One-pot three-component microwave-assisted synthesis of novel thiazolidinone derivatives containing thieno[d]pyrimidine-4-one moiety as potential antimicrobial agents

Abstract

New 2-methyl-5-(4-oxo-2-(substituted phenyl)thiazolidin-3-yl)thieno[3,4-d]-pyrimidin-4-one, 5-(2,7-diphenyl-5-thioxo-5,6,7,7a-tetrahydrothiazolo[4,5-d]pyrimidin-3(2H)-yl)-2-methylthieno[3,4-d]pyrimidin-4(3H)-one, and 2-methyl-5-(5-phenyl-thiazolo[5,4-d]soxazol-6(5H)-yl)thieno[3,4-d]pyrimidin-4(3H)-one have been prepared under microwave-assisted and conventional conditions. The new compounds were screened for their in vitro antimicrobial activity against two gram-positive bacteria (Bacillus subtilis NCI M-2063 and Staphylococcus aureus NCIM-2901), one gram-negative bacteria (Escherichia coli NCIM-2256), and.three fungal strains (Candida albicans NCIM-3471, Aspergillusfiavus NCIM-539, and Aspergillus niger NCIM-1196) and showed promising biological activity.

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). Likewise, compound 1 was treated with hydrazine hydrate to afford the pyrazolo- [1,2,4]triazole derivatives (4 and 5).…”

“…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). Likewise, compound 1 was treated with hydrazine hydrate to afford the pyrazolo- [1,2,4]triazole derivatives (4 and 5). It is worth to mention that the reaction product is extremely depending on the reaction conditions; refluxing equimolar amounts in AcOH yielded the corresponding N-acetyltriazole derivative 5 in a good yield.…”

“…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.…”

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.…”

Synthesis and Pharmacological Evaluation of Some New Chromeno[3,4‐c]pyrrole‐3,4‐dione‐based N‐Heterocycles as Antimicrobial Agents

“…Consequently, several methods have been reported for preparation of chromene derivatives . Thus, the aforesaid biological significance of chromenes, pyrroles, oxadiazoles, and thiazoles urged us to continue working , aiming at merging of multipharmacophores in single architectures. Herein, we describe the synthesis of 3 as key intermediate graced with a reactive mercaptopyrrole tag.…”