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Design, synthesis, and evaluation of the anticancer properties of a novel series of carboxamides, sulfonamides, ureas, and thioureas derived from 1,2,4-oxadiazol-3-ylmethyl-piperazin-1-yl substituted with pyrazolo[1,5-a]pyrimidine derivatives

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Abstract

A series of novel carboxamides, sulfonamides, ureas, and thioureas derived from 1,2,4-oxadiazol-3-ylmethyl-piperazin-1-yl substituted with pyrazolo[1,5-a]pyrimidine analog were designed and synthesized. The newly synthesized compounds were characterized by 1H NMR, 13C NMR, ESI–MS, and IR and were tested for their in vitro antiproliferative activity by MTT assay. Out of these twenty derivatives, five compounds showed good anticancer activity against HeLa cell line. These are superior with less than 10 µg/cm3 of IC 50 when compared to the marketed anticancer drug paclitaxel with 30 µg/cm3 of IC 50 against Hela cell line.

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Acknowledgments

We would like to thank the Management Team at Anthem Biosciences Pvt. Ltd., Bangalore, India, for their valuable support and allocation of proper resources for the completion of this work. We would also like to thank the Analytical Chemistry Team at the Department of Analytical chemistry, Anthem Biosciences, Bangalore, India, for carrying out all the analytical work described in this study. Also, we would like to thank the Molecular Biology Team at the Maratha Mandal Institute of Technology, Belagavi, Karnataka, India, for conducting the anti-proliferative studies by MTT assay.

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Authors and Affiliations

  1. Anthem Biosciences Pvt. Ltd., # 49, Bommasandra Industrial Area, Bommasandra, Bangalore, 560 099, Karnataka, India

    A. K. Ajeesh Kumar, Kanya B. Nair & Ganesh Sambasivam

  2. Department of PG Studies and Research in Industrial Chemistry, School of Chemical Sciences, Kuvempu University, Jnana Sahyadri, Shankaraghatta, Shimoga, 577 451, Karnataka, India

    Yadav D. Bodke

  3. Department of Microbiology, Maratha Mandal’s NGH Institute of Dental Sciences and Research Centre, Belgaum, 590 010, Karnataka, India

    Kishore G. Bhat

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  1. A. K. Ajeesh Kumar
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Correspondence to A. K. Ajeesh Kumar.

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Ajeesh Kumar, A.K., Nair, K.B., Bodke, Y.D. et al. Design, synthesis, and evaluation of the anticancer properties of a novel series of carboxamides, sulfonamides, ureas, and thioureas derived from 1,2,4-oxadiazol-3-ylmethyl-piperazin-1-yl substituted with pyrazolo[1,5-a]pyrimidine derivatives. Monatsh Chem 147, 2221–2234 (2016). https://doi.org/10.1007/s00706-016-1723-9

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