Reagents for Photoaffinity Labeling of Estrogen Binding Proteins. Synthesis of Some Azide and Diazo Derivatives of Estradiol, Estrone, and Hexestrol

John A. Katzenellenbogen, Harvey N. Myers, Howard J. Johnson

Research output: Contribution to journalArticlepeer-review

Abstract

Fourteen estrogen derivatives bearing a photosensitive functional group have been synthesized for use as photo-affinity labels for estrogen binding proteins: diazoacetate derivatives of 17β-estradiol and estrone, 16-diazoestrone, and 3-diazo-2-ketopropyl ether and ortho azide derivatives of estradiol, estrone, and hexestrol. All of these compounds are reasonably stable and easily purifiable. Attempts to introduce a diazo function at B-ring positions 6 and 7 of the estrogens have been unsuccessful: the 6-diazo derivative is thermally labile and the 6-keto-7-diazo derivative fails to form. This is presumably due to the hindrance at position 7, as the corresponding position (2) in 7-hydroxy-1-tetralone is easily functionalized.

Original languageEnglish (US)
Pages (from-to)3525-3533
Number of pages9
JournalJournal of Organic Chemistry
Volume38
Issue number20
DOIs
StatePublished - Oct 1 1973

ASJC Scopus subject areas

  • Organic Chemistry

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