title: Planarity of benzoylhydrazine-dithiocarbazoate tuberculostatics. I. N'-Methyl-substituted 3,4-dichlorobenzoyl monoesters.
abstract: Methyl 2-(3,4-dichlorobenzoyl)-1-methylhydrazinecarbodithioate, C(10)H(10)Cl(2)N(2)OS(2), (F1), butyl 2-(3,4-dichlorobenzoyl)-1-methylhydrazinecarbodithioate, C(13)H(16)Cl(2)N(2)OS(2), (F2), and 3,4-dichloro-N-(2-sulfanylidene-1,3-thiazinan-3-yl)benzamide, C(11)H(10)Cl(2)N(2)OS(2), (F3), were studied by X-ray diffraction to test our hypothesis that planarity of aryloylhydrazinedithiocarbazic 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 hydrazinedithioate fragment is more important for tuberculostatic activity than planarity of the aryloyl group.
authors.affiliation: Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Szczesio
authors.forename: Andrzej
authors.initials: A
authors.lastname: Olczak
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Gobis
authors.forename: Henryk
authors.initials: H
authors.lastname: Foks
authors.forename: Marek L
authors.initials: ML
authors.lastname: Główka