Synthesis, characterization and biological investigations of potentially bioactive heterocyclic compounds containing 4-hydroxy coumarin

Abstract

In this paper, we have reported the synthesis of a series of heterocyclic azo dyes containing 4-hydroxy coumarin by diazo-coupling reaction. The structural aspect of the newly synthesized compounds was accomplished by various physico-chemical techniques like UV-Visible, FT-IR, NMR, and mass spectrometry. The computational calculations and geometrical optimization of the newly synthesized azo dyes were investigated by using Gaussian software with the help of Density functional theory (DFT)/B3LYP method using 6-31G(d,p) basis set at gaseous phase. Also, the quantum chemical parameters were evaluated to understand the structural activity concept of the dyes. The pharmacological efficacy of the azo dyes was investigated by antimicrobial, antitubercular, DNA cleavage and in silico molecular docking studies. All the newly synthesized compounds were able to exhibit significant inhibitory activity against tested microbes. Further, the in silico molecular docking showed effective binding properties of the compounds against RpsA target receptor.

Synthesis and Biological Properties of Coumarin Derivatives. A Review

“…[71] 7-(2-Chloroquinolin-4-yloxy)-4-methyl-2H-chromen-2-ones, Scheme 45, were synthesized by Balaji et al [72] from substituted 1,3-dichloroquinoline and 7-hydroxy-4-methylcoumarin using conventional or under ultrasonic irradiation conditions. Kavetsou et al [73] described the synthesis of new 3-aryl-5substituted-coumarin derivatives in three steps starting from phenylacetic acid and dihydroxyacetophenone, Scheme 46. The corresponding acetoxycoumarin derivatives were reactedwith hydrazine monohydrate in methanol before alkylation with geranylbromide.…”

“…Kavetsou et al [73] . described the synthesis of new 3‐aryl‐5‐substituted‐coumarin derivatives in three steps starting from phenylacetic acid and dihydroxyacetophenone, Scheme 46.…”

(E)-N-(3,4-dimethylisoxazol-5-yl)-4-((4-hydroxy-2-oxo-2H-chromen-3-yl) diazenyl)Benzenesulfonamide; A New Synthetic Anti-Herpetic Agent for HSV-1

“…In previous studies the substitution of aryl or azo group in 4-Hydroxy coumarin moiety has been reported which indicates admirable antimicrobial activities. 9) Some thiazole, pyridine, triazole and phenyl thiazole derivatives of 4-hyroxy coumarin was synthesised by J. Sahoo et al and evaluate their in-vitro antibacterial activities against patogens. 10) A Sabt et al synthesized coumarin-6-sulfonamide derivatives and investigated their anti-proliferative nature and conclude that all synthesized compounds was able to diminish the growth of cancer cell by blocking topoisomerase-2 enzyme while doxorubin used as reference drug.…”

Characterization of the Structure of 2-(4-methyl-2 Phenyl-4, 5-dihydrooxazol-4-ylmethyl)-isoindole-1, 3-dione by 1D, COSY and HSQC 2D NMR Spectroscopy

“…The synthesis of heterocyclic molecules has today become inevitable given its importance in human life. The biological interest [1,2,3] of these molecules is very broad and diversified. Several families of heterocyclic molecules are used as antiviral [4,5], anti tuberculosis [6,7], anti cancer [8,9,10], anti tuberculosis [11,12], anti malaria [13], anti fungus [14].…”