Phenethyl p-coumarate and N-phenethyl-p-coumaramide: Synthesis, Characterization, Docking Studies, and Anticancer Activity through P388 Cell

Abstract

Most p-coumaric acid derivatives and molecules containing phenethyl moiety have a potential in anticancer activity. Thus, combining a p-coumaroyl group and a phenethyl moiety in one compound will increase anticancer activity. The principal objective of this research was to incorporate p-coumaroyl and phenethyl moieties to form an ester, phenethyl p-coumarate (5), and an amide, N-phenethyl-p-coumaramide (6), then tested their anticancer activity using P388 leukemia murine cells. The characterization by FTIR method, compound 5 gave a strong absorption band of alkyl C-O bond that appears at 1165,00 cm-1, and compound 6 gave a sharp and medium absorption band of N-H bond that appears at 3396.64 cm-1. Docking studies of both compounds showed a hydrogen bond with Ile839 residue, and an additional hydrogen bond appeared between compound 6 and Ser991 residue. Based on their activity against P388 leukemia murine cells, these compounds are more active than their analog compounds of N-feruloylpiperidine and N-feruloylmorpholine, which have been synthesized previously. Compounds 5 and 6 have a high potential to be used as anticancer drugs.

Synthesis of <i>N</i>-phenethyl-<i>p</i>-methoxycinnamamide and <i>N</i>-morpholinyl-<i>p</i>-methoxycinnamamide, <i>In Vitro</i> and <i>In Silico</i> Study as α-Glucosidase Inhibitor

“…The two most abundant compounds in the aromatic ginger essential oil were trans-ethyl-pmethoxycinnamate and trans-ethyl cinnamate [1][2]5]. Ethyl-p-methoxycinnamate and its derivatives had many benefits, including as anticancer [6][7][8], anti-inflammatory [9][10], anti-tuberculosis [11], anti-neoplastic [12], antimicrobe [13], and antidiabetic [14] agents. The study of K. galanga L. extract as an antidiabetic using the Gavage method every day for one month found that diabetic rats before and after treatment with K. galanga L. extract showed a significant difference in reducing the amount of blood glucose [15].…”