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Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns
Baravkar, S. B., Wagh, M. A., Paul, D., Santra, M., & Sanjayan, G. J. (2018). Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns. Tetrahedron Letters, 59(38), 3473-3476. https://doi.org/10.1016/j.tetlet.2018.08.016
Herein, we report synthesis and in vitro anticancer activity of conformationally constrained Smac mimetics containing reverse turn inducing motifs "Ant-Pro" and "sAnt-Pro". The synthesis of Smac analogs with diverse hydrophobic groups at the C-terminus was carried out using solution phase peptide synthesis. The synthesis of Ant-Pro containing analogs 3a-j was carried out by ring opening of benzoxazinones 7a-c, whereas, their sulfonamide counterparts 4a-h were synthesized by using routine acid-amine coupling reaction. In vitro anticancer studies against breast cancer cell line MDA-MB-231 revealed that some of the new analogs had better anticancer activity than the standard AVPI Smac tetrapeptide. (C) 2018 Published by Elsevier Ltd.