Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 18
54
Views
17
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of a First Estradiol-Adenosine Hybrid Compound

, , &
Pages 3183-3192 | Received 11 Dec 2002, Published online: 17 Aug 2006

References

  • Horwitz , K.B. and McGuire , W.L. 1978 . Nuclear mechanisms of estrogen action. Effects of estradiol and anti-estrogens on estrogen receptors and nuclear receptor processing . J. Biol. Chem. , 253 : 8185
  • Dickson , R.B. and Lippman , M.E. 1987 . Estrogenic regulation of growth and polypeptide growth factor secretion in human breast carcinoma . Endocrine Rev. , 8 : 29
  • Poulin , R. and Labrie , F. 1986 . Stimulation of cell proliferation and estrogenic response by adrenal C19-delta 5-steroids in the ZR-75-1 human breast cancer cell line . Cancer Res. , 46 : 4933
  • Gurpide , E. , Gusberg , S.B. and Tseng , L. J. 1976 . Estradiol binding and metabolism in human endometrial hyperplasia and adenocarcinoma . Steroid Biochem. , 7 : 891
  • Labrie , F. 1991 . Intracrinology. Molec. Cell. Endocr. , 78C : 113
  • Luu-The , V. , Zhang , Y. , Poirier , D. and Labrie , F. 1995 . J. Characteristics of human types 1, 2 and 3 17beta-hydroxysteroid dehydrogenase activities: oxidation/reduction and inhibition . Steroid Biochem. Molec. Biol. , 55 : 581
  • Labrie , F. , Luu-The , V. , Lin , S.X. , Labrie , C. , Simard , J. , Breton , R. and Bélanger , A. 1997 . The key role of 17beta-hydroxysteroid dehydrogenases in sex steroid biology . Steroids , 62 : 148
  • Penning , T.M. 1996 . 17beta-hydroxysteroid dehydrogenase: inhibitors and inhibitor design . Endocrine-Related Cancer , 3 : 41
  • Tremblay , M.R. , Lin , S.X. and Poirier , D. 2001 . Chemical synthesis of 16beta-propylaminoacyl derivatives of estradiol and their inhibitory potency on type 1 17beta-hydroxysteroid dehydrogenase and binding affinity on steroid receptors . Steroids , 66 : 821
  • Tremblay , M.R. and Poirier , D. J. 1998 . Overview of a rational approach to design type 1 17beta-hydroxysteroid dehydrogenase inhibitors without estrogenic activity: chemical synthesis and biological evaluation . Steroid Biochem. Molec Biol. , 66 : 179
  • Poirier , D. , Dionne , P. and Auger , S. J. 1998 . A 6beta-(thiaheptanamide) derivative of estradiol as inhibitor of 17beta-hydroxysteroid dehydrogenase type 1 . Steroid Biochem. Molec. Biol. , 64 : 83
  • Pelletier , J.D. , Labrie , F. and Poirier , D. 1994 . N-butyl, N-methyl, 11-[3′,17′ beta-(dihydroxy)-1′,3′,5′(10′)-estratrien-16′ alpha-yl]-9(R/S)-bromo undecanamide: synthesis and 17 beta-HSD inhibiting, estrogenic and antiestrogenic activities . Steroids , 59 : 536
  • Ha , S.B. and Nair , V. 1996 . An improved approach to the synthesis of adenosine-5′-N-ethyluronamides of interest as adenosine receptor agonists . Tetrahedron Lett. , 37 : 1567
  • Hampton , A. J. 1961 . Nucleotides. II. A new procedure for the conversion of ribonucleosides to 2′,3′-O-isopropylidene derivatives . Am. Chem. Soc. , 83 : 3640
  • Mitsunobu , O. 1981 . The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products . Synthesis , : 1
  • Shimokawa , S. , Kimura , J. and Mitsunobu , O. 1976 . Studies on nucleosides and nucleotides. V. Selective aroylation of 5′-hydroxyl group of uridine and adenosine . Bull. Chem. Soc. Jpn. , 49 : 3357
  • Gish , D.T. , Kelly , R.C. , Camiener , G.W. and Wechter , W.J. 1971 . Nucleic acids. II. Synthesis of 5′-esters of 1-beta-D-arabinofuranosylcytosine possessing antileukemic and immunosuppressive activity . J. Med. Chem. , 14 : 1159
  • Miyashita , T. , Ashida , N. , Kondoh , K. , Sakata , S. , Machida , H. , Fujii , A. , Ueda , T. and Matsuda , A. 1992 . Synthesis and antitumor activity of acyl and benzyl types of prodrugs of 2′-deoxy-2′-methylidenecytidine . Nucleosides & Nucleotides , 11 : 495

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.