One-pot multicomponent synthesis of novel 1-thiazolyl-5-coumarin-3-yl-pyrazole derivatives and evaluation of their cytotoxic activity

Abstract

A series of novel 1-thiazolyl-5-coumarin-3-yl-pyrazole derivatives (4a-l) were synthesized via one-pot multicomponent reaction of 5-substituted salicylaldehydes (1a-c), 4-hydroxy-6-methyl-2H-pyran-2-one (2) and 2-hydrazinyl-4-arylthiazoles (3a-d) in acetonitrile using a catalytic amount of piperidine under reflux conditions. This multicomponent approach has advantages such as reduced reaction time and a high product yield percentage when compared with corresponding multistep approaches. All the synthesized compounds were evaluated for their cytotoxic activity against Hep G2 (hepatocellular liver carcinoma) and MCF-7 (breast cancer) cell lines and compared with the standard drug Doxorubicin. Among all the compounds, compounds 4d against Hep G2, 4k against MCF-7 and 4e against both Hep G2 & MCF-7 showed excellent cytotoxic activity.

Latest developments in coumarin-based anticancer agents: mechanism of action and structure–activity relationship studies

“…Twelve novel 1-thiazolyl-5-coumarin-3-yl-pyrazole derivatives were developed via a one-pot multicomponent reaction and their anticancer activity was investigated on two cancer cell lines (HepG2 and MCF7). 90 Compound 44a ( Fig. 39 ) showed significant cytotoxic activity against the HepG2 cell line with an IC 50 value of 3.74 ± 0.02 μM and 44b possessed significant activity against MCF-7 with an IC 50 value of 4.03 ± 0.02 μM.…”

Current developments of coumarin-based anti-cancer agents in medicinal chemistry

“…These compounds also showed better activity toward MCF7 than the remaining compounds. However, their activities were less than that of doxorubicin against MCF7 [170].…”

Novel Coumarin‐Pyrazole‐Thiazoles Hybrids: Synthesis, Anticancer Activity, Molecular Docking and In Silico ADMET prediction Studies

“…The significant inhibitory effects of these compounds on various cancer cell lines have generated considerable excitement among drug designers (Figure 3). [34–38] These findings highlighted the potential of these coumarin‐thiazole‐pyrazole molecules as promising leads for developing novel cancer therapies.…”