Synthesis of biologically active fused 1,4-oxathiin derivatives from 4-hydroxydithiocoumarins, arylacetylenes and dimethyl sulfoxide by Cu(<scp>i</scp>)-catalyzed C–H functionalization and cross-dehydrogenative C–S coupling reactions
Santa Mondal, Sabina Yashmin, Rashid Ali, R Soundaram, Siddhartha Sankar Ghosh, Abu T. Khan
Abstract
in an oil bath at 70 °C. The novelties of the present protocol are (i) selective C-H functionalization at the C-3 position of 4-hydroxydithiocoumarin, (ii) regioselective hydrothiolation with arylacetylenes and (iii) concomitant cyclisation. The major advantages are mild reaction conditions, broad substrate scope and good yield. Among the synthesized compounds, the following five compounds 3aa, 3bd, 3ec, 3fa, and 3fd showed anticancer activity against a human breast cancer cell line (MCF-7) and a cervical cancer cell line (HeLa).
Topics & Concepts
HeLaChemistryDimethyl sulfoxideRegioselectivityArylYield (engineering)SulfoxideCatalysisSubstrate (aquarium)Cancer cell linesMedicinal chemistrySurface modificationCombinatorial chemistryCoupling reactionStereochemistryOrganic chemistryIn vitroCancer cellAlkylCancerBiochemistryMaterials scienceGeologyOceanographyMetallurgyMedicinePhysical chemistryInternal medicineCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions