Hirshfeld analysis and mol-ecular docking with the RDR enzyme of 2-(5-chloro-2-oxoindolin-3-yl-idene)-N-methyl-hydrazinecarbo-thio-amide.

ABSTRACT: The acetic acid-catalyzed reaction between 5-chloro-isatin and 4-methyl-thio-semicarbazide yields the title compound, C10H9ClN4OS (I) (common name: 5-chloro-isatin-4-methyl-thio-semicarbazone). The mol-ecule is nearly planar (r.m.s. deviation = 0.047?Å for all non-H atoms), with a maximum deviation of 0.089?(1)?Å for the O atom. An S(6) ring motif formed by an intra-molecular N-H?O hydrogen bond is observed. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by N-H?S hydrogen bonds, forming a three-dimensional supra-molecular structure. The three-dimensional framework is reinforced by C-H?? inter-actions. The absolute structure of the mol-ecule in the crystal was determined by resonant scattering [Flack parameter = 0.006?(9)]. The crystal structure of the same compound, measured at 100?K, has been reported on previously [Qasem Ali et al. (2012 ?). Acta Cryst. E68, o964-o965]. The Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H?H (23.1%), H?C (18.4%), H?Cl (13.7%), H?S (12.0%) and H?O (11.3%) inter-actions. A mol-ecular docking evaluation of the title compound with the ribonucleoside diphosphate reductase (RDR) enzyme was carried out. The title compound (I) and the active site of the selected enzyme show Cl?H-C(LYS140), Cg(aromatic ring)?H-C(SER71), H?O-C(GLU200) and FeIII?O?FeIII inter-molecular inter-actions, which suggests a solid theoretical structure-activity relationship.

SUBMITTER: Velasques JM 

PROVIDER: S-EPMC5418788 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature