Design, characterization, in vitro antibacterial, antitubercular evaluation and structure–activity relationships of new hydrazinyl thiazolyl coumarin derivatives

Abstract

Herein, we describe the synthesis of 11new thiazolyl coumarin derivatives and evaluation of their potential role as antibacterial and antituberculosis agents. The structures of the synthesized compounds were established by extensive spectroscopic studies (Fourier transform infrared spectroscopy, 1 H-nuclear magnetic resonance, 13 Cnuclear magnetic resonance, 2D-nuclear magnetic resonance and liquid chromatography-mass spectrometry) and elemental analysis.

4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies

“…After 4 h of refluxing, the precipitate was filtered and washed with cold water. Recrystallization from ethanol/ethyl acetate (2:1, v/v) afforded good yields of coumarin thiosemicarbazones ( 5a – 5g ) (Scheme 1 ) [ 19 ].…”

“…Their derivatives are reported to display various biological activities such as as anti-bacterial [ 12 , 13 ], anti-fungal [ 14 – 16 ], anti-coagulant [ 17 ], anti-dengue [ 18 ], anti-tuberculosis [ 19 ], anti-viral [ 20 ], anti-tumor [ 21 , 22 ], anti-HIV [ 23 ] and anti-cytotoxicity [ 24 ]. Impressed by the strong biologically active profile of coumarin derivatives and as a part of our interest in the synthesis and screening of potentially bioactive compounds [ 19 ], we herein, report the synthesis of some novel 4-thiazolidinone coumarin hybrids ( SKYa – SKYg ) to be evaluated for their in vitro anti-bacterial, anti-tubercular activities, and as nonsubstrate based dengue virus NS2B/NS3 serine protease inhibitors via molecular docking approach. We targeted to study the structure–activity-relationship by altering the position of the substituents within the coumarin nucleus, as it is important to recognize the structural features in the coumarin nucleus for the design and development of new coumarin derivatives with remarkable biological activities.…”

Coumarin‐containing hybrids and their antibacterial activities

“…[ 91 ] Dimers 37a,b (MIC: 16–32 µg/ml), which showed equal activity against drug‐sensitive S. aureus and MRSA strains, were more potent than ceftazidime and ceftriaxone (MIC: 32 to >256 µg/ml). [ 92,93 ] The dimers 37 (MIC: 31.2–125 µg/ml) displayed considerable activity against two Gram‐positive bacteria ( S. pneumoniae and S. aureus ) and three Gram‐negative bacteria ( E. coli , E. aerogenes , and S. typhi ), and these two dimers 37a,b (MIC: 31.2–62.5 µg/ml) were not inferior to streptomycin (MIC: 31.2–62.5 µg/ml), kanamycin (MIC: 62.5–125 µg/ml), and vancomycin (MIC: 31.2–250 µg/ml) against all tested organisms.…”

Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures

“…2H-Chromene-2-ones, or coumarins, are a group of natural product found in many plant species belonging to the benzopyrone family. Derivatives, both natural and man-made, have been found to have a wide range of pharmacological activities [1][2][3], including as anti-HIV [4,5], antibacterial [6,7], antifungal [8], anti-inflammatoryl [9], anti-TB [10,11], antileishmanial [12], antimalarial [13], antitumor [14][15][16], and antidepressant activities [17], and act as anticoagulants [18], α-glucosidase inhibitors [19], topoisomerase II inhibitors [20], cholinesterase inhibitors [21], Alzheimer's diseaseinhibitors [22], and antioxidants [23,24]. Coumarins also have applications in cosmetics and can be used as optical brightening agents, laser dyes, and fluorescence markers [25,26] and as liquid crystals [27].…”