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

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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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  1. 1.

    Carson DA, Ribeiro JM (1993) Lancet 341:1251

  2. 2.

    Thun MJ, Henley SJ, Burns D, Jemal A, Shanks TG, Calle EE (2006) J Natl Cancer Inst 98:691

  3. 3.

    Suk OY, Young KH, Jin JS, Young PK, Young KS, Jung LH, Ok LE, Seok AK, Hoon KS (2009) Chin Sci Bull 54:387

  4. 4.

    Sohn EJ, Li H, Reidy K, Beers LF, Christensen BL, Lee SB (2010) Cancer Res 70:115

  5. 5.

    Zhang HZ, Kashibhatla S, Guastella J, Drew J, Tseng B, Cai SX (2003) Bioconjug Chem 14:458

  6. 6.

    Silva SRD, Bacchi MM, Bacchi CE, Oliveira DED (2007) Am J Clin Pathol 128:794

  7. 7.

    Thornberry NA (1998) Chem Biol 5:97

  8. 8.

    Syed FM, Hahn HS, Odley A, Guo Y, Vallejo JG, Lynch RA, Mann DL, Bolli R, Dorn GW (2005) Circ Res 96:1103

  9. 9.

    Mohr A, Zwacka RM (2007) Cell Biol Int 31:526

  10. 10.

    Marques CA, Keil U, Bonert A, Steiner B, Haass C, Muller WE, Eckert A (2003) J Biol Chem 278:28294

  11. 11.

    Salvesen GS, Dixit VM (1997) Cell 91:443

  12. 12.

    Cai SX, Zhang HZ, Guastella J, Drew J, Yang W, Weber E (2001) Bioorg Med Chem Lett 11:39

  13. 13.

    Jänicke RU (2008) Breast Can Res Treat 117:219

  14. 14.

    Jain AK, Veerasamy R, Vaidya A, Mourya V, Agrawal RK (2010) Med Chem Res 19:1191

  15. 15.

    Vaidya A, Jain S, Jain S, Jain AK, Agrawal RK (2014) J Pharm Sci Pharmacol 1:219

  16. 16.

    Yuan H, Pavel PA (2006) Bioorg Med Chem Lett 16:6267

  17. 17.

    Ravichandran V, Jain PK, Mourya VK, Agrawal RK (2007) Med Chem Res 16:342

  18. 18.

    Gupta SP, Babu MS, Garg R, Sowmya S (1998) J Enzyme Inhib 13:399

  19. 19.

    Duchowicz PR, Fernandez M, Carballero J, Castro EA, Fernandez FM (2006) Bioorg Med Chem 14:5876

  20. 20.

    Leonard JT, Roy K (2006) Bioorg Med Chem 14:1039

  21. 21.

    Ravichandran V, Agrawal RK (2007) Bioorg Med Chem Lett 17:2197

  22. 22.

    Prashanthakumar BR, Nanjan MJ (2010) Med Chem Res 19:1000

  23. 23.

    Prashanthakumar BR, Sankar G, Baig RBN, Chandrashekaran S (2009) Eur J Med Chem 44:4192

  24. 24.

    Vaidya A, Jain AK, Prashanthakumar BR, Kashaw SK, Agrawal RK (2011) J Enzyme Inhib Med Chem 26:854

  25. 25.

    Vaidya A, Jain S, Jain AK, Prashanthakumar BR, Kashaw SK, Agrawal RK (2015) Med Chem Res 24:383

  26. 26.

    V-Life Molecular Design Suite 3.0, VLife Sciences Technologies Pvt. Ltd; Baner Road: Pune, Maharashtra, India. Accessed Jan 2019

  27. 27.

    Nandi S, Bagchi MC (2010) Mol Divers 14:27

  28. 28.

    Vaidya A, Jain AK, Prashanthakumar BR, Sastry GN, Kashaw SK, Agrawal RK (2017) Arab J Chem 10:S3936

  29. 29.

    Zhang HZ, Kaisbhatla S, Kuemmerle J, Kemnitzer W, Mason KO, Qui L, Grundy CC, Tseng B, Drew J, Cai SX (2005) J Med Chem 48:5215

  30. 30.

    Kemnitzer W, Kuemmerle J, Zhang HZ, Kaisbhatla S, Tseng B, Drew J, Cai SX (2009) Bioorg Med Chem Lett 19:4410

  31. 31.

    Vaidya A, Jain S, Jain P, Jain P, Tiwari N, Jain R, Jain R, Jain AK, Agrawal RK (2016) Mini Rev Med Chem 16:825

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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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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 (2020).

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  • Oxadiazoles
  • CoMFA
  • CoMSIA
  • QSAR
  • [(SW) kNN MFA]
  • Synthesis
  • Anticancer activity