RESUMO
Paeonol is a broadly studied natural product due to its many biological activities. Using a methodology previously employed by our research group, 11 derivatives of paeonol were synthesized (seven of them are unpublished compounds), including four ethers and seven benzofurans. Additionally, we determined the crystal structure of one of these ether derivatives (1 a) and of five benzofuran derivatives (2 a, 2 b, 2 c, 2 f and 2 g) by single crystal X-ray diffraction. To continue studying the cytotoxicity of this natural product and its derivatives, all compounds were tested against two cancer cell lines, HCT116 and MCF-7. Compounds 2 b, 2 e, and 2 g were considered active against the colorectal adenocarcinoma cells HCT116 (Growth inhibition >60 %). Compound 2 e showed an IC50 of 0.2â µM and was selected for further analysis, results reinforce its anticancer potential.
Assuntos
Acetofenonas , Antineoplásicos , Benzofuranos , Proliferação de Células , Ensaios de Seleção de Medicamentos Antitumorais , Éteres , Humanos , Benzofuranos/química , Benzofuranos/farmacologia , Benzofuranos/síntese química , Acetofenonas/química , Acetofenonas/farmacologia , Acetofenonas/síntese química , Antineoplásicos/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Éteres/química , Éteres/farmacologia , Éteres/síntese química , Relação Estrutura-Atividade , Proliferação de Células/efeitos dos fármacos , Estrutura Molecular , Relação Dose-Resposta a Droga , Cristalografia por Raios X , Linhagem Celular Tumoral , Células HCT116 , Células MCF-7RESUMO
Herein, we report a solvent- and metal-free methodology for the alkoxy-chalcogenylation of styrenes, using molecular iodine as a catalyst, DMSO as a stoichiometric oxidant, and different nucleophiles under microwave irradiation. This eco-friendly approach afforded the desired products in good to excellent yields in only 10 min. In addition, using the same protocol, we carried out the cyclization reaction of relevant molecules, such as lapachol derivatives.
Assuntos
Dimetil Sulfóxido/química , Éteres/síntese química , Iodo/química , Estirenos/química , Catálise , Ciclização , Éteres/química , Micro-Ondas , Estrutura Molecular , Oxidantes/químicaRESUMO
Herein, it is provided an efficient and one-pot procedure for the synthesis of novel and diversely substituted γ-aminoethers in good yields through a four-component process by treatment of benzylamines with polyformaldehyde and activated alkenes in aliphatic alcohols acting both as solvent and as etherificant agents. Reactions proceeded via a Mannich-type reaction, where the formation of iminium ions and aminals was identified as the key intermediates to obtain the target products.
Assuntos
Benzilaminas/química , Éteres/síntese química , Éteres/química , Estrutura Molecular , EstereoisomerismoRESUMO
Allyl 1-naphthyl ethers are useful compounds for different purposes, but reported methods to synthesize them require long reaction times. In this work, we have obtained allyl 1-naphthyl ether in good yield using ultrasonic-assisted methodology in a 1-h reaction. A central composite design was used to obtain a statistical model and a response surface (p<0.05; R(2)=0.970; R(2)(adj)=0.949; R(2)(pred)=0.818) that can predict the optimal conditions to maximize the yield, validated experimentally.
Assuntos
Éteres/química , Éteres/síntese química , Ultrassom , Naftóis/química , Propriedades de SuperfícieRESUMO
A practical and efficient procedure for the enantioselective synthesis of mexiletine analogues with use of 10% of spiroborate ester 6 as chirality transfer agent is presented. A variety of mexiletine analogues were prepared in good yield with excellent enantioselectivities (91-97% ee) from readily available starting materials. The developed methodology was also successfully applied for the synthesis of novel beta-amino ethers containing thiophenyl and pyridyl fragments.