ABSTRACT
BACKGROUND: The Morita-Baylis-Hillman reaction (MBHR) is considered one of the most powerful and versatile methodologies used for carbon-carbon bond formation. The reaction is defined as the condensation between an electrophilic carbon sp² and the α position of an olefin, carrying an electron-withdrawing group, in the presence of a catalyst. The advantages of the reaction are the high atom economy and mild reaction conditions. Under ideal conditions, this reaction leads to the formation of multifunctional products, called Morita-Baylis-Hillman adducts (MBHA), a class of relevant molecules that exhibit a variety of biological activities. OBJECTIVE: Considering the importance of these compounds, this review brought together several studies regarding the biological activities of MBHA, to point out the use of these molecules as future therapeutic agents. METHODS: We searched for scientific articles available in the main databases, published between 1999 and 2022, using the descriptors: Morita-Baylis-Hillman adducts, Morita-Baylis-Hillman reaction, biological activity, and biological potentiality. RESULTS: Thirty-five articles showed the variety of biological activities of MBHA, including molluscicidal, antitumor, herbicidal, and fungicidal, antileishmanial, antioxidant, antimalarial, anti-tumor inflammatory, vasorelaxant, antichagasic, antimicrobial, and anti-inflammatory activities. CONCLUSION: Therefore, these compounds are promising candidates to become drugs for the treatment of a variety of diseases, following further studies to understand the effective mechanisms of action of MBHA.
Subject(s)
Antimalarials , Antiprotozoal Agents , Antiprotozoal Agents/chemistryABSTRACT
Giardiasis is a neglected disease, and there is a need for new molecules with less side effects and better activity against resistant strains. This work describes the evaluation of the giardicidal activity of thymol derivatives produced from the Morita-Baylis-Hillman reaction. Thymol acrylate was reacted with different aromatic aldehydes, using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a catalyst. Eleven adducts (8 of them unpublished) with yields between 58 and 80% were obtained from this reaction, which were adequately characterized. The in silico prediction showed theoretical bioavailability after oral administration as well as antiparasitic activity against Giardia lamblia. Compound 4 showed better biological activity against G. lamblia. In addition to presenting antigiardial activity 24 times better than thymol, this MBHA was obtained in a short reaction time (3 h) with a yield (80%) superior to the other investigated molecules. The molecule was more active than the precursors (thymol and MBHA 12) and did not show cytotoxicity against HEK-293 or HT-29 cells. In conclusion, this study presents a new class of drugs with better antigiardial activity in relation to thymol, acting as a basis for the synthesis of new bioactive molecules. Molecular hybridization technique combined with the Morita-Baylis-Hillman reaction provided new thymol derivatives with giardicidal activity superior to the precursor molecules.
Subject(s)
Giardia lamblia , Thymol , Aldehydes , Catalysis , HEK293 Cells , Humans , Thymol/pharmacologyABSTRACT
A qualidade microbiológica deleites cru e pasteurizado produzidos e comercializados em São Luís MA foi avaliada por meio da quantificação e identificação de cepas de micro-organismos do gênero Staphylococcus. Verificou-se um alto nível de contaminação por Staphylococcus sp. em 60% das amostras de leite cru analisadas, com as contagens variando entre 1,7x105 e 1,1x107 UFC/mL, sendo comprovada a presença de Staphylococcus coagulase positiva nessas amostras. No leite pasteurizado foram obtidas baixas contagens desse micro-organismo, com valores variando entre 2,7x102 e 4,2x102 UFC/mL, não sendo detectados Staphylococcus coagulase positiva, apenas coagulase negativa em 23% (n=3) das amostras analisadas. As colônias características de Staphylococcus isoladas foram identificadas por meio de testes bioquímicos convencionais. Das 50 cepas isoladas, 38% foram positivas para o teste de coagulase, sendo identificadas as espécies S. aureus, S. hyicus, S. intermedius e S. delphini. Entre as cepas de Staphylococcus coagulase negativa, verificou-se a predominância das espécies S. gallinarum, S. cloosii, e S. xylosus. A presença de tais micro-organismos no leite é preocupante do ponto de vista da segurança dos alimentos, tendo em vista que espécies como S. aureus, S. hyicus e S. intermedius são potenciais produtoras de enterotoxinas termoestáveis.
The microbiological quality of raw and pasteurized milk produced and sold in São Luís MA was evaluated through quantification and identification of Staphylococcus cepes. A high level contamination by Staphylococcus sp. was verified in 60% of samples of raw milk, counting varying between 1.7 × 105 e 1.1 × 107 CFU/mL, which proves the presence of positive coagulasis Staphylococcus in these samples. In the pasteurized milk low counting of this microorganism was obtained, values varying between 2.7 × 102 e 4.2 × 102 CFU/mL, in where it was not found positive coagulase Staphylococcus, but only negative ones in 23% (n=3) of the analyzed samples. The typical colonies of isolated Staphylococcus were identified through conventional biochemical tests. From 50 isolated cepes, 38% were positive for coagulase test, in which S. aureus, S. hyicus, S. intermedius e S. delphini species were identified. Among the cepes of negative coagulase Staphylococcus6, S. gallinarum, S. cloosii, e S. xylosus were predominant. The presence of these microorganisms in milk is a motive to be worried about concerning food safety, for species like S. aureus, S. hyicus e S. intermedius are potential producers of thermostable enterotoxins.