Reação de Mannich Com Enaminonaftoquinonas: Nova Metodologia Para a Síntese de Poliaminas Com Potencial Atividade Antiproliferativa de Células Cancerígenas

• Ano de defesa: 2024
• Autor(a) principal: Cunha, Vinícius Souza
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal do Espírito Santo; BR; Mestrado em Química; Centro de Ciências Exatas; UFES; Programa de Pós-Graduação em Química
• Palavras-chave em Português: Reação de Mannich; enaminonaftoquinonas; reagentes eletrofílicos; subject.br-rjbn; Área(s) do conhecimento do documento (Tabela CNPq)
• Link de acesso: http://repositorio.ufes.br/handle/10/17425

The Mannich reaction is the condensation of a substrate containing an activated hydrogen, an unenolizable carbonyl compound with a primary or secondary amine, or ammonium chloride. Modern methodologies of the Mannich reaction use pre-formed electrophilic reagents, ensuring a higher concentration of the electrophile in the reaction medium and minimizing reaction disadvantages. Enaminonaphthoquinones are compounds of the naphthoquinone class functionalized with an amino group at C2. The objective was to develop a series of novel Mannich bases using enaminonaphthoquinones and electrophilic reagents. All enaminonaphthoquinones were prepared by nucleophilic substitution or azide addition. Through methodological development, the need for highly electrophilic substrates was verified. For this purpose, pre-synthesized pyrrolidinemethyleneammonium chloride and Eschenmoser salt were used. Mannich bases 131, 132, 133, 136, 137, 138, and 139 are unpublished in the literature and were prepared with yields ranging from 10 to 88%. The structures were elucidated by infrared, 1H NMR, 13C NMR, and GC-MS. Regarding in situ cytotoxic assays, it is concluded that the compounds have greater antiproliferative activity against cancer cells than enaminonaphthoquinones for the following cancer cell lines: HCT-116 (human colon carcinoma) and PC-3 (human prostate carcinoma).