Synthesis, biological activity evaluation and molecular docking studies of novel coumarin substituted thiazolyl-3-aryl-pyrazole-4-carbaldehydes. Issue 24 (15th December 2015)

• Record Type: Journal Article
• Authors: Vaarla, Krishnaiah; Kesharwani, Rajesh Kumar; Santosh, Karnewar; Vedula, Rajeswar Rao; Kotamraju, Srigiridhar; Toopurani, Murali Krishna
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 25:Issue 24(2015)
• Page Start: 5797
• Page End: 5803
• Publication Date: 2015-12-15
• Subjects: 3-(2-Bromoacetyl)coumarins -- Thiosemicarbazide -- Thiazolyl-pyrazoles -- Vilsmeier–Haack formylation -- Anti cancer activity -- Docking; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.10.042
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A novel series of coumarin substituted thiazolyl-3-aryl-pyrazole-4-carbaldehydes (4a –o ) were synthesized via an efficient, one-pot multicomponent approach involving 3-(2-bromoacetyl)coumarins (1a –g ), thiosemicarbazide (2 ) and substituted acetophenones (3a –c ) utilizing Vilsmeier–Haack reaction condition with good yields. The title compounds structure was elucidated by spectroscopic data (IR, NMR and Mass) and elemental analysis. All the synthesized compounds were screened for their in vitro cytotoxic activity against MCF-7, DU-145 and HeLa cell lines and studied detailed about molecular interaction of probable target protein human microsomal cytochrome CYP450 2A6 using docking simulation. These coumarin derivatives were exhibiting moderate to appreciable cytotoxic activities. The compounds4m and4n exhibited significant cytotoxic activity with IC50 values having 5.75 and 6.25 μM against HeLa cell line. Similarly compound4n also exhibiting good anti cancer property and antibacterial activity against DU-145 cell line and Gram negative bacterial strains.