Synthesis of Novel 1,2,3-Triazole-Dihyropyrimidinone Hybrids using Multicomponent 1,3-Dipolar Cycloaddition(Click)-Biginelli Reactions

• Autor(a) principal: Carreiro, Elisabete
• Data de Publicação: 2020
• Outros Autores: Burke, Anthony, Sena, Ana Margarida, Padrón, José, Puerta, Adrián
• Tipo de documento: Artigo
• Idioma: por
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10174/28376; https://doi.org/10.1055/s-0039-1690781
• topic: 1,2,3-triazole; Dihydropyrimidinone

Inthiswork,21novel(1,4-disubstituted1,2,3-triazole)-dihy- dropyrimidinone (1,2,3-trzl-DHPM) type hybrids were synthesized and characterized. These were divided into two types: hybrids A (5 in total) containing the dihydropyrimidinone heterocyclic ring decorated with a 1,4-disubstituted 1,2,3-triazole in the C-5 position [these compounds were accessed by a multicomponent copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) (or click)–Biginelli reactions with satisfactory yields (39–57%)] and hybrids B (16 in total) containing two 1,2,3-tri- azole units in the C-5 and C-6 methyl position of the DHPM. Hybrids B were synthesized via functionalization of the C-6 methyl group of hy- brids A, a multistep sequence of reactions was used that included bro- mination, azidation, and a CuAAC. Hybrids B were obtained in very good to excellent yields (up to 99%). Some hybrids A and B were evalu- ated for their antiproliferative activity against different cancer cell lines that included A549 and SW1573 (non-small-cell lung), HBL-100 and T-47D (breast), HeLa (cervix) and WiDr (colon). Three of these hybrids were potent cell proliferation inhibitors of non-small-cell lung cancer, cervix cancer, breast cancer, and colon cancer.