Hirshfeld analysis and molecular docking with the RDR enzyme of 2-(5-chloro-2-oxoindolin-3-ylidene)-N-methylhydrazinecarbothioamide

Registro completo de metadados
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.creatorVelasques, Jecika Maciel-
Autor(es): dc.creatorGervini, Vanessa Carratu-
Autor(es): dc.creatorKickofel, Lisliane-
Autor(es): dc.creatorDe Farias, Renan Lira-
Autor(es): dc.creatorDe Oliveira, Adriano Bof-
Data de aceite: dc.date.accessioned2021-03-11T00:32:32Z-
Data de disponibilização: dc.date.available2021-03-11T00:32:32Z-
Data de envio: dc.date.issued2018-12-11-
Data de envio: dc.date.issued2018-12-11-
Data de envio: dc.date.issued2017-01-01-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1107/S2056989017005461-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/169709-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/169709-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionProcesso FAPESP: 2015/12098-0-
Descrição: dc.descriptionThe acetic acid-catalyzed reaction between 5-chloroisatin and 4-methylthiosemicarbazide yields the title compound, C10H9ClN4OS (I) (common name: 5-chloroisatin-4-methylthiosemicarbazone). The molecule is nearly planar (r.m.s. deviation = 0.047Å 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 intramolecular N - H⋯O hydrogen bond is observed. In the crystal, molecules 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 supramolecular structure. The three-dimensional framework is reinforced by C - H⋯π interactions. The absolute structure of the molecule in the crystal was determined by resonant scattering [Flack parameter = 0.006(9)]. The crystal structure of the same compound, measured at 100K, 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%) interactions. A molecular 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 intermolecular interactions, which suggests a solid theoretical structure-activity relationship.-
Formato: dc.format702-707-
Idioma: dc.languageen-
Relação: dc.relationActa Crystallographica Section E: Crystallographic Communications-
Relação: dc.relation0,153-
Direitos: dc.rightsopenAccess-
Palavras-chave: dc.subjectcrystal structure-
Palavras-chave: dc.subjectHirshfeld surface analysis-
Palavras-chave: dc.subjecthydrogen bonding-
Palavras-chave: dc.subjectisatin thiosemicarbazone derivative-
Palavras-chave: dc.subjectRDR-thiosemicarbazone in silico evaluation-
Título: dc.titleHirshfeld analysis and molecular docking with the RDR enzyme of 2-(5-chloro-2-oxoindolin-3-ylidene)-N-methylhydrazinecarbothioamide-
Tipo de arquivo: dc.typelivro digital-
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