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

ABSTRACT

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 oxa- di-pi-methane rearrangement. We are also concerned to explore a route to tetracyclic core (1e) 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. © 2021 The Author(s)