Planarity of benzoyldithiocarbazate tuberculostatics. II. Diesters of benzoyldithiocarbazic acid

摘要

The emergence of drug-resistant strains of Mycobacterium tuberculosis has intensified efforts to identify new lead tuberculostatics. Our earlier studies concluded that the planarity of a molecule correlates well with its tuberculostatic activity. According to our hypothesis, only derivatives whose molecules are capable of adopting a planar conformation may show tuberculostatic activity. The structures of three new potentially tuberculostatic compounds, namely N′-[bis(methylsulfanyl)methylidene]-N-methyl-4-nitrobenzohydrazide (denoted G1), C11H13N3O3S2, N′-[bis(benzylsulfanyl)methylidene]-N-methyl-4-nitrobenzohydrazide (denoted G2), C23H21N3O3S2, and N′-[(benzylsulfanyl)(methylsulfanyl)methylidene]-4-nitrobenzohydrazide (denoted G3), C16H15N3O3S2, were determined by X-ray diffraction. The significant distortion from planarity caused by the methyl substituent at the N atom of the hydrazide group or the NO2 substituent in the aromatic ring leads to the loss of tuberculostatic activity for G1, G2 and G4 {systematic name: N′-[bis(methylsulfanyl)methylidene]-2-nitrobenzohydrazide}. A similar effect is observed when there are large substituents at the S atoms (G2 and G3).