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Synthesis of 1,2,4-oxadiazole derivatives: anticancer and 3D QSAR studies

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Abstract

A 3D QSAR study was performed on 1,2,4-oxadiazole derivatives using the [(SW) kNN MFA], CoMFA, and CoMSIA techniques. On the basis of 3D QSAR outcomes, new molecules were designed by substituting different substituents. These designed compounds were synthesized and confirmed their synthesis by spectroscopic techniques. The synthesized compounds were screened for their anticancer activity against different cancer cell lines. Compound 2-[3-(pyridine-4-yl)-1,2,4-oxadiazol-5-yl]benzo[d]thiazole showed equipotent (IC50 = 4.96 μM) as 5-fluorouracil (IC50 = 3.2 μM) against colon (CaCo-2) cancer cell line, and compound [2-[3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl]benzo[d]thiazol-4-yl]methanol showed equipotent activity (IC50 = 0.35 μM) as compared to 5-fluorouracil (IC50 = 0.23 μM) against colorectal (DLD1) cancer cell line. Compound 2-[3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]benzo[d]thiazole was found to be 4–5 less potent (IC50 = 19.40 μM) as paclitaxel (IC50 = 4.10 μM) against breast (T47D) cancer cell line, and compound 4-[5-(benzo[d]thiazol-2-yl)-1,2,4-oxadiazol-3-yl]benzene-1,2-diol was found about 10 times less potent (IC50 = 15.7 μM) than mitomycin (IC50 = 1.50 μM) against prostate (PC-3) cancer cell line. These results disclose the discovery of new 1,2,4-oxadiazole-based anticancer drugs.

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Acknowledgements

We would like to thank Principal JSS College of Pharmacy, Ooty, India, for providing access to computational resources and for their valuable help during the modeling studies.

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Authors and Affiliations

  1. Pharmacy College, Saifai, Uttar Pradesh University of Medical Sciences, Saifai, Etawah, U.P., 206130, India

    Ankur Vaidya

  2. Sir MadanLal Institute of Pharmacy, Etawah, 206001, U.P., India

    Shweta Jain

  3. JSS College of Pharmacy, Mysore, 570015, India

    Br Prashantha Kumar

  4. Cancer Pharmacology Division, Indian Institute of Integrative Medicine (CSIR), Jammu, 180001, India

    Shashank K. Singh

  5. Department of Pharmaceutical Sciences, Dr. H.S. Gour University, Sagar, M.P., 470003, India

    Sushil Kumar Kashaw & Ram Kishore Agrawal

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  1. Ankur Vaidya
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  2. Shweta Jain
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  3. Br Prashantha Kumar
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  4. Shashank K. Singh
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Correspondence to Ankur Vaidya.

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Vaidya, A., Jain, S., Prashantha Kumar, B. et al. Synthesis of 1,2,4-oxadiazole derivatives: anticancer and 3D QSAR studies. Monatsh Chem 151, 385–395 (2020). https://doi.org/10.1007/s00706-020-02553-1

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  • DOI: https://doi.org/10.1007/s00706-020-02553-1

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