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Synthesis and biological evaluation of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones as topoisomerase I inhibitors

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Chemistry of Heterocyclic Compounds Aims and scope

A series of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones were designed, synthesized, and evaluated as anticancer agents. Among them, two compounds demonstrated potent cytotoxicity and topoisomerase I inhibitory activity. In addition, their possible binding modes with topoisomerase I/DNA complex were proposed on the basis of molecular docking results.

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References

  1. Hsiang, Y. H.; Hertzberg, R.; Hecht, S.; Liu, L. F. J. Biol. Chem. 1985, 260, 14873.

    Article  CAS  PubMed  Google Scholar 

  2. Staker, B. L.; Hjerrild, K.; Feese, M. D.; Behnke, C. A.; Burgin, A. B.; Stewart, L. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 15387.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Liang, X.; Wu, Q.; Luan, S.; Yin, Z.; He, C.; Yin, L.; Zou, Y.; Yuan, Z.; Li, L.; Song, X.; He, M.; Lv, C.; Zhang, W. Eur. J. Med. Chem. 2019, 171, 129.

    Article  CAS  PubMed  Google Scholar 

  4. Pommier, Y. ACS Chem. Biol. 2013, 8, 82.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Hu, D.-X.; Tang, W.-L.; Zhang, Y.; Yang, H.; Wang, W.; Agama, K.; Pommier, Y.; An, L.-K. J. Med. Chem. 2021, 64, 7617.

    Article  CAS  PubMed  Google Scholar 

  6. Elbadawi, M. M.; Eldehna, W. M.; Wang, W.; Agama, K. K.; Pommier, Y.; Abe, M. Eur. J. Med. Chem. 2021, 215, 113261.

    Article  CAS  PubMed  Google Scholar 

  7. Martín-Encinas, E.; Rubiales, G.; Knudsen, B. R.; Palacios, F.; Alonso, C. Biorg. Med. Chem. 2021, 40, 116177.

    Article  Google Scholar 

  8. Kardile, R. A.; Sarkate, A. P.; Borude, A. S.; Mane, R. S.; Lokwani, D. K.; Tiwari, S. V.; Azad, R.; Burra, P. V. L. S.; Thopate, S. R. Bioorg. Chem. 2021, 115, 105174.

    Article  CAS  PubMed  Google Scholar 

  9. Wang, C.; Wang, Y.; Ma, H.; Zhu, Y.; Zhang, Y.; Miao, Z.; Wu, Y. Chem. Heterocycl. Compd. 2021, 57, 704. [Khim. Geterotsikl. Soedin. 2021, 57, 704.]

  10. Xiang, Y.; Li, H.; Wang, J.; Peng, X; Hu, C.; Luo, L. Med. Chem. Res. 2021, 30, 1512.

    Article  CAS  Google Scholar 

  11. Sharma, P. C.; Bansal, K. K.; Sharma, A.; Sharma, D.; Deep, A. Eur. J. Med. Chem. 2020, 188, 112016.

    Article  CAS  PubMed  Google Scholar 

  12. Chowdhury, A.; Patel, S.; Sharma, A.; Das, A.; Meshram, P.; Shard, A. Chem. Heterocycl. Compd. 2020, 56, 455. [Khim. Geterotsikl. Soedin. 2020, 56, 455.]

  13. Zhilitskaya, L. V.; Yarosh, N. О. Chem. Heterocycl. Compd. 2021, 57, 369. [Khim. Geterotsikl. Soedin. 2021, 57, 369.]

  14. Lin, H.; Schulz, M. J.; Xie, R.; Zeng, J.; Luengo, J. I.; Squire, M. D.; Tedesco, R.; Qu, J.; Erhard, K.; Mack, J. F.; Raha, K.; Plant, R.; Rominger, C. M.; Ariazi, J. L.; Sherk, C. S.; Schaber, M. D.; McSurdy-Freed, J.; Spengler, M. D.; Davis, C. B.; Hardwicke, M. A.; Rivero, R. A. ACS Med. Chem. Lett. 2012, 3, 524.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. O’Dowd, C. R.; Helm, M. D.; Rountree, J. S. S.; Flasz, J. T.; Arkoudis, E.; Miel, H.; Hewitt, P. R.; Jordan, L.; Barker, O.; Hughes, C.; Rozycka, E.; Cassidy, E.; McClelland, K.; Odrzywol, E.; Page, N.; Feutren-Burton, S.; Dvorkin, S.; Gavory, G.; Harrison, T. ACS Med. Chem. Lett. 2018, 9, 238.

    Article  PubMed  PubMed Central  Google Scholar 

  16. Ramtohul, Y. K.; Powell, D.; Leclerc, J.-P.; Leger, S.; Oballa, R.; Black, C.; Isabel, E.; Li, C. S.; Crane, S.; Robichaud, J.; Guay, J.; Guiral, S.; Zhang, L.; Huang, Z. Bioorg. Med. Chem. Lett. 2011, 21, 5692.

    Article  CAS  PubMed  Google Scholar 

  17. McCoull, W.; Barton, P.; Broo, A.; Brown, A. J. H.; Clarke, D. S.; Coope, G.; Davies, R. D. M.; Dossetter, A. G.; Kelly, E. E.; Knerr, L.; MacFaul, P.; Holmes, J. L.; Martin, N.; Moore, J. E.; Morgan, D.; Newton, C.; Österlund, K.; Robb, G. R.; Rosevere, E.; Selmi, N.; Stokes, S.; Svensson, T. S.; Ullah, V. B. K.; Williams, E. J. MedChemComm 2013, 4, 456.

    Article  CAS  Google Scholar 

  18. Li, Y.; Sun, L.; Yang, T.; Jiao, W.; Tang, J.; Huang, X.; Huang, Z.; Meng, Y.; Luo, L.; Wang, X.; Bian, X.; Zhang, F.; Wang, K.; Sun, Q. J. Med. Chem. 2019, 62, 159.

    Article  CAS  PubMed  Google Scholar 

  19. Jang, M.-Y.; Jonghe, S. D.; Segers, K.; Anné, J.; Herdewijn, P. Bioorg. Med. Chem. 2011, 19, 702.

    Article  CAS  PubMed  Google Scholar 

  20. Li, R.; Wang, H.; Wang, J.; Cheng, M. Bioorg. Med. Chem. Lett. 2020, 30, 126807.

    Article  CAS  PubMed  Google Scholar 

  21. Lin, R.; Johnson, S. G.; Connolly, P. J.; Wetter, S. K.; Binnun, E.; Hughes, T. V.; Murray, W. V.; Pandey, N. B.; Moreno-Mazza, S. J.; Adams, M.; Fuentes-Pesquera, A. R.; Middleton, S. A. Bioorg. Med. Chem. Lett. 2009, 19, 2333.

    Article  CAS  PubMed  Google Scholar 

  22. Karlström, S.; Nordvall, G.; Sohn, D.; Hettman, A.; Turek, D.; Åhlin, K.; Kers, A.; Claesson, M.; Slivo, C.; Lo-Alfredsson, Y.; Petersson, C.; Bessidskaia, G.; Svensson, P. H.; Rein, T.; Jerning, E.; Malmberg, Å.; Ahlgen, C.; Ray, C.; Vares, L.; Ivanov, V.; Johansson, R. J. Med. Chem. 2013, 56, 3177.

    Article  PubMed  Google Scholar 

  23. Luo, L.; Meng, L.; Sun, Q.; Ge, Z.; Li, R. RSC Adv. 2014, 4, 6845.

    Article  CAS  Google Scholar 

  24. Luo, L.; Meng, L.; Peng, Y.; Xing, Y.; Sun, Q.; Ge, Z.; Li, R. Eur. J. Org. Chem. 2015, 631.

  25. Peng, Y. Q.; Luo, L. C.; Gong, J.; Huang, J.; Sun, Q. Chin. Chem. Lett. 2015, 26, 1016.

    Article  CAS  Google Scholar 

  26. Wobig, D. Liebigs Ann. Chem. 1977, 400.

  27. Tian, X.; Song, L.; Li, E.; Wang, Q.; Yu, W.; Chang, J. RSC Adv. 2015, 5, 62194.

    Article  CAS  Google Scholar 

  28. Yang, L.; Shi, X.; Hu, B.-Q.; Wang, L.-X. Asian J. Org. Chem. 2016, 5, 494.

    CAS  Google Scholar 

  29. Johnson, S. G.; Connolly, P. J.; Murray, W. V. Tetrahedron Lett. 2006, 47, 4853.

    Article  CAS  Google Scholar 

  30. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Model. 2007, 13, 305.

    Article  CAS  PubMed  Google Scholar 

  31. Costa, P. J.; Nunes, R.; Vila-Viçosa, D. Expert Opin. Drug Discovery 2019, 14, 805.

    Article  CAS  Google Scholar 

  32. Wang, S.; Fang, K.; Dong, G.; Chen, S.; Liu, N.; Miao, Z.; Yao, J.; Li, J.; Zhang, W.; Sheng, C. J. Med. Chem. 2015, 58, 6678.

    Article  CAS  PubMed  Google Scholar 

  33. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. O’Boyle, N. M.; Banck, M.; James, C. A.; Morley, C.; Vandermeersch, T.; Hutchison, G. R. J. Cheminf. 2011, 3, 33.

    Article  Google Scholar 

  35. Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455.

    CAS  PubMed  PubMed Central  Google Scholar 

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This work was supported by the Scientific Research Project of Education Department of Hubei Province (D20192003).

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Authors and Affiliations

  1. Key Laboratory of Chinese Medicine Chemistry and Chinese Herbal Compound of Hubei Province, Hubei University of Chinese Medicine, Wuhan, 430065, China

    Laichun Luo, Qiang Wang, Yuanhang Xiang, Xiaozhi Peng & Chunling Hu

Authors
  1. Laichun Luo
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  2. Qiang Wang
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  3. Yuanhang Xiang
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  4. Xiaozhi Peng
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  5. Chunling Hu
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Corresponding author

Correspondence to Laichun Luo.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(12), 1220–1229

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Luo, L., Wang, Q., Xiang, Y. et al. Synthesis and biological evaluation of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones as topoisomerase I inhibitors. Chem Heterocycl Comp 57, 1220–1229 (2021). https://doi.org/10.1007/s10593-021-03046-7

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  • DOI: https://doi.org/10.1007/s10593-021-03046-7

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