Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide

Abstract

Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 4a-g and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 5a-k were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC 50 ) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-N-p-tolylhydrazine carbothioamide (5b) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds.

Crystal structure of (Z)-4-benzyl-N'-(4-chloro-2-oxoindolin-3-ylidene)-piperazine-1-carbothiohydrazide, C20H20ClN5OS

“…Substituted indolin-2-ones have been identified as a versatile scaffold which exhibit diverse chemotherapeutic activities such as anticancer, antiviral and many others properties [1][2][3]. Among them, 1H-indole-2,3-dioxo-3-thiosemicarbazones have in general been reported to possess antitumour activities [3,4].…”

“…Among them, 1H-indole-2,3-dioxo-3-thiosemicarbazones have in general been reported to possess antitumour activities [3,4]. Our previous studies have revealed the promising cytotoxic properties of various piperazine-1-carbothiohydrazide-based derivatives of indolin-2-one [5].…”

Microwave Assisted Synthesis and Microbial Evaluation of -2h-Pyrrolo [2, 3-C: 5, 4 C'] Dipyrazole-2, 5 (7h)-Bis-Carbothioamide Derivatives

“…The IR starching band obtained at 1705.03 cm -1 is due to presence of C=C in conjugation with C=O groups. 1 HNMR spectrum of chalcone derivatives shown peak at 2.3 δ singlet due to presence of -CH 3 group at aromatic ring and peak obtained at 7.6-7.2 δ multiplate indicates the presence of 6H aromatic proton Ar-H and 1H of =CH methyne proton. Similarly 13 C NMR spectrum showed that peak at 180 δ corresponds to presence of carbonyl carbon.…”

“…Journal of Advanced Scientific Research, 2022; 13 (1): Feb.-2022 3345.28 cm -1 is due to presence of (-NH 2 ) group. The 1 H NMR spectral analysis of compound 9bii showed peak at 2.67 δ doublet 2H, for-CH Pyrazole and peak obtained at 3.45 δ doublet, 2H, indicate the presence of -CH Pyrazole which clearly indicated the formation of five membered pyrazole ring.…”

“…The substituted pyrazole is an important class of heterocyclic compounds and the pyrazole carbothioamide has remarkable applications in the field of medicine and drug designing. It shows antimycobacterial activity used for treatment of pulmonary tuberculosis [1][2], Cytostatic [3], Anti-inflammatory [4][5], Antifungal [6][7], Anti-malarial [8][9] and antiamoebic activities [10]. The pyrazole carbothiamide ring is present as the core in variety of leading drug.…”