Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives

Abstract

A series of novel coumarin-3-carboxamide derivatives were designed and synthesized to evaluate their biological activities. The compounds showed little to no activity against gram-positive and gram-negative bacteria but specifically showed potential to inhibit the growth of cancer cells. In particular, among the tested compounds, 4-fluoro and 2,5-difluoro benzamide derivatives (14b and 14e, respectively) were found to be the most potent derivatives against HepG2 cancer cell lines (IC50 = 2.62–4.85 μM) and HeLa cancer cell lines (IC50 = 0.39–0.75 μM). The activities of these two compounds were comparable to that of the positive control doxorubicin; especially, 4-flurobenzamide derivative (14b) exhibited low cytotoxic activity against LLC-MK2 normal cell lines, with IC50 more than 100 μM. The molecular docking study of the synthesized compounds revealed the binding to the active site of the CK2 enzyme, indicating that the presence of the benzamide functionality is an important feature for anticancer activity.

Bioactivity of Chitosan-Based Particles Loaded with Plant-Derived Extracts for Biomedical Applications: Emphasis on Antimicrobial Fiber-Based Systems

“…Their chemical versatility has additionally enabled the synthesis of a large variety of functionalized skeletons. Modes of action are variable, yet potent [77][78][79][80]. Inhibition of cell wall synthesis, permeabilization and disintegration of bacterial peripheral layers, restriction of bacterial physiology, oxygen uptake and oxidative phosphorylation, efflux pump inhibition, modulation of antibiotic susceptibility, biofilm inhibition, hindrance of the microbial protein adhesion to the host's polysaccharide receptors, and attenuation of bacterial virulence, are known and acclaimed mechanisms of action of such elements [67,69,70,81].…”

Investigation of Novel Mucorales Fungal Inhibitors: Synthesis, In‐Silico Study and Anti‐Fungal Potency of Novel Class of Coumarin‐6‐Sulfonamides‐Thiazole and Thiadiazole Hybrids

“…In ddition to, their potent activity against human fungal pathogens such as C. tropicalis, C. albicans, and Aspergillus fumigatus. [18][19][20] Over the past few years, compounds containing thiazole and/or thiadiazole scaffold are attractive to medicinal chemistry due to their unique chemical properties and diversity of the biological activities. [20][21][22][23][24][25] Therefore, they have therapeutic effects against several diseases such as antimalarial, antimicrobial, antiproliferative agents and anti-inflammatory [26][27][28][29][30] besides their significant with various fungicidal activities .…”

“…[18][19][20] Over the past few years, compounds containing thiazole and/or thiadiazole scaffold are attractive to medicinal chemistry due to their unique chemical properties and diversity of the biological activities. [20][21][22][23][24][25] Therefore, they have therapeutic effects against several diseases such as antimalarial, antimicrobial, antiproliferative agents and anti-inflammatory [26][27][28][29][30] besides their significant with various fungicidal activities . [31,32] In addition, many scientific reported have also demonstrated that the sulfonamide moiety itself possess interesting pharmacological activities and therapeutic functions.…”

“…The great attention paid by researchers to the study of coumarin derivatives is explained by their broad spectrum of biological activities including anti‐inflammatory, [17] antidiabetic, antiAlzheimer, anticancer, antioxidant, Anticonvulscent, antituberculosis, and as inhibitors of SARS‐CoV‐2 (COVID‐19) virus. In ddition to, their potent activity against human fungal pathogens such as C. tropicalis, C. albicans, and Aspergillus fumigatus [18–20] …”

Coumarin and Its Derivatives—Editorial

“…Anticancer activities for coumarins have been also reported. Coumarin-3-carboxamide derivatives have been reported, and 4-fluoro and 2,5-difluoro benzamides presented activities against HepG2 and HeLa cancer cell lines comparable to doxorubicin, exhibiting low cytotoxicity against LLC-MK2 normal cell line [12]. From the combination of simple coumarins (osthole, umbelliferone, esculin or 4-hydroxycoumarin) with sorafenib, an antiglioma compound was also reported by studying human glioblastoma multiforme (T98G) and anaplastic astrocytoma (MOGGCCM) cells lines [13].…”