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Complete chemical shift assignment and molecular modeling studies of two chromene derivatives as potential leads for new anticancer drugs.
Rubim de Santana, Priscila Ivo; Ferreira Neto, Denise Cristian; Goncalves, Arlan da Silva; Almeida, Joyce Sobreiro Francisco Diz de; França, Tanos Celmar Costa; Figueroa-Villar, José Daniel.
Afiliação
  • Rubim de Santana PI; Medicinal Chemistry Group, Chemical Engineering Department, Military Institute of Engineering, Rio de Janeiro, Brazil.
  • Ferreira Neto DC; Medicinal Chemistry Group, Chemical Engineering Department, Military Institute of Engineering, Rio de Janeiro, Brazil.
  • Goncalves ADS; Laboratory of Molecular Modeling Applied to the Chemical and Biological Defense (LMCBD), Military Institute of Engineering, Rio de Janeiro, Brazil.
  • Almeida JSFD; Department of Chemistry, Faculty of Science, University of Hradec Kralove, Hradec Kralove, Czech Republic.
  • França TCC; Laboratory of Molecular Modeling Applied to the Chemical and Biological Defense (LMCBD), Military Institute of Engineering, Rio de Janeiro, Brazil.
  • Figueroa-Villar JD; Laboratory of Molecular Modeling Applied to the Chemical and Biological Defense (LMCBD), Military Institute of Engineering, Rio de Janeiro, Brazil.
J Biomol Struct Dyn ; 39(15): 5498-5508, 2021 09.
Article em En | MEDLINE | ID: mdl-32657645
The compounds 7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one (5) and 5-[-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione (7), were synthesized from dimedone and barbituric acid and had their three-dimensional structures and precise chemical shifts assignments obtained by Nuclear Magnetic Resonance (NMR) from 1H, 13C, APT, COSY, HSQC, and HMBC spectra. Additional HOMO-LUMO DFT calculations corroborated the NMR results and pointed to the most stable stereoisomers of each compound. Besides, further docking and molecular dynamic studies suggest that the stereoisomers (9S)-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one, and 5-[(5S)-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione of these compounds may act as DNA intercalators and qualify as potential leads for the development of new anticancer drugs.Communicated by Ramaswamy H. Sarma.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Benzopiranos / Antineoplásicos Idioma: En Revista: J Biomol Struct Dyn Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Brasil País de publicação: Reino Unido
Texto completo
Adicionar na Minha BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Benzopiranos / Antineoplásicos Idioma: En Revista: J Biomol Struct Dyn Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Brasil País de publicação: Reino Unido