Synthesis and Biological Evaluations of N-(4-Substituted Phenyl)-7-Hydroxy-4-Methyl-2-Oxoquinoline-1(2H)-Carbothioamides

Abstract

The chemicals were purchased from CDH, Merck and Spectrochem (India). The melting point was recorded through open capillary method and was uncorrected. The progress or reaction was monitored by thin layer chromatography (TLC Silica gel 60 F254) and benzene/methanol (8:2) was used as eluent. The spots were visualized under iodine vapors or UV light. IR spectra were recorded on a Bruker Alpha II FT-IR spectrometer, while the nuclear magnetic resonance spectra were recorded on a Bruker AvIII HD-300 ( 1 H NMR at 300 MHz and 13 C NMR at 75 MHz) in DMSO-d6. The mass spectra were recorded on a Waters ACQUITY® TQD LCMS using ESI. General method for the synthesis of N-(4-substituted phenyl)-7-hydroxy-4-methyl-2oxoquinoline-1(2H)-carbothioamides (5a-g)An equimolar amount of 7-hydroxy-4-methyl coumarin (3) (1mmol; 176 mg) and substituted phenyl thiourea (4a-g) (1 mmol) was fused together at 200 ºC on oil bath for 1 h. The reaction mixture was then cooled and 5 mL ethanol was added followed by addition of 5 mL water. The separated solid was collected by vacuum filtration, washed with water, dried and re-crystallizes from acetic acid. N-(4-Chlorophenyl)-7-hydroxy-4-methyl-2-oxoquinoline-1(2H)-carbothioamide (5a) IR 3406

QSAR Studies, Molecular Docking, Molecular Dynamics, Synthesis, and Biological Evaluation of Novel Quinolinone-Based Thiosemicarbazones against Mycobacterium tuberculosis

“…Antibiotic resistance requires a different treatment with second-generation therapeutics [8]. Unfortunately, new TB strains develop resistance to first and second generation [9]. As a result, morbidity and mortality are higher in immunosuppressed HIV patients [10].…”

“…For example, hybrids such as quinoline-thiosemicarbazones 8 [31], benzaldehyde thiosemicar-bazones 9 [32], and thiosemicarbazones 10 [33] have been reported as excellent inhibitors of M. tuberculosis. In addition, different possible tuberculosis protein targets were reported for these structures, representing a real opportunity to design new compounds with other mechanisms of action, which are a cornerstone to fight against tuberculosis resistance to the current antibiotics [9,[34][35][36][37][38][39][40].…”

Green Synthesis of Oxoquinoline-1(2H)-Carboxamide as Antiproliferative and Antioxidant Agents: An Experimental and In-Silico Approach to High Altitude Related Disorders

“… * Benzen: acetone (9:1); a Yield of final dried compounds; b Reaction condition: 7-hydroxy-4-methyl-2 H -chromen-2-one ( 3 ) (1 mmol; 176 mg) and substituted phenyl urea ( 4a – j ) (1 mmol); 200 °C (fusion) [ 41 ]; c Reaction condition: 7-hydroxy-4-methyl-2 H -chromen-2-one ( 3 ) (1 mmol; 176 mg) and substituted phenyl urea ( 4a – j ) (1 mmol); H 2 O 10 mL; ))))) (Ultrasound) 20 KHz; 130 W. …”