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Lewis base-catalyzed synthesis of highly functionalized spirooxindole-pyranopyrazoles and their in vitro anticancer studies

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Abstract

Herein, the one-step, multi-component reaction (MCR) of a series of spirooxindole-pyranopyrazole derivatives (5a-g), via a Knoevenagel condensation and Michael addition cascade, under mild and green reaction conditions, is reported. The newly synthesized derivatives were screened for in vitro anti-cancer activity against 60 human cancer cell lines at the National Cancer Institute (NCI), USA. We found that compounds 5c, 5d, and 5g showed good activity against the HOP-92 (lung cancer), UO-31 (renal cancer), KM-12, SW-620 (colon cancer), and HS578T (breast cancer) cell lines. Compound 5c showed 43.19 and 21.18% growth inhibition at 10 μM for HOP-92 and UO-31 cell lines, respectively, while compound 5g showed 82.02% growth inhibition for the KM12 cell line at the same concentration. Therefore, the compound 5g could be further derivatized as a futuristic lead molecule for colorectal cancer.

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Acknowledgements

The authors gratefully acknowledge the R&D wing of Integral University, Lucknow, for providing communication number IU/R&D/2022-MCN0001718. Dr. Amani salem almalki and Fatmah Ali Alasmary are thankful to Support through Researchers Supporting Project number (RSP2023R259), King Saud University, Riyadh, Saudi Arabia.

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Authors and Affiliations

  1. Department of Chemistry, Integral University, Lucknow, 226026, U.P., India

    Mohd Asif, Abdul Rahman Khan & Malik Nasibullah

  2. UofL Health-Brown Cancer Center and Department of Medicine, University of Louisville, Louisville, KY40202, USA

    Farrukh Aqil

  3. Chemistry Department, College of Science, King Saud University, Riyadh, 11451, Saudi Arabia

    Fatmah Ali Alasmary & Amani salem almalki

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MA performed this research work under the direction of MN with the financial support of ASA and FAA under the Researchers Supporting Project number (RSP2023R259) at King Saud University, Riyadh, Saudi Arabia.

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Asif, M., Aqil, F., Alasmary, F.A. et al. Lewis base-catalyzed synthesis of highly functionalized spirooxindole-pyranopyrazoles and their in vitro anticancer studies. Med Chem Res 32, 1001–1015 (2023). https://doi.org/10.1007/s00044-023-03053-7

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