Synthesis, characterization, anti-cancer and anti-bacterial study of isatin conjugated 4-azidopyrazoline derivatives

Reddy Raghunath Babu; Radhika T.; Tejaswini B.; Madhava Reddy B.; Harinadha Babu V

Abstract

Synthesis, characterization, anti-cancer and anti-bacterial study of isatin conjugated 4-azidopyrazoline derivatives

Author(s): Reddy Raghunath Babu, Radhika T., Tejaswini B., Madhava Reddy B. and Harinadha Babu V

New derivatives of isatin conjugated 4-azidopyrazolines were synthesized 5(a-e) and characterized by physical and spectral data. From p-aminoacetophenone, 1-(4-azidophenyl)ethanone (1) was prepared by diazotization and subsequent reaction with sodium az ide. Claisen-Schmidt condensation of compound (1) with different aromatic/hetero aldehydes gave chalcones 2(a-e) which were converted into pyrazolines 3(a-e) using hydrazine hydrate and treated with chloroacetyl chloride to give 1-(3-(4-azidophenyl-5-(4-aryl/hetero aryl)-4,5-dihydro-1Hpyrazol- 1-yl)-2-chloroethanones 4(a-e). Condensation of compounds 4(a-e) with isatin gave the final compounds 5(a-e). The synthesized compounds were evaluated for anti-bacterial and in vitro anti-cancer properties. Among the five compounds, 5b&5d showed significant activity against p.aeruginosa with MIC values at 6.25 and 12.5 μg/ml. In MTT assy for cytotoxicity activity, compound 5a showed highest activity against NCI-H23 and MCF-7 cell lines with IC50 values at 1.06 & 3.92 μM/ml, while the other compounds were moderately active with IC50 values >20 μM/ml. In vivo anticancer activity studies against Ehrlich ascites carcinoma (EAC) revealed that compound 5a has highest increase in life span (% ILS) and mean survival time (MST) with 73.47 % and 31.5 ± 0.48 days respectively. A good correlation was observed between the results of in vitro and in vivo anticancer study of the compounds.

PDF

Select your language of interest to view the total content in your interested language