Banca de DEFESA: BRUNA MARTINS GUIMARÃES

Uma banca de DEFESA de DOUTORADO foi cadastrada pelo programa.
STUDENT : BRUNA MARTINS GUIMARÃES
DATE: 31/08/2022
TIME: 09:00
LOCAL: Departamento de Química
TITLE:

SYNTHETIC PLANNING, STRUCTURAL ELUCIDATION AND BIOLOGICAL EVALUATION OF UNRELEASED 2,3-UNSATURATED O-GLYCOSIDES CANDIDATES FOR DRUG CANDIDATES WITH BIOACTIVE PROPERTIES

KEY WORDS:

O-glycoside. Ferrier rearrangement. 1,2,3-Triazole, Glycero-pyrimidines.

PAGES: 130
BIG AREA: Ciências Exatas e da Terra
AREA: Química
SUBÁREA: Química Orgânica
SPECIALTY: Síntese Orgânica
SUMMARY:

The aim of the present work was to synthesize new glycerol-triazole-pyrimidines from 2,3-unsaturated O-glycoside and azido-glycero-pyrimidine alcohol, as well as new 1,3-oxazolidine-2-thione derivatives from azido-glyceres -pyrimidines. First, the synthesis of the 2,3-unsaturated O-glycoside 33 was carried out through the Ferrier Rearrangement between glycerol carbonate and tri-O-acetyl-D-glucal. Then, a reaction with sodium azide provided azido-alcohol 34 in 85% yield. Subsequently, he joined the synthesis of 1,3-oxazolidine-2-tion 37 with a 51% yield in the presence of PPh3 and CS2. The triazole compounds were prepared via a “click” reaction between the mono 35a-c bis-alkylated 35d-f alkines, forming the mono 36a-c bis-substituted 36d-f triazoles with a certain 74-92% and 52-57% respectively. Following another strategy, we carried out the synthesis of glycerol-pyrimidines 42 (81%), 43 (72%) and 44 (17%) through the reaction between tosylated glycerol carbonate 8 and as properly protected pyrimidine bases uracil and thymine. Then, the pyrimidine glycers 42, 43 and 44 improved the reaction with sodium azide to open the carbonate ring and form the azido-alcohol-glycerides-pyrimidines 45, 46 and 47 with an adjustment of 74, 65 and 23%, respectively. The azido-alcohol-glycerides-pyrimidine 45 was subjected to “click” reaction to form the new pyrimidine triazoles 48 and 49 with yields 17 and 28% respectively. Compound 50 was synthesized and subjected to the same protocol as compound 37, obtaining 30% yield. Among these compounds, glycosides 36a-f were selected and tested against Zika virus. Vero and HepG2 cell lines were used and the compound 36d was considered more promising, showing a better selectivity index than 6MMPr.

BANKING MEMBERS:
Presidente - 1508305 - JOAO RUFINO DE FREITAS FILHO
Interno - 1178305 - CELSO DE AMORIM CAMARA
Interno - 3133784 - MARCILIO MARTINS DE MORAES
Interno - 2534469 - RONALDO NASCIMENTO DE OLIVEIRA
Externa à Instituição - IVANI MALVESTITI - UFPE
Externa à Instituição - SHALOM PORTO DE OLIVEIRA ASSIS - UNICAP