Synthesis, antiproliferative activities, and DNA binding of coumarin‐3‐formamido derivatives

Abstract

Ten coumarin‐3‐formamido derivatives, N‐benzyl‐coumarin‐3‐carboxamide (2), N‐fluorobenzyl‐coumarin‐3‐carboxamide (3–5), N‐methoxybenzyl‐coumarin‐3‐carboxamide (6–8), N‐((1‐methyl‐1H‐imidazol‐5‐yl)methyl)‐coumarin‐3‐carboxamide (9), N‐(thiophen‐2‐ylmethyl)‐coumarin‐3‐carboxamide (10), and N‐(furan‐2‐ylmethyl)‐coumarin‐3‐carboxamide (11), were synthesized and characterized. Compound 5 crystallizes in a monoclinic system P21/c space group with four chemical formulas in a unit cell; molecules of compound 5 are self‐assembled into a two‐dimensional supramolecular structure by intermolecular hydrogen bonds and C⋯C π stacking. The potential anticancer effects of these compounds on HeLa (cervical carcinoma), MCF‐7 (breast), A549 (lung), HepG2 (liver), and human umbilical vein (HUVEC) cells were examined. Compared with compounds 1–8 and 10–11, compound 9 exhibits potent in vitro cytotoxicity against HeLa cells and lower cytotoxicity against normal cells. Therefore, further in‐depth investigations of compound 9 were performed. Absorption titration experiments and fluorescence spectroscopy studies suggested that compound 9 binds to DNA through the intercalation mode.

Fragment‐type 4‐azolylcoumarin derivatives with anticancer properties

“…Anticancer properties of various coumarin derivatives were comprehensively examined and it is clear that they can inhibit the growth, proliferation, and metastasis of cancer cells (Figure 1). [ 18–30 ]…”

Piperidine-Iodine as Efficient Dual Catalyst for the One-Pot, Three-Component Synthesis of Coumarin-3-Carboxamides

“…If necessary, further purification was performed by recrystallization from ethanol. The identity of the known products was confirmed by a comparison of their spectroscopic data and physical properties [ 20 , 24 , 40 , 41 , 42 , 43 , 44 , 45 , 46 ]. The characterization data of synthesized compounds are given in the Supplementary Materials .…”

Synthesis and antimicrobially activities of coumarin-3-carboxamide derivatives

“…1,2 Studies in the literature show that the activities vary according to the type and binding site of the attached substituent. The activities of coumarin 3carboxamide compounds have been found in the literature as antitumor, [3][4][5][6][7][8][9][10][11] anti-inflammatory, 12,13 anti-Alzheimer, [14][15][16][17] anti-coagulant, anti-Helicobacter pyroli agent, [19][20][21] and antimicrobial. 9,[22][23][24][25] Carbendazim, which is a carboxylic acid amide, is one of the first fungicides to be mentioned in the literature as an excellent fungicide since the 1960s.…”