Synthesis and Antitumor/Antiviral Evaluation of 6–Thienyl–5–cyano-2–thiouracil Derivatives and Their Thiogalactosides Analogs

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).…”

“…The carbothioamide derivative 3 was incorporated in a set of manipulations aiming at exploiting the reactivity of its carbothioamide moiety to build up the target thiazoles. Thus, compound 3 was conveniently cyclized in ethanolic solution to afford 2-(3-(3,5-diphenyl-4,5dihydro-1H-pyrazol-1-yl)-5-methyl-1H-1,2,4-triazol-1-yl)-4-phenylthiazole (11), in 76% yield, via treatment with phenacyl bromide (Scheme 2). In another investigation, the thiocarbamoyl 3 was cyclized into the thiazolone derivative 12 in 82% yield via treatment with chloroacetic acid in glacial AcOH containing NaOAc.…”

“…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.…”

“…The preliminary bioassay results indicate that the majority of the tested compounds exhibited significant antimicrobial activity. Compounds 12,11,18,30,22,3, and 2 were found to be the most potent against the tested microorganisms with minimum inhibitory concentration ≤ (12.25 μg/mL), indicating that conjugates bearing thiazole moiety, as well as those with Nsubstituted electron-withdrawing groups, exhibited higher potency than the rest of other compounds.…”

“…Herein, we reported the efficient synthesis of new azoles as bio-functional analogs, employing the easily obtainable N-acetyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (1), as a versatile precursor. The structures of the newly synthesized compounds were elucidated based on their IR, 1 H NMR, and 13 C NMR mass spectral and elemental analysis. Furthermore, some selected compounds were evaluated in vitro for their antimicrobial activities.…”