the hydrate of (E)-N′-(2-hydroxy-4-methylbenzylidene)pyrimidine-2-carbohydrazide, and a literature search of related structures in the CCDC data base, allowed an examination of the more important interactions, including the occurrence of X–Y⋯π interactions.