Synthesis of coumarin derivatives and investigation of their inhibitory effects on lung cancer cell motility

Abstract

Based on the pharmaceutical potentials of coumarins, which have antitumor activity, we synthesized new coumarin derivatives and evaluated their biological activities. The new coumarin derivatives were chemically synthesized from 4-hydroxycoumarin, and their structures were confirmed by nuclear magnetic resonance data. Ten of the synthesized compounds were investigated for antimetastatic activity against lung carcinoma cells. Several of the tested compounds showed good to mild inhibitory effects on lung cancer cell motility. There were no cytotoxic effects related to the use of these compounds. 4-Hydroxycoumarin derivatives, 4h and 4i, elicited the significant inhibitory effect on lung cancer cell motility by suppressing expression of the epithelial–mesenchymal transition markers N-cadherin, Snail, and Twist.

Recent Trends in the Synthesis and Bioactivity of Coumarin, Coumarin–Chalcone, and Coumarin–Triazole Molecular Hybrids

“…With the same purpose of developing coumarin derivatives, Zhou et al (2022) converted 4-hydroxycoumarin 21 to nitro product 60 ( Scheme 14 ) [ 81 ]. The subsequent reduction of the nitro group gave the amino compound 61 , which underwent substitution with various acid chlorides to form the target compounds 62a – j in good yields.…”

“…The coumarin derivatives tested by Zhou et al (2022) [ 81 ] showed compound 62i ( Scheme 14 , Figure 6 ) to exhibit the best in vitro activity against lung cancer cell motility via an analysis of invasion assay cells treated with 15 μM of the compound. The values of the Relative Invaded Number (RIN) for each lung cancer cell are as follows: A549 = 0.8, H460 = 0.8, H1650 = 0.75, and H1975 = 0.78.…”

“…The amidation of 65 with N-Boc piperazine in the presence of EDC•HCl, HOBt, and DIPEA gave 66. Deprotection of the Boc group using TFA led to the formation of compound 4-hydroxy coumarin 21[81]. The amidation of 65 with N-Boc piperazine in the presence of EDC•HCl, HOBt, and DIPEA gave 66.…”

Comparative studies of immobilized polysaccharide derivatives chiral stationary phases for enantioseparation of furanocoumarins and dihydroflavones and discussion on chiral recognition mechanism

“…Coumarins and flavonoids are two groups of natural products with a great bioactive diversity, widely distributed in plant kingdom [7,8]. They play an important role in anti-oxidation, anti-inflammatory and analgesic, antimicrobial, anti-tumor, anti-virus, and other clinical effects [9][10][11][12]. In addition, it is worth noting that there are one or more chiral centers in the structure of most coumarins and flavonoids, especially furanocoumarins and dihydroflavones, as shown in Figure 1.…”