Title:	Preparation, spectral characterization and anticancer potential of cinnamic esters.
Authors:	GONÇALVES, R. O. FARIAS, I. F. de SILVA, M. F. S. PESSOA, C. Ó. ZOCOLO, G. J. ZAMPIERI, D. LEMOS, T. L. G. de MONTE, F. J. Q.
Affiliation:	RENAN O. GONÇALVES, UNIVERSIDADE FEDERAL DO CEARÁ IOLANDA F. DE FARIAS, UNIVERSIDADE FEDERAL DO CEARÁ MARIA FRANCILENE S. SILVA, UNIVERSIDADE FEDERAL DO CEARÁ CLÁUDIA Ó. PESSOA, UNIVERSIDADE FEDERAL DO CEARÁ GUILHERME JULIAO ZOCOLO, CNPAT DAVILA ZAMPIERI, UNIVERSIDADE FEDERAL DO CEARÁ TELMA LEDA G. DE LEMOS, UNIVERSIDADE FEDERAL DO CEARÁ FRANCISCO JOSE Q. MONTE, UNIVERSIDADE FEDERAL DO CEARÁ.
Date Issued:	2021
Citation:	Journal of the Brazilian Chemical Society, v. 32, n. 10, p. 1931-1942, 2021.
Description:	Cinnamic acid and its derivatives show a remarkable variety of biological activities and are often studied in search of the development of new and highly effective drugs. This work aims to synthesize, characterize and evaluate the cytotoxic activity of esters derived from cinnamic acid. Eighteen esters were synthesized through Steglich’s esterification, of which eleven were not reported in the literature. All compounds were fully characterized by Fourier transform infrared epectroscopy (FTIR), nuclear magnetic resonance (1H and 13C NMR) and high-resolution mass spectrometry (HRMS) data. The cytotoxic activity of esters obtained was evaluated using four human tumor cell lines: SNB-19 (astrocytoma), HCT-116 (colon carcinoma, human), PC3 (prostate) and HL60 (promyelocytic leukemia) through the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium (MTT) colorimetric assay. These studies showed that the compound 3-methoxybenzyl (E)-3-(4-methoxyphenyl)acrylate (12) is the most potent against HCT-116, PC3 and SBN-19 cells, with the lowest half maximal inhibitory concentration (IC50) value of 16.2 µM in the HCT-116 strain. The derivatives were obtained in good yields (76.6-95%), except for compounds 5-isopropyl-2-methylphenyl (E)-3-(3-hydroxy-4-methoxyphenyl)acrylate (17) (18.6%) and 2-isopropyl-5-methylphenyl (E)-3-(3-hydroxy-4-methoxyphenyl)acrylate (18) (15.5%).
NAL Thesaurus:	Cytotoxicity
Keywords:	Cinnamic esters Spectral data Steglich esterification Ésteres cinâmicos Citotoxicidade Dados espectrais Esterificação de Steglich
ISSN:	1678-4790
DOI:	https://doi.org/10.21577/0103-5053.20210084
Type of Material:	Artigo de periódico
Access:	openAccess
Appears in Collections:	Artigo em periódico indexado (CNPAT)