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Semi-synthesis of heteroaromatic derivatives of (-)-palitantin for obtaining bioactive analogues

Grant number: 21/13089-6
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): February 01, 2022
Effective date (End): January 31, 2023
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Roberto Gomes de Souza Berlinck
Grantee:Beatriz Gabrieli Sampaio
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
Associated research grant:19/17721-9 - The role of Chemistry in holobiont adaptation, AP.TEM

Abstract

Palitantin is a secondary metabolite originally isolated from cultures of the fungus Penicillium palitans, and it is also produced by other fungal species. A fungal strain, Geomyces sp., from Antarctica, produces (-)-palitantin in a yield of about 170 mg/L, which allows the isolation of this compound to be used on a larger scale for the preparation of derivatives. As the synthesis routes for palitantin developed so far are multi-step, with yields of at most 45% and use reagents that are generally expensive and harmful to the environment, the production of palpitation via fermentation is a good alternative for obtaining it on a grams scale. Palitantin is similar to frequently, originally isolated from the fungus Penicillium frequents. Both showed antifungal activity against several fungal strains. This project aims to prepare synthetic heteroaromatic derivatives of (-)-palpitation, containing a pyrimidine nucleus, for the evaluation of their biological activity in bioassays of antibacterial activity against antibiotic-resistant and susceptible bacteria, of antifungal activity, of antiparasitic activity against Plasmodium falciparum, Leishmania spp. and Trypanosoma cruzi, as well as cytotoxic action on tumor cells. (AU)

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