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Synthesis and characterization of new phenyl esters derived from 16-dehydropregnenolone acetate (16-DPA)

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Abstract

A series of new phenyl esters based on a 5,16-pregnadiene-20-one skeleton, namely 3β-benzoyloxy-5,16-pregnadiene-20-ones, which may be good inhibitors of 17α-hydroxylase and 5α-reductase enzyme or useful intermediates for producing steroidal drugs, were synthesized starting from diosgenin. The structures of the steroids were characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), and mass spectra.

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References

  1. X. Cui, B. Li, T. Liu, C. Li, Green Chem. 14, 668 (2012)

    Article  CAS  Google Scholar 

  2. M.V. Dansey, P.H. Di Chenna, A.S. Veleiro, Z. Krištofíková, H. Chodounska, A. Kasal, G. Burton, Eur. J. Med. Chem. 45, 3063 (2010)

    Article  CAS  Google Scholar 

  3. M.R. Angelastro, A.L. Marquart, P.M. Weintraub, C.A. Gates, M.E. Laughlin, T.R. Blohm, N.P. Peet, Bioorg. Med. Chem. Lett. 6, 97 (1996)

    Article  CAS  Google Scholar 

  4. M. Kumar, P. Rawat, M.F. Khan, A.K. Rawat, A.K. Srivastava, R. Maurya, Bioorg. Med. Chem. Lett. 21, 2232 (2011)

    Article  CAS  Google Scholar 

  5. P. Chowdhury, J.M. Borah, P. Goswami, A.M. Das, Steroids 76, 497 (2011)

    Article  CAS  Google Scholar 

  6. B.B. Shingate, B.G. Hazra, D.B. Salunke, V.S. Pore, F. Shirazi, M.V. Deshpande, Eur. J. Med. Chem. 46, 3681 (2011)

    Article  CAS  Google Scholar 

  7. Y.Z. Ling, J.Z. Li, Z. Kato, Bioorg. Med. Chem. 6, 1683 (1998)

    Article  CAS  Google Scholar 

  8. H. Li, Y. Song, X. Peng, Steroids 73, 488 (2008)

    Article  CAS  Google Scholar 

  9. H. Li, Y. Song, F. Ge, Acta Crystallogr. E 64, o783 (2008)

    Article  CAS  Google Scholar 

  10. J. Li, H. Li, Y. Li, Chem. Cent. J. 4, 18 (2010)

    Article  Google Scholar 

  11. J. Stoelwinder, W.J. van Zoest, A.M. van Leusen, J. Org. Chem. 57, 2249 (1992)

    Article  CAS  Google Scholar 

  12. K.E. Chapman, A. Odermatt, J. Steroid Biochem. Mol. Biol. 120, 67 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge the financial support of the project by Shanghai Natural Science Foundation (No. 06ZR14001).

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Correspondence to Hongqi Li.

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Li, H., Fang, J., Li, J. et al. Synthesis and characterization of new phenyl esters derived from 16-dehydropregnenolone acetate (16-DPA). Res Chem Intermed 39, 3887–3893 (2013). https://doi.org/10.1007/s11164-012-0890-5

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  • DOI: https://doi.org/10.1007/s11164-012-0890-5

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