Discovery of a new class of 16-membered (2Z,11Z)-3,11-di(aryl/naphthyl)-1,13-dioxa-5,9-dithia-2,12-diazacyclohexadeca-2,11-dienes as anti-tumor agents
| Autor: | P. Md. Khaja Mohinuddin, D. Vijaya Raghava Prasad, Ranjeet Singh Mahla, Himanshu Kumar, Mohan Reddy Bodireddy, G. Trivikram Reddy, N. C. Gangi Reddy |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Stereochemistry General Chemical Engineering Aryl Cell migration General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry In vitro 0104 chemical sciences chemistry.chemical_compound Downregulation and upregulation Cell culture Cancer cell Cytotoxic T cell Triple-negative breast cancer |
| Zdroj: | RSC Advances. 6:75651-75663 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c6ra15140j |
| Popis: | A series of new 16-membered small macrocyclic compounds, (2Z,11Z)-3,11-di(aryl/naphthyl)-1,13-dioxa-5,9-dithia-2,12-diazacyclohexadeca-2,11-dienes (1a–k) were designed and developed by a simple and practical synthetic route from readily available substrates using simple organic transformations. Evaluation of in vitro anti-tumor activities on human triple negative breast cancer cells MDAMB-231 cell lines reveal that the macrocycles, 1a, 1f, 1g, 1i and 1k are promising anti-tumor compounds as evidenced from inhibition of cell migration and proliferation, upregulation of anti-tumor genes p53, MDA7 and TRAIL. The anti-proliferative effect of macrocycles is specific to cancer cells but no cytotoxic effect on normal breast epithelial cells has been observed (MCF10A). The developed synthetic route is free from metals, protecting groups and air-free techniques. The structure of macrocycle (1e) is confirmed by single crystal XRD studies. |
| Databáze: | OpenAIRE |
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