Novel steroid mimics: synthesis of tri- and tetra-substituted oxamides and oxoamides

Ian L. Jones, Daniel J. Schofield, Robert R. Strevens, Peter N. Horton, Michael B. Hursthouse, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A series of dicarbonyl compds. have been designed and prepd. to mimic the rigid tetracyclic core of estradiol and dihydrotestosterone. Non-sym. tri- and tetra-substituted oxamides, e.g., I, were prepd. by the sequential addn. of primary and secondary amines to Ph cholorooxoacetate. Oxoamides, e.g., II, were prepd. via a Friedel-Crafts acylation/amide coupling protocol. Crystallog. data showed a good correlation between the structure of the dicarbonyl mimic and dihydrotestosterone complexed with the androgen receptor suggesting the mol. scaffolds may well prove versatile platforms for ligand design.
Original languageUndefined/Unknown
Pages (from-to)521-525
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number4
DOIs
Publication statusPublished - 2007

Keywords

  • tetra-substituted oxamides
  • Ph cholorooxoacetate
  • dihydrotestosterone
  • oxoamides

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