Synthesis of new chromeno-annulated cis-fused pyrano[4,3-c]isoxazole derivatives via intramolecular nitrone cycloaddition and their cytotoxicity evaluation |
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| Authors: | Naveen Kumar Bejjanki Akkaladevi Venkatesham Jyothi Madda Nagaiah Kommu Sujitha Pombala C Ganesh Kumar Kothakonda Rajendra Prasad Jagadeesh Babu Nanubolu |
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| Institution: | 1. Division of Organic and Biomolecular Chemistry, CSIR – Indian Institute of Chemical Technology, Hyderabad 500 067, India;2. Center for Chemical Biology, CSIR – Indian Institute of Chemical Technology, Hyderabad 500 007, India;3. Center for Nuclear Magnetic Resonance, CSIR – Indian Institute of Chemical Technology, Hyderabad 500 007, India;4. Lab of X-ray Crystallography, CSIR – Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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| Abstract: | New cis-fused chromeno pyrano4,3-c]isoxazole derivatives have been synthesized by intramolecular 1,3]-cycloaddition of the nitrones generated in situ from hydroxylamine derivatives and 7-O-prenyl derivatives of 8-formyl-2,3-disubstituted chromenones using PEG-400 as a reaction medium under catalyst-free conditions good to excellent yields. The structures were established by spectroscopic data and further confirmed by X-ray diffraction analysis. The results showed that compounds 4b, 4c, 4d, 4e and 4k exhibit very potent antiproliferative activity against MDA-MB-231 breast cancer cells. Compounds 4a, 4c, 4e, 4i and 4k displayed potent inhibitory activity against human MCF-7 breast cancer cell lines. Compounds 4h and 4i exhibited significant anti-proliferative activity against human cervical cancer cell line, HeLa. While 4b, 4d and 4j were active against human lung cancer cell line, A549. In addition, Compound 4j was found to be the most promising against A549 (Lung cancer) with IC50 value of 0.194 μM. |
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| Keywords: | Nitrone cycloaddition Antiproliferative activity MCF-7 MDA-MB-231 breast cancer cell lines |
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