Open AccessPhenethyl p-coumarate and N-phenethyl-p-coumaramide: Synthesis, Characterization, Docking Studies, and Anticancer Activity through P388 Cell
Author(s) -
Firdaus Firdaus,
Nunuk Hariani Soekamto,
Seniwati Seniwati,
Syadza Firdausiah,
Herlina Rasyid,
Bahja Bahja,
Muhammad Fajar Islam
Publication year - 2022
Publication title -
sains malaysiana
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.251
H-Index - 29
eISSN - 2735-0118
pISSN - 0126-6039
DOI - 10.17576/jsm-2022-5104-11
Subject(s) - chemistry , moiety , docking (animal) , stereochemistry , amide , hydrogen bond , residue (chemistry) , benzamide , carboxamide , molecule , biochemistry , organic chemistry , medicine , nursing
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.