RESUMO
Microwave irradiation has become a popular heating technique in organic synthesis, mainly due to its short reaction times, solventless reactions, and, sometimes, higher yields. Additionally, microwave irradiation lowers energy consumption and, consequently, is ideal for optimization processes. Moreover, there is evidence that microwave irradiation can improve the regioselectivity and stereoselectivity aspects of vital importance in synthesizing bioactive compounds. These crucial features of microwave irradiation contribute to its inclusion in green chemistry procedures. Since 2003, the use of microwave-assisted organic synthesis has become common in our laboratory, making our group one of the first Portuguese research groups to implement this heating source in organic synthesis. Our achievements in the transformation of heterocyclic compounds, such as (E/Z)-3-styryl-4H-chromen-4-ones, (E)-3-(2-hydroxyphenyl)-4-styryl-1H-pyrazole, (E)-2-(4-arylbut-1-en-3-yn-1-yl)-4H-chromen-4-ones, or (E)-2-[2-(5-aryl-2-methyl-2H-1,2,3-triazol-4-yl)vinyl]-4H-chromen-4-ones, will be discussed in this review, highlighting the benefits of microwave irradiation use in organic synthesis.
Assuntos
Cromonas/síntese química , Calefação/métodos , Micro-Ondas , Pirazóis/síntese química , Quinolonas/síntese química , Química Farmacêutica/métodos , Cromonas/efeitos da radiação , Técnicas de Química Combinatória/métodos , Inibidores Enzimáticos/síntese química , Humanos , Estrutura Molecular , Pirazóis/efeitos da radiação , Quinolonas/efeitos da radiaçãoRESUMO
Infections caused by pathogenic bacteria, especially the drug-resistant bacteria, are posing a devastating threat to public health, which underscores the urgent needs for advanced strategies to effectively prevent and treat these intractable issues. Here we report a feasible and effective theranostic platform based on an enzyme-sensitive and photoactivatable carbon monoxide releasing molecule (CORM-Ac) for the successive detection and elimination of bacterial infection. The extracellular bacterial lipase can trigger the excited state intramolecular proton transfer (ESIPT) via elimination of the ester group in CORM-Ac, thus providing a fluorescence switch for an early warning of infection. Subsequently, the potent bactericidal therapy against the model bacterial strains, Staphylococcus aureus (S. aureus) and notorious methicillin-resistant Staphylococcus aureus (MRSA), was readily realized via photoinduced release of CO. In addition, the CORM-Ac and CORM showed good biocompatibility within a wide range of concentrations. The results of an infected animal wound test also demonstrated that the CORM-Ac-loaded gauze was effective in indicating the wound infection and accelerating the wound healing via the photoinduced CO release. The simplicity, functional integration, good biocompatibility and broad adaptability make CORM-Ac very attractive for bacterial theranostic applications.
Assuntos
Antibacterianos/farmacologia , Monóxido de Carbono/metabolismo , Cromonas/farmacologia , Corantes Fluorescentes/farmacologia , Infecções Cutâneas Estafilocócicas/diagnóstico por imagem , Infecções Cutâneas Estafilocócicas/tratamento farmacológico , Animais , Antibacterianos/síntese química , Antibacterianos/metabolismo , Antibacterianos/efeitos da radiação , Proteínas de Bactérias/metabolismo , Hidrolases de Éster Carboxílico/metabolismo , Cromonas/síntese química , Cromonas/metabolismo , Cromonas/efeitos da radiação , Feminino , Fibroblastos/efeitos dos fármacos , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/metabolismo , Corantes Fluorescentes/efeitos da radiação , Luz , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Camundongos Endogâmicos BALB C , Testes de Sensibilidade Microbiana , Imagem Óptica , Medicina de Precisão/métodos , Estudo de Prova de ConceitoRESUMO
3-Arylthiochromone derivatives were synthesized as new photolabile protecting groups, in which the photoreactivity was switchable based on oxidation of the sulfur atom (sulfide and sulfone); the protected substrates , released the corresponding alcohols, amines or carbonxylic acids almost quantitatively under UV-light in neutral condition and the photoproduct showed high fluorescence intensity.
Assuntos
Cromonas/química , Cromonas/síntese química , Óxidos/química , Óxidos/síntese química , Compostos de Sulfidrila/química , Compostos de Sulfidrila/síntese química , Álcoois/síntese química , Álcoois/química , Álcoois/efeitos da radiação , Aminas/síntese química , Aminas/química , Aminas/efeitos da radiação , Ácidos Carboxílicos/síntese química , Ácidos Carboxílicos/química , Ácidos Carboxílicos/efeitos da radiação , Cromonas/efeitos da radiação , Ciclização , Estrutura Molecular , Óxidos/efeitos da radiação , Fotoquímica , Estereoisomerismo , Compostos de Sulfidrila/efeitos da radiação , Raios UltravioletaRESUMO
Epoxidation of imperatorin (1a) with m-chloroperbenzoic acid (mcpba) under the irradiation of gamma-ray gave a mixture of epoxide 3a and dioxofuran 4a. Whereas, alloimperatorin (1b) under the same condition obtained the epoxide 3b as a sole product. On the other hand, it was successfully epoxidized xanthotoxin (1c) with mcpba under the same condition as above. In addition, visnagin (2a) was epoxidized to give a mixture of epoxides 5a, 6a. While, khellin (2b) gave the epoxide 5b, no other products were observed.
