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Design, synthesis, and anticancer evaluation of new 1,3,4-oxadiazole thioether derivatives

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Abstract

A series of new 1,3,4-oxadiazole derivatives bearing the 2-positioned 2,5-dimethoxyphenyl substituent and 5-positioned organylsulfanyl moiety were designed and synthesized. Screening for anticancer activity against an array of human cancer cells revealed the superior activity of 2-(2,5-dimethoxyphenyl)-5-propylthio-1,3,4-oxadiazole. 2-(2,5-Dimethoxyphenyl)-5-butylthio-1,3,4-oxadiazole displayed excellent activity against breast cancer cell lines.

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References

  1. P. A. Mohite, D.H. Surve, M. Karpe, V. Kadam, World J. Pharm. Pharm. Sci., 2015, 4, 1386 [ISSN:2278-4357].

    Google Scholar 

  2. M. Tuncbilek, A. Kucukdumlu, E. B. Guven, D. Altiparmak, R. Cetin-Atalay, Bioorg. Med. Chem. Lett., 2018, 28, 235.

    Article  CAS  Google Scholar 

  3. https://www.who.int/en/news-room/fact-sheets/detail/cancer.

  4. J. J. Zhao, X. F. Wang, B. L. Li, R. L. Zhang, B. Li, Y. M. Liu, C. W. Li, J. B. Liu, B. Q. Chen, Bioorg. Med. Chem. Lett., 2016, 26, 4414.

    Article  CAS  Google Scholar 

  5. B. Kumar, A. Kumar, A. K. Beheraand, V. Raj, J. Cell Sci. Ther., 2016, 7, 1; DOI: https://doi.org/10.4172/2157-7013.1000233.

    Article  Google Scholar 

  6. M. F. Hassan, A. Rauf, A. Sherwani, M. Owais, Sci. Pharm., 2015, 83, 429.

    Article  CAS  Google Scholar 

  7. N. C. Desai, A. M. Dodiya, K. M. Rajpara, Y. M. Rupala, J. Saudi Chem. Soc., 2014, 18, 255.

    Article  Google Scholar 

  8. Q. Z. Zheng, X. M. Zhang, Y. Xu, K. Cheng, Q. C. Jiao, H. L. Zhu, Bioorg. Med. Chem., 2010, 18, 7836.

    Article  CAS  Google Scholar 

  9. S. Bajaj, V. Asati, J. Singh, P. P. Roy, Eur. J. Med. Chem., 2015, 97, 124.

    Article  CAS  Google Scholar 

  10. P. Li, L. Shi, M. N. Gao, X. Yang, W. Xue, L. H. Jin, D. Y. Hu, B. A. Song, Bioorg. Med. Chem. Lett., 2015, 25, 481.

    Article  CAS  Google Scholar 

  11. J. Sindhu, H. Singh, J. M. Khurana, C. Sharma, K. R. Aneja, Aust. J. Chem., 2013, 66, 710.

    Article  CAS  Google Scholar 

  12. F. Lo Monte, T. Kramer, J. Gu, M. Brodrecht, J. Pilakowski, A. Fuertes, J. M. Dominguez, B. Plotkin, H. Eldar-Finkelman, B. Schmidt, Eur. J. Med. Chem., 2013, 61, 26.

    Article  CAS  Google Scholar 

  13. Q. R. Du, D. D. Li, Y. Z. Pi, J. R. Li, J. Sun, F. Fang, W. Q. Zhong, H. B. Gong, H. L. Zhu, Bioorg. Med. Chem., 2013, 21, 2286.

    Article  CAS  Google Scholar 

  14. M. Madhu Sekhar, U. Nagarjuna, V. Padmavathi, A. Padmaja, N. V. Reddy, T. Vijaya, Eur. J. Med. Chem., 2018, 145, 1.

    Article  CAS  Google Scholar 

  15. K. H. Chikhalia, D. B. Vashi, M. J. Patel, J. Enzyme Inhib. Med. Chem., 2009, 24, 617.

    Article  CAS  Google Scholar 

  16. N. N. Farshori, M. R. Banday, A. Ahmad, A. U. Khan, A. Rauf, Bioorg. Med. Chem. Lett., 2010, 20, 1933.

    Article  CAS  Google Scholar 

  17. Y. Chen, X. Xu, X. Liu, M. Yu, B. F. Liu, G. Zhang, PLoS One, 2012, 7, e35186.

    Article  CAS  Google Scholar 

  18. J. F. Tang, X. H. Lv, X. L. Wang, J. Sun, Y. B. Zhang, Y. S. Yang, H. B. Gong, H. L. Zhu, Bioorg. Med. Chem., 2012, 20, 4226.

    Article  CAS  Google Scholar 

  19. I. M. Yonova, C. A. Osborne, N. S. Morrissette, E. R. Jarvo, J. Org. Chem., 2014, 79, 1947.

    Article  CAS  Google Scholar 

  20. F. Zhang, X. L. Wang, J. Shi, S. F. Wang, Y. Yin, Y. S. Yang, W. M. Zhang, H. L. Zhu, Bioorg. Med. Chem., 2014, 22, 468.

    Article  CAS  Google Scholar 

  21. N. Polkam, P. Rayam, J. S. Anireddy, S. Yennam, H. S. Anantaraju, S. Dharmarajan, Y. Perumal, S. S. Kotapalli, R. Ummanni, S. Balasubramanian, Bioorg. Med. Chem. Lett., 2015, 25, 1398.

    Article  CAS  Google Scholar 

  22. N. Polkam, V. R. Ramaswamy, P. Rayam, T. R. Allaka, H. S. Anantaraju, S. Dharmarajan, Y. Perumal, D. Gandamalla, N. R. Yellu, S. Balasubramanian, J. S. Anireddy, Bioorg. Med. Chem. Lett., 2016, 26, 2562.

    Article  CAS  Google Scholar 

  23. T. R. Allaka, N. Polkam, P. Rayam, J. Sridhara, N. S. Garikapati, S. S. Kotapalli, R. Ummanni, J. S. Anireddy, Med. Chem. Res., 2016, 25, 977.

    Article  CAS  Google Scholar 

  24. N. Polkam, B. Kummari, P. Rayam, U. Brahma, V. G. M. Naidu, S. Balasubramanian, J. S. Anireddy, Chemistry Select, 2017, 2, 5492.

    CAS  Google Scholar 

  25. P. Rayam, N. Polkam, N. Kuntala, V. Banothu, H. S. Anantaraju, Y. Perumal, S. Balasubramanian, J. S. Anireddy, J. Heterocycl. Chem., 2020, 57, 1.

    Article  Google Scholar 

  26. F. Macaev, Z. Ribkovskaia, S. Pogrebnoi, V. Boldescu, G. Rusu, N. Shvets, A. Dimoglo, A. Geronikaki, R. Reynolds, Bioorg. Med. Chem., 2011, 19, 6792.

    Article  CAS  Google Scholar 

  27. F. Rahim, F. Malik, H. Ullah, A. Wadood, F. Khan, M. T. Javid, M. Taha, W. Rehman, A. Ur Rehman, K. M. Khan, Bioorg. Chem., 2015, 60, 42.

    Article  CAS  Google Scholar 

  28. V. G. M. Naidu, U. M. Bandari, A. K. Giddam, K. R. D. Babu, J. Ding, K. S. Babu, B. Ramesh, R. R. Pragada, P. Gopalakrishnakone, Asian Pac. J. Trop. Med., 2013, 6, 337.

    Article  CAS  Google Scholar 

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Correspondence to J. S. Anireddy.

Additional information

N. Polkam is thankful to University Grants Commission (UGC), New Delhi, Government of India for financial assistance in the form of a senior research fellowship. Authors N. Polkam and J. S. Anireddy are thankful to TEQIP-II for aiding improved laboratory facilities.

This work does not involve human participants and animal subjects.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 580–584, March, 2021.

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Polkam, N., Malthum, S., Anireddy, J.S. et al. Design, synthesis, and anticancer evaluation of new 1,3,4-oxadiazole thioether derivatives. Russ Chem Bull 70, 580–584 (2021). https://doi.org/10.1007/s11172-021-3128-0

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  • DOI: https://doi.org/10.1007/s11172-021-3128-0

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