Total Synthesis of (-)-Brussonol, (+)-Komaroviquinona and its analogs targeting potential candidates with trypanocidal activity

• Grant number: 15/20084-0
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: April 01, 2016
• End date: April 30, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Anees Ahmad
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Associated research grant: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors, AP.TEM

Abstract

The proposal aims the total synthesis of the diterpenes (-)-Brussonol and (+)-Komaroviquinone, as well as possible analogs and their racemic forms. The main steps of this proposal constitute the epoxide-opening as well as a intramolecular Friedel-Crafts reaction. It is noteworthy that these steps were never previously employed for the construction of this type of skeleton and may be applied to other substances of similar structure. Furthermore, this study can promote the development of a new methodology for the opening of congested epoxides from oxygenated aromatic rings. Synthesizing these compounds and their analogs, the evaluation of their trypanocidal activity will be carried out.

Scientific publications

(5)

(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)

GALLO, RAFAEL D. C.; CAMPOVILLA, JR., ORLANDO C.; AHMAD, ANEES; BURTOLOSO, ANTONIO C. B.. Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis. FRONTIERS IN CHEMISTRY, v. 7, FEB 8 2019. (15/20084-0, 17/23329-9, 13/18009-4)

KHALID, MUHAMMAD; ALI, AKBAR; KHAN, MUHAMMAD USMAN; TAHIR, MUHAMMAD NAWAZ; AHMAD, ANEES; ASHFAQ, MUHAMMAD; HUSSAIN, RIAZ; DE ALCANTARA MORAIS, SARA FIGUEIREDO; CARMO BRAGA, ATAUALPA ALBERT. Non-covalent interactions abetted supramolecular arrangements of N-Substituted benzylidene acetohydrazide to direct its solid-state network. Journal of Molecular Structure, v. 1230, APR 15 2021. (15/20084-0)

AHMAD, ANEES; BURTOLOSO, ANTONIO C. B.. Total Synthesis of (+/-)-Brussonol and (+/-)-Komaroviquinone via a Regioselective Cross-Electrophile Coupling of Aryl Bromides and Epoxides. ORGANIC LETTERS, v. 21, n. 15, p. 6079-6083, AUG 2 2019. (15/20084-0, 17/23329-9, 13/18009-4)

BARBOSA, CAMILA S.; AHMAD, ANEES; MALUF, SARAH EL CHAMY; MOURA, IGOR M. R.; SOUZA, GUILHERME E.; GUERRA, GIOVANNA A. H.; BARROS, ROBERTO R. MORAES; GAZARINI, MARCOS L.; AGUIAR, ANNA C. C.; BURTOLOSO, ANTONIO C. B.; et al. Synthesis, Structure-Activity Relationships, and Parasitological Profiling of Brussonol Derivatives as New Plasmodium falciparum Inhibitors. PHARMACEUTICALS, v. 15, n. 7, p. 21-pg., 2022-07-01. (13/07600-3, 21/03977-1, 20/14429-2, 19/17721-9, 19/19708-0, 20/12904-5, 18/06219-8, 15/20084-0, 18/07287-7, 13/18009-4, 21/14319-5)

GALLO, RAFAEL D. C.; CAMPOVILLA, ORLANDO C., JR.; AHMAD, ANEES; BURTOLOSO, ANTONIO C. B.. Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis. RONTIERS IN CHEMISTR, v. 7, p. 7-pg., 2019-02-08. (13/18009-4, 15/20084-0, 17/23329-9)