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Gold(I)-Catalyzed Synthesis of 4H-Benzo[d][1,3]oxazines and Biological Evaluation of Activity in Breast Cancer Cells

[Image: see text] The first gold(I)-catalyzed cycloisomerization procedure applied to the synthesis of substituted 4H-benzo[d][1,3]oxazines has been developed starting from N-(2-alkynyl)aryl benzamides. The chemoselective oxygen cyclization via the 6-exo-dig pathway yielded the observed heterocycles...

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Detalles Bibliográficos
Autores principales: Segura-Quezada, Luis A., Torres-Carbajal, Karina R., Mali, Narendra, Patil, Dipak B., Luna-Chagolla, Mauricio, Ortiz-Alvarado, Rafael, Tapia-Juárez, Melissa, Fraire-Soto, Ixamail, Araujo-Huitrado, Jorge Gustavo, Granados-López, Angelica Judith, Gutiérrez-Hernández, Rosalinda, Reyes-Estrada, Claudia Araceli, López-Hernández, Yamilé, López, Jesús Adrián, Chacón-García, Luis, Solorio-Alvarado, César R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8892638/
https://www.ncbi.nlm.nih.gov/pubmed/35252686
http://dx.doi.org/10.1021/acsomega.1c06637
Descripción
Sumario:[Image: see text] The first gold(I)-catalyzed cycloisomerization procedure applied to the synthesis of substituted 4H-benzo[d][1,3]oxazines has been developed starting from N-(2-alkynyl)aryl benzamides. The chemoselective oxygen cyclization via the 6-exo-dig pathway yielded the observed heterocycles in modest to good chemical yields under very mild reaction conditions. The obtained oxazines were assayed on the breast cancer (BC)-derived cell lines MCF-7 and HCC1954 with differential biological activity. The newly synthesized 4H-benzo[d][1,3]oxazine compounds showed several degrees of cell proliferation inhibition with a remarkable effect for those compounds having a substituted aryl at C-2 of the molecules. The 4H-benzo[d][1,3]oxazines showed an IC(50) ranking from 3.1 to 95 μM in MCF-7 and HCC1954 cells. These compounds represent potential drug candidates for BC treatment. However, additional assays are needed to elucidate their complete effect over the cellular and molecular hallmarks of cancer.