Literature DB >> 23044354

A new simple and high-yield synthesis of 5α-dihydrotestosterone (DHT), a potent androgen receptor agonist.

Puranik Purushottamachar1, Vincent C O Njar.   

Abstract

We have devised an efficient procedure for the synthesis of 5α-dihydrotestosterone (DHT) (1) starting from 3β-hydroxy-5α-androstan-17-one, providing the product in unprecedented 82% yield. A reported method of using toxic Jones reagent is replaced by milder oxidizing agent (NMO/TPAP) in the synthesis of a key intermediate 17β-[(tert-butyldimethylsilyl)oxy]-5α-androstan-3-one (18). This new procedure is simple, does not require special apparatus/precautions or chromatographic purification in most of the steps.
Copyright © 2012 Elsevier Inc. All rights reserved.

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Year:  2012        PMID： 23044354      PMCID： PMC3959746          DOI： 10.1016/j.steroids.2012.09.003

Source DB:  PubMed          Journal:  Steroids        ISSN： 0039-128X            Impact factor:   2.668


  18 in total

1.  (Arene)Cl₂Ru(II) complexes with N-coordinated estrogen and androgen isonicotinates: interaction with sex hormone binding globulin and anticancer activity.

Authors:  Rainer Schobert; Sebastian Seibt; Katharina Effenberger-Neidnicht; Caroline Underhill; Bernhard Biersack; Geoffrey L Hammond
Journal:  Steroids       Date:  2010-12-22       Impact factor: 2.668

2.  Design, synthesis and biological evaluation of nuclear receptor-degradation inducers.

Authors:  Yukihiro Itoh; Risa Kitaguchi; Minoru Ishikawa; Mikihiko Naito; Yuichi Hashimoto
Journal:  Bioorg Med Chem       Date:  2011-09-29       Impact factor: 3.641

3.  Synthesis and biological evaluations of putative metabolically stable analogs of VN/124-1 (TOK-001): head to head anti-tumor efficacy evaluation of VN/124-1 (TOK-001) and abiraterone in LAPC-4 human prostate cancer xenograft model.

Authors:  Robert D Bruno; Tadas S Vasaitis; Lalji K Gediya; Puranik Purushottamachar; Abhijit M Godbole; Zeynep Ates-Alagoz; Angela M H Brodie; Vincent C O Njar
Journal:  Steroids       Date:  2011-06-24       Impact factor: 2.668

Review 4.  Clinical application of 5alpha-reductase inhibitors.

Authors:  A Cilotti; G Danza; M Serio
Journal:  J Endocrinol Invest       Date:  2001-03       Impact factor: 4.256

5.  Hydroxylation of steroids by Fusarium oxysporum, Exophiala jeanselmei and Ceratocystis paradoxa.

Authors:  Patrice C Peart; Kayanne P McCook; Floyd A Russell; William F Reynolds; Paul B Reese
Journal:  Steroids       Date:  2011-07-07       Impact factor: 2.668

6.  Development of two androgen receptor assays using adenoviral transduction of MMTV-luc reporter and/or hAR for endocrine screening.

Authors:  P C Hartig; K L Bobseine; B H Britt; M C Cardon; C R Lambright; V S Wilson; L E Gray
Journal:  Toxicol Sci       Date:  2002-03       Impact factor: 4.849

7.  Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin.

Authors:  T Saartok; E Dahlberg; J A Gustafsson
Journal:  Endocrinology       Date:  1984-06       Impact factor: 4.736

Review 8.  The enzymes, regulation, and genetics of bile acid synthesis.

Authors:  David W Russell
Journal:  Annu Rev Biochem       Date:  2003-01-16       Impact factor: 23.643

9.  Chemical synthesis of 2beta-amino-5alpha-androstane-3alpha,17beta-diol N-derivatives and their antiproliferative effect on HL-60 human leukemia cells.

Authors:  Dominic Thibeault; Jenny Roy; Patrick DeRoy; Donald Poirier
Journal:  Bioorg Med Chem       Date:  2008-03-14       Impact factor: 3.641

10.  Potent anti-prostate cancer agents derived from a novel androgen receptor down-regulating agent.

Authors:  Puranik Purushottamachar; Aakanksha Khandelwal; Tadas S Vasaitis; Robert D Bruno; Lalji K Gediya; Vincent C O Njar
Journal:  Bioorg Med Chem       Date:  2008-02-14       Impact factor: 3.641
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  3 in total

1.  Effect of exogenous testosterone, finasteride, and castration on serum level of thyroxin.

Authors:  Fatemeh Zarei; Namdar Yousofvand; Mozafar Khazaei; Ali Ghanbari
Journal:  Iran Biomed J       Date:  2013

2.  Systematic structure modifications of multitarget prostate cancer drug candidate galeterone to produce novel androgen receptor down-regulating agents as an approach to treatment of advanced prostate cancer.

Authors:  Puranik Purushottamachar; Abhijit M Godbole; Lalji K Gediya; Marlena S Martin; Tadas S Vasaitis; Andrew K Kwegyir-Afful; Senthilmurugan Ramalingam; Zeynep Ates-Alagoz; Vincent C O Njar
Journal:  J Med Chem       Date:  2013-06-07       Impact factor: 7.446

Review 3.  Roles of enhancer RNAs in sex hormone-dependent cancers.

Authors:  Lu Zhang; Xiaoxia Ye; Jieyi Luo; Jiayu Chen; Weirang Zheng; Minhua Wu
Journal:  J Cancer Res Clin Oncol       Date:  2022-01-22       Impact factor: 4.553
  3 in total

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