An efficient synthesis towards the core of Crinipellin: TD-DFT and docking studies

In this present report, we are describing a novel route for the synthesis of the tetracyclic ring systems, a common core of crinipellin, via oxidative dearomatization, cycloaddition and oxadi-pi-methane rearrangement. We are also concerned to explore a route to tetracyclic core (le) of Crinipellin and tricyclic core (1g) of Allicaol B through intermolecular diels alder reaction and photochemically 1,2 acyl shift. Moreover, docking study of compound 13 and 16 is investigated against AcrB multidrug efflux pump of Escherichia coli (PDB ID: 1T9U), main protease of SARS COV-2 (PDB ID: 6W63), DNA gyrase of Streptococcus pneumonia (PDB ID: 4Z2C), human estrogen receptor alpha (PDB ID: 3ERT), human lanosterol 14-alpha-demethylase (CYP51)(PDB ID: 3JUS) and cyclooxygenase-2 (Prostaglandin Synthase-2) (PDB ID: 1CX2). The obtained results are important for the exploitation of the therapeutic potential of these derivatives as antimicrobial, antiviral, anticancer, antifungal or anti-inflammatory agents. In addition, TD-DFT studies of the compounds are also carried out. (C) 2021 The Author(s). Published by Elsevier B.V.

Automated summary

This study explores a novel synthesis route for crinipellin and investigates its pharmacological effects, suggesting the potential of these compounds as therapeutic agents for various diseases.