Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Hormone Molecular Biology and Clinical Investigation

Editor-in-Chief: Chetrite, Gérard S.

Editorial Board Member: Alexis, Michael N. / Baniahmad, Aria / Beato, Miguel / Bouillon, Roger / Brodie, Angela / Carruba, Giuseppe / Chen, Shiuan / Cidlowski, John A. / Clarke, Robert / Coelingh Bennink, Herjan J.T. / Darbre, Philippa D. / Drouin, Jacques / Dufau, Maria L. / Edwards, Dean P. / Falany, Charles N. / Fernandez-Perez, Leandro / Ferroud, Clotilde / Feve, Bruno / Flores-Morales, Amilcar / Foster, Michelle T. / Garcia-Segura, Luis M. / Gastaldelli, Amalia / Gee, Julia M.W. / Genazzani, Andrea R. / Greene, Geoffrey L. / Groner, Bernd / Hampl, Richard / Hilakivi-Clarke, Leena / Hubalek, Michael / Iwase, Hirotaka / Jordan, V. Craig / Klocker, Helmut / Kloet, Ronald / Labrie, Fernand / Mendelson, Carole R. / Mück, Alfred O. / Nicola, Alejandro F. / O'Malley, Bert W. / Raynaud, Jean-Pierre / Ruan, Xiangyan / Russo, Jose / Saad, Farid / Sanchez, Edwin R. / Schally, Andrew V. / Schillaci, Roxana / Schindler, Adolf E. / Söderqvist, Gunnar / Speirs, Valerie / Stanczyk, Frank Z. / Starka, Luboslav / Sutter, Thomas R. / Tresguerres, Jesús A. / Wahli, Walter / Wildt, Ludwig / Yang, Kaiping / Yu, Qi

4 Issues per year


CiteScore 2016: 2.15

SCImago Journal Rank (SJR) 2015: 0.432
Source Normalized Impact per Paper (SNIP) 2015: 0.334

Online
ISSN
1868-1891
See all formats and pricing
More options …
Volume 7, Issue 1 (Oct 2011)

Issues

Synthesis of a 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone

Clotilde Ferroud
  • Laboratoire de Transformation Chimique et Pharmaceutique, ERL3193 CNRS/ESPCIParisTech/Cnam, 2 rue Conté, 75003 Paris, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Gilbert Revial
  • Laboratoire de Transformation Chimique et Pharmaceutique, ERL3193 CNRS/ESPCIParisTech/Cnam, 2 rue Conté, 75003 Paris, France
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Christophe Ricco
  • Laboratoire de Transformation Chimique et Pharmaceutique, ERL3193 CNRS/ESPCIParisTech/Cnam, 2 rue Conté, 75003 Paris, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Olivier Hennebert
  • Laboratoire de Biologie EA3199 Conservatoire national des arts et métiers, 2 rue Conté, 75003 Paris, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Robert Morfin
  • Laboratoire de Biologie EA3199 Conservatoire national des arts et métiers, 2 rue Conté, 75003 Paris, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2011-08-30 | DOI: https://doi.org/10.1515/HMBCI.2011.108

Abstract

In order to develop an immunoassay of 7β-hydroxy-epiandrosterone, a stereoselective synthesis of a specific hapten, 7β-hydroxy-19-oxo-androstan 19-(O-carboxymethyl)oxime (17), was performed. This synthesis was achieved in 16% overall yield starting from the well-known 3β-acetoxy-19-hydroxy-5-androsten-17-one (1). After coupling of the alkyl oxime moiety, an allylic oxidation of the C-7 carbon under mild conditions followed by two selective reductions established all the functionalities of the final compound 17.

Keywords: anti-inflammatory compound; stereoselective synthesis; 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone

About the article

Corresponding author: Dr. Gilbert Revial


Received: 2011-03-25

Accepted: 2011-07-19

Published Online: 2011-08-30

Published in Print: 2011-10-01


Citation Information: Hormone Molecular Biology and Clinical Investigation, ISSN (Online) 1868-1891, ISSN (Print) 1868-1883, DOI: https://doi.org/10.1515/HMBCI.2011.108.

Export Citation

©2011 by Walter de Gruyter Berlin Boston. Copyright Clearance Center

Comments (0)

Please log in or register to comment.
Log in