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Efficient Green Synthesis, Anticancer Activity, and Molecular Docking Studies of Indolemethanes Using a Bioglycerol-Based Carbon Sulfonic Acid Catalyst

Sailam Sri Gogula, Dasari Vijaya Prasanna, Vishnu Thumma, Sunil Misra, Ch. Abraham Lincoln, P. Muralidhar Reddy, Anren Hu, B. V. Subba Reddy

2023ACS Omega16 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide Indolemethane derivatives are significant molecules in the study of N -heterocyclic chemistry. Herein, we designed and developed a highly efficient green synthesis of indolemethane compounds using a recyclable biodegradable glycerol-based carbon solid acid catalyst under solvent-free conditions at room temperature for 5 min with excellent yields. The synthesized compounds were subjected to cytotoxic activity against prostate (DU145), hepatocellular carcinoma (HepG2), and melanoma (B16) cell lines. The highest cytotoxicity effects were found with 1k (1.09 μM) and 1c (2.02 μM) against DU145, followed by 1a, 1d, 1f, 1n, and 1m between 5.10 and 8.18 μM concentrations. The anticancer activity is validated using molecular docking simulations, and comparing binding energies with the standard drug doxorubicin suggests that the title compounds are well fitted into the active site pocket of the target molecules..

Topics & Concepts

DU145ChemistryCatalysisMoleculeCytotoxicityCombinatorial chemistryDocking (animal)Hepatic carcinomaSolventAnticancer drugGlycerolDoxorubicinNuclear chemistryStereochemistryOrganic chemistryDrugIn vitroBiochemistryPharmacologyLNCaPCancerNursingCancer cellSurgeryChemotherapyInternal medicineMedicineSynthesis of Indole DerivativesMulticomponent Synthesis of HeterocyclesSynthesis and biological activity