Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides

Abstract

In this work, 15 different coumarin hydrazides were successfully synthesized and screened for their antioxidant and antilipase activities. To do this, firstly, salicylaldehyde derivatives and Meldrum's Acid were reacted in absolute ethanol with catalytic amount of pyridine to obtain coumarin-3-carboxylic acid derivatives (1a-e). Then, these compounds were treated with 1H-benzotriazole in dichloromethane by using thionyl chloride to synthesize benzotriazole derivatives (2a-e). Then, compounds 2a-e were reacted with three commercial hydrazides (nicotinic hydrazide, benzhydrazide,and phenyl acetichydrazide) in ethanol by using microwave irradiation and conventional heating procedures to obtain final products (3-5a-e). Finally, these compounds were tested for their anti-oxidant and anti-lipase activities. The structure of newly synthesized compounds was identified by IR, 1 H NMR, 13 C NMR, and elemental analysis data.

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

“…Yilmaz and Faiz (2018) successfully synthesized 3-(1 H -benzotriazol-1-ylcarbonyl)-2 H -chromen-2-ones 157 from salicyl aldehydes 152 ( Scheme 35 ) [ 102 ]. Coumarin-3-carboxylic acids 154 were obtained from the reaction of salicyl aldehydes 152 and Meldrum’s acid 153 with pyridine as a catalyst.…”

“…The potential antioxidant activity of several coumarin hydrazides was also investigated using the cupric ion reducing antioxidant capacity (CUPRAC) method. All studied compounds reduced cupric ions, and the highest activity was observed for compound 158j , with 1.82 ± 0.08 mg TEAC/mg compound ( Scheme 35 , Figure 3 ) [ 102 ].…”

“…A series of novel coumarin hydrazides were investigated against porcine pancreatic lipase by Yilmaz and Faiz (2018) [ 102 ]. Compound 158n ( Scheme 35 , Figure 11 ) showed the highest activity among the synthesized compounds, with 46.31 ± 3.55% pancreatic lipase inhibition at 10 μM.…”

Design, Synthesis, Molecular Modelling and in Vitro Evaluation of Indolyl Ketohydrazide‐Hydrazone Analogs as Potential Pancreatic Lipase Inhibitors

“…Indole, being a nitrogen containing heterocycle is considered to be a privileged scaffold in drug discovery, owing to its wide range of biological activities [8][9][10] such as antiviral, [11] antiinflammatory, [12] analgesic, [10] anticancer, [13] anti-HIV, [14] antioxidant, [15] antimicrobial [16] and antiobesity. [17,18] Hydrazidehydrazone fragments portray a wide range of pharmacological activity (anticonvulsant, [19] antileishmanial, [20] anticancer, [13] antiobesity, [21] antibacterial, [16] antipsychotic, [22] etc.) and are present in many of the clinically available drugs (Figure 1).…”

Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives

“…Syntheses of some ethyl coumarin-3-carboxylate and other derivatives of coumarin have been described [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Coumarinyl-1,4-benzodioxanes were accessed by the reaction between a variety of 2-[(o-iodophenoxy)methyl]oxiranes and some hydroxycoumarin isomers using CuI and 1,10-phenanthroline as catalysts.…”