Banca de QUALIFICAÇÃO: RAYANE DE OLIVEIRA SILVA

Uma banca de QUALIFICAÇÃO de DOUTORADO foi cadastrada pelo programa.
STUDENT : RAYANE DE OLIVEIRA SILVA
DATE: 28/02/2022
TIME: 14:30
LOCAL: Videoconferência
TITLE:

RATIONAL PLANNING OF NEW CARBOHYDRATES APPLIED AS ANTINEOPLASTIC, ANTIMICROBIAL AND ANTIVIRAL

KEY WORDS:

Natural Products, 2,3-Unsaturated O-Glycosides, In Silico Study, Biological Activity

PAGES: 111
BIG AREA: Ciências Exatas e da Terra
AREA: Química
SUBÁREA: Química Orgânica
SPECIALTY: Síntese Orgânica
SUMMARY:

Conducting a prospection, it appears that most of the commercialized drugs are structures analogous to the natural products found in different types of living organisms. Among the different sources of natural products, plants stand out, since they act as "true factories generating" this class of chemical substances. Natural products and their derivatives have interesting characteristics such as high chemical diversity and biochemical specificity. In view of these and other functions performed by natural products, this work consisted of the synthesis of bioactive compounds derived from D-glucose in order to evaluate their biological and pharmacological activities. The synthetic strategy adopted consisted of the reaction of transforming D-glucose into 3,4,6-tri-O-acetyl-D-glucal, which, in turn, was sequentially submitted to the Glycosylation Reaction, Hydrolysis Reaction, Oxidation Reaction and Allylation Reaction. In order to facilitate the reading and exposition of the results, the work was structured in three chapters that complement each other in essence. As a result of chapter 1, 30 scientific articles were analyzed, highlighting the synthesis of natural products from 3,4,6-tri-O-acetyl-D-glucal, in which all analyzed studies were successful in the synthesis of the compounds under study. Regarding the results of Chapter 2, 3,4,6-tri-O-acetyl-D-glucal was synthesized with 94% yield, which was subjected to Ferrier rearrangement with menthol leading to the formation of O-glycoside 2,3-unsaturated in 90% yield. The 2,3-unsaturated O-glycoside was subjected to a hydrolysis reaction using the protocol developed by our research group, obtaining the hydrolyzate with a yield of 89%, then it was subjected to an allylic oxidation reaction, in which the oxide of manganese was used as a reducing agent, obtaining the hydrolyzate with a yield of 76%. Finally, an in silico study was carried out, in which the results demonstrate the high potential of these compounds from the point of view of medicinal chemistry, demonstrating good absorption and pharmacokinetic patterns linked to good toxicological characteristics. Regarding the results of Chapter 3, the synthesis of 2,3-unsaturated O-glycosides led to the formation of compounds with yields ranging from 80 to 96%. Then, the hydrolysis and allylic oxidation reaction was carried out, which led to the formation of the respective compounds with yields ranging from 70 to 91%. Then, the synthesis of the allylation reaction of compound 7d was carried out, it was obtained with the appearance of a white solid, with a yield of 75%. Finally, all compounds were submitted to analysis of infrared radiation, nuclear magnetic resonance of hydrogen and carbon-13, in which the analyzes of the data obtained corroborate the proposed structures and are in agreement with the literature data.

BANKING MEMBERS:
Interno - 1508305 - JOAO RUFINO DE FREITAS FILHO
Externa ao Programa - 094.685.304-50 - JOSEFA AQUELINE DA CUNHA LIMA - UFCG
Presidente - 054.451.424-69 - JULIANO CARLO RUFINO DE FREITAS - UFCG
Interno - 3133784 - MARCILIO MARTINS DE MORAES
Externo ao Programa - 316.284.193-34 - PAULO SÉRGIO - UFCG