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One-step Construction of Xanthone Scaffold Assisted by Microwave Irradiation to Optimize the Synthesis of DMXAA

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Abstract

An efficient and concise synthesis of 5,6-dimethylxanthenone-4-acetic acid(DMXAA) was developed. The overall yield of this 3-step procedure was 82%. The key reaction is the one-step construction of xanthone scaffold between 2,5-dibromo-3,4-dimethylbenzoic acid and 2-hydroxyphenyl-acetic acid assisted by microwave irradiation.

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References

  1. Pinto M. M., Sousa M. E., Nascimento M. S., Curr. Med. Chem., 2005, 12, 251

    Google Scholar 

  2. Adli A. D. F., Jahanban-Esfahlan R., Seidi K., Samandari-Rad S., Zarghami N., Chem. Biol. Drug Des., 2018, 91, 996

    Article  CAS  Google Scholar 

  3. Conlon J., Burdette D. L., Sharma S., Bhat N., Thompson M., Jiang Z., Rathinam V. A., Monks B., Jin T., Xiao T. S., Vogel S. N., J. Immunol., 2013, 190, 5216

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Rehman F., Rustin G., Exp. Opin. Inv. Drugs, 2008, 17, 1547

    Article  CAS  Google Scholar 

  5. Ching L. M., Cao Z., Kieda C., Zwain S., Jameson M. B., Baguley B. C., Br. J. Cancer, 2002, 86, 1937

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Tozer G. M., Kanthou C., Baguley B. C., Nat. Rev. Cancer, 2005, 5, 423

    Article  CAS  PubMed  Google Scholar 

  7. Pawel V., AACR-NCI-EORTC Meeting Proceedings, 2006, 16

    Google Scholar 

  8. Liu J., Zhang J., Wang H., Liu Z., Zhang C., Jiang Z., Chen H., Eur. J. Med. Chem., 2017, 133, 50

    Article  CAS  PubMed  Google Scholar 

  9. Li J., Jameson M. B., Baguley B. C., Pili R., Baker S. D., Clin. Cancer Res., 2008, 14, 2102

    Article  CAS  PubMed  Google Scholar 

  10. Rewcastle G. W., Atwell G. J., Zhuang L., Baguley B. C., Denny W. A., J. Med. Chem., 1991, 34, 217

    Article  CAS  PubMed  Google Scholar 

  11. Rewcastle G. W., Sutherland H. S., Weir C. A., Blackburn A. G., Denny W. A., Tetrahedron Lett., 2005, 46, 8719

    Article  CAS  Google Scholar 

  12. Atwell G. J., Yang S., Denny W. A., Eur. J. Med. Chem., 2002, 37, 825

    Article  CAS  PubMed  Google Scholar 

  13. Yang S., Denny W. A., Tetrahedron Lett., 2009, 50, 3945

    Article  CAS  Google Scholar 

  14. Abás S., Moens U., Escolano C., Tetrahedron Lett., 2017, 58, 2768

    Article  CAS  Google Scholar 

  15. Gawande M. B., Shelke S. N., Zboril R., Varma R. S., Acc. Chem. Res., 2014, 47, 1338

    Article  CAS  PubMed  Google Scholar 

  16. Gawande M. B., Bonifacio V. D. B., Luque R., Branco P. S., Varma R. S., Chem. Soc. Rev., 2013, 42, 5522

    Article  CAS  Google Scholar 

  17. Singh M. S., Chowdhury S., RSC Advances, 2012, 2, 4547

    Article  CAS  Google Scholar 

  18. Baig R. B. N., Varma R. S., Chem. Soc. Rev., 2012, 41, 1559

    Article  CAS  Google Scholar 

  19. Polshettiwar V., Varma R. S., Accounts Chem. Res., 2008, 41, 629

    Article  CAS  Google Scholar 

  20. Li J., Jin C., Su W., Heterocycles, 2011, 83, 855

    Article  CAS  Google Scholar 

  21. Ledochówski Z., Stefańska B., Roczniki Chem.: Ann. Soc. Chim. Polonorum, 1966, 40, 291

    Google Scholar 

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Correspondence to Heru Chen.

Additional information

Supported by the National Natural Science Foundation of China(No.81172982) and the Natural Science Foundation of Guangdong Province, China(No.2015A030311012).

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Jiang, Z., Liu, J., Zhou, F. et al. One-step Construction of Xanthone Scaffold Assisted by Microwave Irradiation to Optimize the Synthesis of DMXAA. Chem. Res. Chin. Univ. 34, 918–922 (2018). https://doi.org/10.1007/s40242-018-8148-4

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  • DOI: https://doi.org/10.1007/s40242-018-8148-4

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