Potent, non-peptidic oxytocin receptor antagonists from a natural source

https://doi.org/10.1016/S0960-894X(01)80905-7Get rights and content

Abstract

Penicillide, a previously described natural product, and several related compounds have been discovered to be antagonists of the peptide hormone oxytocin. A few simple derivatives of the compound were isolated and/or synthesized and its absolute stereochemistry was determined.

Penicillide and related compounds have been discovered to be antagonists of the peptide hormone oxytocin. Several derivatives of the natural product were prepared and its absolute stereochemistry was determined.

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References (10)

  • B.A. Morgan et al.
  • T. Sassa et al.

    Tetrahedron Lett.

    (1974)
  • M.A. Goetz et al.

    J. Antibiot.

    (1985)
  • J.A. Pritchard et al.
  • D.J. Pettibone et al.

    Endocrinology

    (1989)
There are more references available in the full text version of this article.

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