Banca de DEFESA: MAURICÉLIA MARIA DE SOUSA MATA

Uma banca de DEFESA de DOUTORADO foi cadastrada pelo programa.
STUDENT : MAURICÉLIA MARIA DE SOUSA MATA
DATE: 17/11/2022
TIME: 14:00
LOCAL: Departamento de Química
TITLE:

1,2,4-Oxadiazoles and S-2,3-Unsaturated Glycosides: Synthesis and Structural Characterization

KEY WORDS:

Amidoximes, 1,2,4-oxadiazoles, 2,3-unsaturated glycosides.

PAGES: 94
BIG AREA: Ciências Exatas e da Terra
AREA: Química
SUMMARY:

The 1,2,4-oxadiazoles are heterocyclics that have numerous pharmacological activities such as anti-inflammatory, larvicidal and fungicidal, among others. Undoubtedly, the biological properties conferred on 3,5-disubstituted 1,2,4-oxadiazoles added to the intermediation of the 2,3-unsaturated glycoside make the 2,3-unsaturated O and S-glycosides having an aglycone unit 1,2,4 -oxadiazoles in a potential source of new drugs. The present work describes the synthesis and characterization of new 1,2,4-oxadiazoles-3,5-disubistuted monos, and new 2,3-unsaturated O and S-glycosides through ring-linked Ferrier Rearrangement 1,2, 4-oxadiazole in the aglyconic part. A priori, the synthesis of the starting compounds was performed: 51a-i (amidoximes) and isopropyl 3-mercaptopropionate. The synthesis of arylamidoximes 51a-i was carried out starting from 49a-i (nitriles) with hydroxalamine hydrochloride and sodium carbonate as base. Products 55a-i were obtained in moderate to good yields (30% - 97%).Isopropyl 3-mercaptopropionate was obtained by Fischer's esterification reaction of propionic 3-mercapto acid, with isopropyl alcohol employing sulfuric acid as catalyst, which was obtained with a satisfactory yield of 75%. On the other hand, the synthesis of 1,2,4-oxadiazole 7a-d was developed, lasting 10 minutes, using microwave irradiation providing the compounds in moderate yields. The structures of 55a-i were characterized by infrared and nuclear magnetic resonance techniques (1H and 13C NMR). The cytotoxic evaluation was performed against Artemia salina, where it was found that the mortality percentage varied from 75-100% in all concentrations. As for antimicrobial activity, it was found that the compound 55c was the most active against the bacteria Staphylococcus aureus and Enterococcus faecalis (Gram-positive). All compounds demonstrated a good ability to inhibit the growth of Escherichia coli (Gram-negative) bacteria.

BANKING MEMBERS:
Interno - ALEX SOUZA MORAES
Presidente - JOAO RUFINO DE FREITAS FILHO
Externo à Instituição - JONH ANDERSON MACÊDO SANTOS
Externo ao Programa - 3022573 - JUCLEITON JOSE RUFINO DE FREITAS - nullExterno à Instituição - JULIANO CARLO RUFINO DE FREITAS - UFCG
Externo ao Programa - 3133784 - MARCILIO MARTINS DE MORAES - null