Post-Functionalization of Small Ply-functionalized Molecules: A Robust Approach to the Synthesis of New Structural Patterns with POtential Biological Activity

Abstract

This research project intends to continue the development of a line of research that explores the Morita-Baylis-Hillman (MBH) reaction, which is an organocatalysed process of formation of a new C-C Ã bond, leading to the synthesis of small poly-functionalized, which can be used as substrate for other chemical transformations. The research proposal was divided into two main projects and each of them divided into subprojects. In the first project, we intend to explore the general aspects of this reaction by initially testing its behavior in the presence of Bronsted acids. Although the usual catalysts of the Morita-Baylis-Hillman reaction may give rise to a very rapid acid-base reaction, preliminary results show a considerable increase in both the reaction rate and the yields, especially with aromatic aldehydes substituted with electrons donating groups, which behave very badly in this reaction. We also intend to explore novel bi-functional Lewis bases as catalysts for an asymmetric version of an MBH reaction between isatin and cycloenones. In the second project we intend to explore the use of adducts as substrates for the synthesis of pyrido-indolones, poly-functionalized dienes, macrolactones and macrolactams using novel synthetic approaches. The products obtained in this part of the proposal will be evaluated against triple negative human breast cancer cells. They will also be evaluated as inhibitors of acetylcholinesterase and against the parasites that cause malaria and leishmaniasis. (AU)