Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns |
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Authors: | Sachin B Baravkar Mahendra A Wagh Debasish Paul Manas Santra Gangadhar J Sanjayan |
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Institution: | 1. Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, Maharashtra, India;2. National Centre for Cell Science, Savitribai Phule Pune University, Ganeshkhind, Pune 411 007, Maharashtra, India |
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Abstract: | 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. |
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Keywords: | Smac mimetics Benzoxazinone AVPI tetrapeptide Sulfonamide MDA-MB-231 |
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