Design and synthesis of novel 3-hydroxy-cyclobut-3-ene-1,2-dione derivatives as thyroid hormone receptor β (TR-β) selective ligands

https://doi.org/10.1016/j.bmcl.2008.06.038Get rights and content

Abstract

Design and synthesis of a novel 3-hydroxy-cyclobut-3-ene-1,2-dione derivatives are reported and their in vitro thyroid hormone receptor selectivity has been evaluated in the thyroid luciferase receptor assay. The 3-[3,5-dichloro-4-(4-hydroxy-3-isopropylphenoxy)-phenylamino]-4-hydroxy-cyclobut-3-ene-1,2-dione 21 has shown selectivity towards thyroid hormone receptor β.

Graphical abstract

Design and synthesis of a novel 3-hydroxy-cyclobut-3-ene-1,2-dione derivatives are reported and their thyroid hormone receptor selectivity has been evaluated. 3-[3,5-Dichloro-4-(4-hydroxy-3-isopropylphenoxy)-phenylamino]-4-hydroxy-cyclobut-3-ene-1,2-dione 21 has shown selectivity towards thyroid hormone receptor β.

  1. Download : Download full-size image

Section snippets

Acknowledgments

Authors are thankful to Dr. Brijesh Kumar Srivastava, Ms. Rina Soni, and Mr. Sidhartha S. Kar for their help in the preparation of the manuscript, management of the Zydus Group for encouragement and the analytical department for the support.

References and notes (35)

  • D.J. Mangelsdorf et al.

    Cell

    (1995)
  • D. Forresst et al.

    Thyroid

    (2000)
    K. Takeda et al.

    J. Clin. Endocrinol. Metab.

    (1992)
  • G.S. Boyd et al.

    J. Endocrinol.

    (1960)
  • Y. Wada et al.

    J. Mol. Endocrinol.

    (2000)
  • G. Chiellini et al.

    Chem. Biol.

    (1998)
  • J.J. Hangeland et al.

    Bioorg. Med. Chem. Lett.

    (2004)
  • R.L. Dow et al.

    Bioorg. Med. Chem. Lett.

    (2003)
  • B. Sandler et al.

    J. Biol. Chem.

    (2004)
  • A.S. Nascimento et al.

    J. Mol. Biol.

    (2006)
  • ArgusLab 4.0, Mark A. Thompson, Planaria Software LLC, Seattle. Available from:...
  • Thompson, M. A. Molecular docking using ArgusLab, an efficient shape-based search algorithm and the AScore scoring...
  • R.M. Evans

    Science

    (1988)
  • R.C. Riberio et al.

    Ann. Rev. Med.

    (1995)
  • M.A. Lazar

    Endocr. Rev.

    (1993)
  • J. Malm et al.

    Mini Rev. Med. Chem.

    (2007)
  • P.M. Yen

    Phys. Rev.

    (2001)
    H.L. Schwartz et al.

    J. Biol. Chem.

    (1992)
  • S.F. Engelken et al.

    Atherosclerosis

    (1981)
  • Cited by (0)

    ZRC communication # 241.

    View full text