Morita-Baylis-Hillman in medicinal chemistry: synthesis and neuroprotective, antimicrobial and antitumoral biological evaluations of new heterocycles, oximes and nitrones

• Grant number: 12/24783-1
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: May 01, 2013
• End date: April 29, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Fernando Antonio Santos Coelho
• Grantee: Rosimeire Coura Barcelos
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated scholarship(s): 14/16516-9 - New catalytic reactions for the construction of peptides and carbohydrate hybrids, BE.EP.PD

Abstract

Heterocyclic compounds, oximes and nitrones display a relevant role in several areas of the chemical industry, with special emphasis on the pharmaceutical industry. In this context, the development of new strategies that allow easy and quick access to these classes of compounds becomes highly desirable. For this purpose, Morita-Baylis-Hillman (MBH) adducts emerge as potential building blocks.This project aims to develop a synthetic approach employing MBH adducts as substrates for the preparation of heterocycles exhibiting different substitution patterns, as well as O-alkylated oximes and nitrones. Another objective is to develop an asymmetric strategy for the preparation of ²-hydroxy-±-aminoesters from chiral MBH adducts.This project will contribute to expanding the frontiers of the use of MBH adducts as simple and direct substrates for the synthesis of biologically active molecules and chiral building blocks for organic synthesis. Furthermore, the set of molecules prepared should be used as a basis for virtual screening using some important molecular targets associated with inflammation and cancer, and their antiproliferative, cytoprotective and antimicrobial activities will be evaluated. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

BARCELOS, ROSIMEIRE C.; ZEOLY, LUCAS A.; RODRIGUES, JR., MANOEL T.; FERREIRA, BRUNO R. V.; EBERLIN, MARCOS N.; COELHO, FERNANDO. Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS). MONATSHEFTE FUR CHEMIE, v. 146, n. 9, p. 1557-1570, SEP 2015. (12/24783-1)

ZEOLY, LUCAS A.; BARCELOS, ROSIMEIRE C.; RODRIGUES, JR., MANOEL T.; GOMES, RALPH C.; COELHO, FERNANDO. An improved method for the regioselective synthesis of highly substituted quinolines from Morita-Baylis-Hillman adducts. Tetrahedron Letters, v. 56, n. 22, p. 2871-2874, MAY 27 2015. (13/07600-3, 12/24783-1)