Elsevier

Tetrahedron Letters

Volume 32, Issue 18, 29 April 1991, Pages 2061-2064
Tetrahedron Letters

Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen)

https://doi.org/10.1016/S0040-4039(00)78908-8Get rights and content

Abstract

A naturally occurring benzofuran, namely 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde was isolated from the roots of S. miltiorrhiza Bunge “Danshen”. Its structure was established by means of spectroscopic methods as well as by a total synthesis. Both the natural and the synthetic compounds showed a high potency (IC50 = 17 nM and 10 nM, respectively) in the bovine adenosine A1 radioligand binding.

The title compound was isolated from the root of S. miltiorrhiza Bunge (Danshen) and its structure was established by spectroscopic methods as well as by a total synthesis.

References (12)

  • F.G. Schreiber et al.

    J. Chem. Soc., Perkin Trans. 1

    (1976)
    C.E. Castro et al.

    J. Org. Chem.

    (1966)
  • H.M. Chang et al.

    J. Chem. Res. (S)

    (1990)
    H.M. Chang et al.

    J. Org. Chem.

    (1990)
  • W.Z. Chen

    Acta Pharm. Sinica

    (1984)
    C.W. Liu
  • A.N. Drury et al.

    J. Physiol.

    (1929)
    R.M. Berne

    Am. J. Physiol.

    (1963)
    J.W. Daly

    J. Med. Chem.

    (1982)
  • W.T. Cheung et al.

    Biochem. Pharmacol.

    (1987)
There are more references available in the full text version of this article.

Cited by (85)

  • Danshen: a phytochemical and pharmacological overview

    2019, Chinese Journal of Natural Medicines
  • An alternate method for the synthesis of 2-aryl/alkyl-5-bromo-7-methoxy benzofurans; application to the synthesis of Egonol, Homoegonol, and analogs via Heck reaction

    2016, Tetrahedron
    Citation Excerpt :

    These compounds were found to exhibit broad range of biological activities including cytotoxicity, antimicrobial, fungicidal, anti-inflammatory, anti-asthma, and anti-oxidant properties.8–11 Lignans like (IV) possess formyl group at C-3 position along with the 3-hydroxypropyl side chain at C-5 position has also been reported for its adenosine A1 receptor activities.12 In view of this broad spectrum of biological activity and therapeutic applications associated with these compounds, number of approaches has been developed for the efficient synthesis of their basic skeleton.13

View all citing articles on Scopus
1

Correspondence concerning the isolation and bioassays should be addressed to C.M.L. All other correspondence should be addressed to H.N.C.W.

View full text