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

• Published in: ACS omega Vol. 7; no. 8; pp. 6944 - 6955
• Main Authors: 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
• Format: Journal Article
• Language: English
• Published: American Chemical Society 01-03-2022
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.1c06637

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 IC50 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.