Synthesis of new steroidal derivatives by the reaction of steroid-amino acid conjugates with N,N′-dicyclohexyl-carbodiimide. Unusual formation of steroidal imide derivatives

Eszter Takács, Zoltán Berente, Viktor Háda, Sándor Mahó, László Kollár, Rita Skoda-Földes

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Several new steroid derivatives have been synthesised by the reaction of steroid-amino acid conjugates with N,N′-dicyclohexyl-carbodiimide. Selectivity of the reaction was found to depend greatly on the properties of the amino acid moiety. While the reaction of the glycine derivative led to the corresponding 5(4H)-oxazolone, an unusual imide formation together with an N-acylurea side product was observed in the case of conjugates of l-alanine, l-phenylalanine and l-methionine. The structures of the new products, steroidal imide and N-acylurea derivatives, were determined by various spectroscopic methods.

Original languageEnglish
Pages (from-to)4659-4663
Number of pages5
JournalTetrahedron
Volume65
Issue number24
DOIs
Publication statusPublished - Jun 13 2009

Keywords

  • Amino acids
  • DCC
  • Imides
  • Steroids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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