An effective green one-pot synthesis of some novel 5-(thiophene-2-carbonyl)-6-(trifluoromethyl)pyrano[2,3- <i>c</i> ]pyrazoles and 6-(thiophene-2-carbonyl)-7-(trifluoromethyl)pyrano[2,3- <i>d</i> ]pyrimidines bearing chromone ring as anticancer agents
Tarik E. Ali, Mohammed A. Assiri, Abdullah Yahya Abdullah Alzahrani, Mohamed A. Salem, Ali A. Shati, Mohammad Y. Alfaifi, Serag Eldin I. Elbehairi
Abstract
An effective green one-pot and catalyst-free synthesis of a series of novel 5-(thiophene-2-carbonyl)-6-(trifluoromethyl)pyrano[2,3-c]pyrazoles and 6-(thiophene-2-carbonyl)-7-(trifluoromethyl)pyrano[2,3-d]pyrimidines bearing chromone ring was achieved. The method depended on a one-pot three-component reaction of readily available starting materials 4-oxo-4H-chromene-3-carboxaldehyde, 2-thenoyltrifluoroacetone, and cyclic active methylene compounds in water as solvent. The targeted compounds were assessed for their in vitro anticancer activity against mammary gland breast cancer cell line (MCF-7), liver cancer (HepG-2), and human colon cancer (HCT-116) by using sulphorhodamine B assay (SRB) method, while doxorubicin, was utilized as standard reference drug. Compounds 4a, 4c, and 6b exhibited excellent anticancer activity versus all cancer cell lines with IC50 values ranging from 1.7 to 9.9 μg/mL.