Jayalakshmi Sridhar
Assistant Professor Xavier University of Louisiana, LA, USA
Title: Discovery of a synthetic method to form 2,2 - bis(naphthoquinones) compounds
Biography:
Jayalakshmi Sridhar has her expertise in organic synthesis of complex molecules and computational molecular modeling. Her research work group focuses on the development of modulators for three classes of proteins - (1) protein kinases that regulate many of the key signaling pathways in the cell, (2) the cytochrome P450 enzymes that metabolize exogenous and endogenous substances in the body and (3) Liver X Receptor b that is a key mediator in many of the cellular processes. The development of new synthetic methods for the target molecule is part of the research focus. The discovery of one such reaction trais a practical, efficient, and transition metal free approach to the synthesis of binaphthyltetraones using Diels-Alder reaction of substituted trimethylsilane dienes with benzoquinone.
Abstract:
Quinones are key structural components in many natural products, and therapeutic drugs impacting many disease conditions, viz antimicrobial, antiparasitic, anti-tumor, inhibition of PGE2 biosynthesis and anti-cardiovascular disease. As part of our efforts in the design and development of kinase inhibitors as potential therapeutics for cancer and Alzheimer’s disease, the synthesis of monohydroxynaphthoquinones using Diels-Alder reaction was pursued. This lead to the discovery of a novel method for the synthesis of 2,2’-bis(naphthoquinones) using conjugated ketene silyl acetals with benzoquinone. The analysis of the reaction conditions and the product structures using NMR and X-ray lead to the elucidation of a credible mechanism of dimer formation. The control of reactant stoichiometry to yield either the monomer of the dimer product is explored. The results of the study of this new synthetic method are presented.