Preparation, Spectral Characterization and Anticancer Potential of Cinnamic Esters

Gonçalves, Renan O.; Farias,, Iolanda F. de; Silva,, Maria Francilene S.; Pessoa, Cláudia Ó.; Zocolo, Guilherme J.; Zampieri, Davila; Lemos, Telma Leda G. de; Monte, Francisco Jose Q.

doi:10.21577/0103-5053.20210084

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Journal of the Brazilian Chemical Society

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Article • J. Braz. Chem. Soc. 32 (10) • Oct 2021 • https://doi.org/10.21577/0103-5053.20210084 copy

Preparation, Spectral Characterization and Anticancer Potential of Cinnamic Esters

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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%).

Keywords:
cinnamic esters; cytotoxicity; spectral data; Steglich esterification

Compound	IC₅₀ / µM
Compound	HL60	SNB-19	HCT-116	PC3	L929
6	> 89^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	38.3 ± 11.3	23.2 ± 3.5	49.0 ± 5.9	32.5 ± 21.4
8	25.2 ± 3.0	> 88^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 88^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 88^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 88^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;
12	> 84^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	42.1 ± 14.2	16.2 ± 6.3	41.9 ± 7.9	> 84^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;
14	> 80^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 80^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	29.3 ± 7.5	68.1 ± 3.6	> 80^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;
15	79.8 ± 16.4	> 80^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 80^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 80^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 80^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;
18	> 77^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;	> 77	15.38 ± 1.6	67.4 ± 18.1	> 77^a a Inhibition of proliferation did not exceed 50% at the highest concentration tested;
DOX^b b doxorubicin was used as a positive control. IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate; L929: cell murine fibroblast.	0.01 ± 0.009	3.8 ± 0.6	0.35 ± 0.09	1.4 ± 0.3	3.2 ± 0.27

Compound	SI
Compound	HL60	SNB-19	HCT-116	PC3
6	-	0.84	1.4	0.7
8	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.	-	-	-
12	-	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.
14	-	-	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.
15	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.	-	-	-
18	-	-	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.	-^a a Selectivity index could not be calculated in the tested strains because the substances did not present IC50 calculable for the non-tumoral strain (IC50 > 77 µM ). IC50: half maximal inhibitory concentration; HL60: promyelocytic leukemia; SNB-19: astrocytoma, HCT-116: colon carcinoma, human; PC3: prostate.

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