Microwave-Assisted Synthesis of Novel 2H-Chromene Derivatives Bearing Phenylthiazolidinones and Their Biological Activity Assessment

Abstract

6-Hydroxy-2-oxo-2H-chromene-4-carbaldehyde (2), 6-chloro-2-oxo-2H-chromene-4-carbaldehyde (3) and 6-hydrazinyl-4-methyl-2H-chromen-2-one (5) were prepared as single-pharmacophore motif key intermediates. Compounds 2, 3 and 5 were incorporated in a series of multicomponent reactions (MCRs), under microwave assistance as well as conventional chemical synthesis processes, to afford a series of three and/or four-pharmacophoric-motif conjugates 8a,b, 11, 13, 16, 17, 19 and 20 in good yields. The newly synthesized compounds were characterized by IR, NMR, 13 C-NMR, MS and elemental analyses. Finally the synthesized compounds have been screened for their biological activity whereupon they exhibited remarkable antimicrobial activity on different classes of bacteria and the fungus.

Pyrazole‐1‐carbothioamide as a Potent Precursor for Synthesis of Some New N‐heterocycles of Potential Biological Activity

“…In the present work and as a part of our incessant efforts [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] for the synthesis of N-heterocycles, we report the efficient synthesis of new annelated pyrazole, triazole, and thiazole analogs as bio-functional conjugates, employing the easily obtainable N-acetyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (1) [41] as a precursor. The reactivity of the N-acetylcarbothioamide tagged intermediate 1 towards some nitrogen nucleophiles was scrutinized; thus, compound 1 was cyclocondensed with semicarbazide and/or thiosemicarbazide in refluxing EtOH containing catalytic amount of HCl to afford the pyrazolo- [1,2,4]triazole analogs (2 and 3) in a moderate yield (Scheme 1).…”

“…In continuation of our research program [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15], we are aiming to merge chemical architectures of considerable pharmacophoric impacts for improving their therapeutic potentials, in particular against profound diseases. Thus, we initiated a program aiming at merging pyrazole, thiazole, and 1,2,4-triazole moieties in single architecture.…”

Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

“…[20] The advantage of multicomponent reactions (MCRs) in the synthesis of drug-like compounds is clear due to their ability to prove a wide range of chemical-structure diversity in the products with high atom economy. [28,29] Recently, α-aminophosphonates are a major class of compounds in modern medicinal chemistry due to their pharmacological activities, [30] as antitumor agents, [31,32] enzyme inhibitors, [33] antibacterial agents, [34] and herbicides. The condensation of aldehydes and amines via classical MCRs gives reactive imine derivatives.…”

Convenient Synthesis of Novel Nitrogen Bridgehead Heterocycles Utilizing 3‐Mercapto‐6H‐[1,2,4,5]oxatriazino[3,2‐a]isoindol‐6‐one as a New Synthon

“…Figure shows some of the reported biologically active isoindole, azine, and azole analogs. Thus, the aforesaid biological significance of these moieties compelled us to continue working on the synthesis and screening of new heterocyclic compounds containing N ‐heterocyclic systems resulting in more potent compounds.…”