| Author | Diaz-Muñoz, Gaspar | |
| Author | Miranda, Izabel Luzia | |
| Author | Sartori, Suélen Karine | |
| Author | Dias, Gabriel Nunes de Souza | |
| Author | Kohlhoff, Markus | |
| Author | Purgato, Gislaine Aparecida | |
| Author | Diaz, Marisa Alves Nogueira | |
| Access date | 2022-08-18T18:39:20Z | |
| Available date | 2022-08-18T18:39:20Z | |
| Document date | 2018 | |
| Citation | DIAZ-MUÑOZ, Gaspar et al. Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity. J. Braz. Chem. Soc., v. 29, n. 12, p. 2646-2656, 2018. https://doi.org/10.21577/0103-5053.20180145 | pt_BR |
| ISSN | 0103-5053 | pt_BR |
| URI | https://www.arca.fiocruz.br/handle/icict/54724 | |
| Sponsorship | FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE MINAS GERAIS | pt_BR |
| Language | eng | pt_BR |
| Publisher | Sociedade Brasileira de Química | pt_BR |
| Rights | open access | pt_BR |
| Title | Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity | pt_BR |
| Type | Article | pt_BR |
| DOI | 10.21577/0103-5053.20180145 | |
| Abstract | A novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (+/-)-galipinine, (+/-)-cuspareine, (t)-galipeine and (+/-)-angustureine, and the derivative (+/-)-11-methoxy-5,6.6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1.2-a]naphilialene-12-ol from their respective Wittig adducts in moderate and high yields. The solvolytic N-methylation reaction was shown to be catalyzed by Pt-0, generated in situ by reduction of PtO2. The evaluation of biofilm inhibition and antibacterial activity of the compounds against Staphylococcus aureus strains isolated from cows with mastitis revealed that the alkaloid derivative is a promising candidate for an antibiotic drug. | pt_BR |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil | pt_BR |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil | pt_BR |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil | pt_BR |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Aquacultura. Belo Horizonte, MG, Brazil | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto René Rachou. Química de Produtos Naturais Bioativos. Belo Horizonte, MG, Brazil | pt_BR |
| Affilliation | Universidade Federal de Viçosa. Departamento de Bioquímica e Biologia Molecular. Viçosa, MG, Brazil | pt_BR |
| Affilliation | Universidade Federal de Viçosa. Departamento de Bioquímica e Biologia Molecular. Viçosa, MG, Brazil | pt_BR |
| Subject | tetrahydroquinoline alkaloids | pt_BR |
| Subject | Wittig reaction | pt_BR |
| Subject | solvolytic N-methylation | pt_BR |
| Subject | antibacterial activity | pt_BR |
