Polycyclic ferrocenyl(dihydro)thiazepine derivatives: Diastereo-selective synthesis, characterization, electrochemical behavior, theoretical and biological investigation.

Autor: Sánchez García JJ; Facultad de Química, Universidad Nacional Autónoma de México, CD.MX, 04510, Mexico., Toledano-Magaña Y; Facultad de Química, Universidad Nacional Autónoma de México, CD.MX, 04510, Mexico., Flores-Alamo M; Facultad de Química, Universidad Nacional Autónoma de México, CD.MX, 04510, Mexico., Martínez-Klimova E; Facultad de Química, Universidad Nacional Autónoma de México, CD.MX, 04510, Mexico., Galindo-Murillo R; Department of Medicinal Chemistry, College of Pharmacy, University of Utah, UT 84112, USA., Hernández-Ayala LF; Facultad de Química, Universidad Nacional Autónoma de México, CD.MX, 04510, Mexico., Ortiz-Frade L; Departamento de Electroquímica, Centro de Investigación y Desarrollo Tecnológico en Electroquímica, S.C., Querétaro, 76703, Mexico., García-Ramos JC; Departamento de Fisicoquímica, Instituto de Química, Universidad Nacional Autónoma de México, CD. MX, 04510, Mexico. Electronic address: jcgr@iquimica.unam.mx., Klimova EI; Facultad de Química, Universidad Nacional Autónoma de México, CD.MX, 04510, Mexico. Electronic address: klimova@unam.mx.
Jazyk: angličtina
Zdroj: Journal of inorganic biochemistry [J Inorg Biochem] 2017 Jan; Vol. 166, pp. 141-149. Date of Electronic Publication: 2016 Nov 02.
DOI: 10.1016/j.jinorgbio.2016.09.002
Abstrakt: The reaction of E-2-ferrocenylmethylidenetetralones and E,E-2,6-bis-(ferrocenylmethylidene)-cyclohexanone with 2-aminothiophenol proceed with high diastereoselectivity, forming the ~4.5:1 mixture of trans- and cis-isomers of polycyclic ferrocenylthiazepines, respectively. The reactions of E,E-2,5-bis-(ferrocenylmethylidene)cyclopentanone and E,E-3,5-bis-(ferrocenylmethylidene)-1-methyl-4-piperidone with 2-aminothiophenol take place stereo specifically to form the diastereomeric tricyclic thiazepines of cis- and trans-configuration, respectively. The structures of the obtained compounds were established by IR, 1 H and 13 C NMR spectroscopy and mass-spectrometry. The structures of the trans-tetralino[1,2a]-, trans-5,7-dimethyltetralino[1,2a]-2-ferrocenyl [1,5]benzo-2,3-dihydrothiazepines and cis-5-ferrocenyl-methylidenecyclopentano[1,2a]-2-ferrocenyl- [1,5]benzo-2,3-dihydrothiazepine were confirmed by X-ray diffraction analysis. An electrochemical study reveals that the diferrocenyl derivatives belong to a Class I compounds of the Robin-Day classification. This behavior is explained by the analysis of frontier orbitals as calculated by density functional theory, showing that only one ferrocenyl unit participates in the generation of HOMO and LUMO orbitals. Compounds 4a and 4c showed similar capacity to inhibit the proliferation of HM1: IMSS trophozoite cultures than the first choice drug for human amoebiasis treatment, metronidazole. Morphological changes induced in the trophozoites after drug exposure suggest a redox in balance as the probable mechanism of the parasite death.
(Copyright © 2016 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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