1254358-77-4Relevant academic research and scientific papers
Planarity of benzoylhydrazinedithiocarbazoate tuberculostatics. I. N′-Methyl-substituted 3,4-dichlorobenzoyl monoesters
Szczesio, Malgorzata,Olczak, Andrzej,Gobis, Katarzyna,Foks, Henryk,Glowka, Marek L.
, p. o373-o376 (2012)
Methyl 2-(3,4-dichloro-benzoyl)-1-methylhydrazinecarbodithio-ate, C 10H10Cl2N2OS2, (F1), butyl 2-(3,4-dichlorobenzoyl)-1-methylhydrazinecarbodithio-ate, C 13H16Cl2N2OS2, (F2), and 3,4-dichloro-N-(2-sulfanylidene-1,3-thia-zinan-3-yl)benz-amide, C 11H10Cl2N2OS2, (F3), were studied by X-ray diffraction to test our hypothesis that planarity of aryl - oylhydrazinedithio-carbazic acid esters is a prerequisite for tuberculostatic activity. All compounds examined in this study are inactive and nonplanar due to twists along two specific bonds in the central frame of the molecules. The significant twist at the N - N bond, with an C - N - N - C(S) torsion angle of about 85°, results from repulsion caused by a methyl substituent at the N′ atom of the hydrazide group. The other twist is that within the benzoyl group at the C(O) - Ph bond, i.e. the N - C(=O) - C(phenyl) - C torsion angle: the values found in the studied structures (25-30°) are in agreement with those observed in other compounds containing a similar fragment. As some nonplanar benzoyl derivatives are active, it seems that planarity of the hydrazine-dithio-ate fragment is more important for tuberculostatic activity than planarity of the aryloyl group.
