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- Title
Planarity of benzoyldithiocarbazate tuberculostatics. II. Diesters of benzoyldithiocarbazic acid.
- Authors
Szczesio, Małgorzata; Olczak, Andrzej; Gobis, Katarzyna; Mazerant, Ida; Kałużyńska, Sylwia; Foks, Henryk; Główka, Marek L.
- Abstract
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).
- Subjects
ANTITUBERCULAR agents; DRUG resistance; CRYSTAL structure
- Publication
Acta Crystallographica Section C: Structural Chemistry, 2016, Vol 72, Issue 1, p75
- ISSN
2053-2296
- Publication type
Article
- DOI
10.1107/S2053229615024201