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Research Article

Pyridyl Substituted Benzocycloalkenes: New Inhibitors of 17α-Hydroxylase/ 17,20-Lyase (P450 17α)

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Pages 113-122 | Received 03 Jan 1994, Published online: 27 Sep 2008

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Ken-ichi KIMURA, Yoshie ITAKURA, Reika GOTO, Masato TOJIMA, Nobumi EGAWA & Makoto YOSHIHAMA. (2007) Inhibition of 17α-Hydroxylase/C17,20-Lyase (CYP17) from Rat Testis by Green Tea Catechins and Black Tea Theaflavins. Bioscience, Biotechnology, and Biochemistry 71:9, pages 2325-2328.
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MARC LE BORGNE, PASCAL MARCHAND, MARIE-RENEE NOURRISSON, DENIS LOQUET, MARTINA PALZER, GUILLAUME LE BAUT & ROLF W. HARTMANN. (2007) Synthesis and biological evaluation of 3-(azolylmethyl)-1H-indoles and 3-(α-azolylbenzyl)-1H-indoles as selective aromatase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 22:5, pages 667-676.
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Marie-Pierre Lézé, Marc Le Borgne, Pascal Marchand, Denis Loquet, Manuela Kogler, Guillaume Le Baut, Anja Palusczak & Rolf W. Hartmann. (2004) 2- and 3-[(Aryl)(azolyl)methyl]indoles as Potential Non-steroidal Aromatase Inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 19:6, pages 549-557.
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Rolf W. Hartmann, Anja Palusczak, Fabrice Lacan, Giacomo Ricci & Renzo Ruzziconi. (2004) CYP 17 and CYP 19 Inhibitors. Evaluation of Fluorine Effects on the Inhibiting Activity of Regioselectively Fluorinated 1-(Naphthalen-2-ylmethyl)imidazoles. Journal of Enzyme Inhibition and Medicinal Chemistry 19:2, pages 145-155.
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Tilman U. Hutschenreuter, Peter B. Ehmer & Rolf W. Hartmann. (2004) Synthesis of Hydroxy Derivatives of Highly Potent Non-steroidal CYP 17 Inhibitors as Potential Metabolites and Evaluation of their Activity by a Non Cellular Assay using Recombinant Human Enzyme. Journal of Enzyme Inhibition and Medicinal Chemistry 19:1, pages 17-32.
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Hassan Y. Aboul-Enein & Suhair Abu-Zaid. (2002) HPLC ENANTIOMERIC RESOLUTION OF NOVEL TETRALONE DERIVATIVES ON CELLULOSE AND AMYLOSE BASED CHIRAL STATIONARY PHASES UNDER NORMAL PHASE MODE. Journal of Liquid Chromatography & Related Technologies 25:7, pages 1077-1084.
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H John Smith, Paul J Nicholls, Claire Simons & Regis Le Lain. (2001) Inhibitors of steroidogenesis as agents for the treatment of hormone-dependent cancers. Expert Opinion on Therapeutic Patents 11:5, pages 789-824.
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Vincent C.O. Njar, Gertrud Grun & Rolf W. Hartmann. (1995) Evaluation of 6,7-Aziridinyl Steroids and Related Compounds as Inhibitors of Aromatase (P-450arom). Journal of Enzyme Inhibition 9:3, pages 195-202.
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Najim A. Al-Masoudi, Nabeel A. Abdul-Rida, Rawaa A. Kadhim, Sebastian J. Krug, Matthias Engel & Bahjat A. Saeed. (2015) Synthesis and CYP17α hydroxylase inhibition activity of new 3α- and 3β-ester derivatives of pregnenolone and related ether analogues. Medicinal Chemistry Research 25:2, pages 310-321.
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Najim A. Al-Masoudi, Kuthiar M. Mahdi, Nabeel A. Abdul-Rida, Bahjat A. Saeed & Mathias Engel. (2015) A new pregnenolone analogues as privileged scaffolds in inhibition of CYP17 hydroxylase enzyme. Synthesis and in silico molecular docking study. Steroids 100, pages 52-59.
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Tomohiro Kaku, Takenori Hitaka, Akio Ojida, Nobuyuki Matsunaga, Mari Adachi, Toshimasa Tanaka, Takahito Hara, Masuo Yamaoka, Masami Kusaka, Teruaki Okuda, Satoru Asahi, Shuichi Furuya & Akihiro Tasaka. (2011) Discovery of orteronel (TAK-700), a naphthylmethylimidazole derivative, as a highly selective 17,20-lyase inhibitor with potential utility in the treatment of prostate cancer. Bioorganic & Medicinal Chemistry 19:21, pages 6383-6399.
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Tomohiro Kaku, Saori Tsujimoto, Nobuyuki Matsunaga, Toshimasa Tanaka, Takahito Hara, Masuo Yamaoka, Masami Kusaka & Akihiro Tasaka. (2011) 17,20-Lyase inhibitors. Part 3: Design, synthesis, and structure–activity relationships of biphenylylmethylimidazole derivatives as novel 17,20-lyase inhibitors. Bioorganic & Medicinal Chemistry 19:7, pages 2428-2442.
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Tomohiro Kaku, Nobuyuki Matsunaga, Akio Ojida, Toshimasa Tanaka, Takahito Hara, Masuo Yamaoka, Masami Kusaka & Akihiro Tasaka. (2011) 17,20-Lyase inhibitors. Part 4: Design, synthesis and structure–activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors. Bioorganic & Medicinal Chemistry 19:5, pages 1751-1770.
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Alison HM Reid, Gerhardt Attard, Elaine Barrie & Johann S de Bono. (2008) CYP17 inhibition as a hormonal strategy for prostate cancer. Nature Clinical Practice Urology 5:11, pages 610-620.
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Frédéric Leroux, Tilman U. Hutschenreuter, Céline Charrière, Rosario Scopelliti & Rolf W. Hartmann. (2003) N ‐(4‐Biphenylmethyl)imidazoles as Potential Therapeutics for the Treatment of Prostate Cancer: Metabolic Robustness Due to Fluorine Substitution? . Helvetica Chimica Acta 86:7, pages 2671-2686.
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Pascal Marchand, Marc Le Borgne, Martina Palzer, Guillaume Le Baut & Rolf W. Hartmann. (2003) Preparation and pharmacological profile of 7-(?-Azolylbenzyl)-1H-indoles and indolines as new aromatase inhibitors. Bioorganic & Medicinal Chemistry Letters 13:9, pages 1553-1555.
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Samer Haidar, Peter B. Ehmer, Stephan Barassin, Christine Batzl-Hartmann & Rolf W. Hartmann. (2003) Effects of novel 17?-hydroxylase/C17, 20-lyase (P450 17, CYP 17) inhibitors on androgen biosynthesis in vitro and in vivo. The Journal of Steroid Biochemistry and Molecular Biology 84:5, pages 555-562.
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Rolf W. Hartmann, Ursula Müller & Peter B. Ehmer. (2003) Discovery of selective CYP11B2 (aldosterone synthase) inhibitors for the therapy of congestive heart failure and myocardial fibrosis. European Journal of Medicinal Chemistry 38:4, pages 363-366.
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Samer Haidar & Rolf W. Hartmann. (2003) C16 and C17 Substituted Derivatives of Pregnenolone and Progesterone as Inhibitors of 17α‐Hydroxylase‐C17, 20‐lyase: Synthesis and Biological Evaluation. Archiv der Pharmazie 335:11-12, pages 526-534.
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Joseph P Burkhart, Philip M Weintraub, Cynthia A Gates, Robert J Resvick, Roy J Vaz, Dirk Friedrich, Michael R Angelastro, Philippe Bey & Norton P Peet. (2002) Novel Steroidal Vinyl Fluorides as Inhibitors of Steroid C17(20) Lyase. Bioorganic & Medicinal Chemistry 10:4, pages 929-934.
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Samer Haidar, Peter B. Ehmer & Rolf W. Hartmann. (2001) Novel steroidal pyrimidyl inhibitors of P450 17 (17α-hydroxylase/C17-20-lyase). Archiv der Pharmazie 334:12, pages 373-374.
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Hassan Y. Aboul-Enein & Imran Ali. (2001) Enantiomeric resolution of some substituted tetralone derivatives on amylose tris(3,5-dimethyl phenylcarbamate) chiral stationary phase in reversed phase mode. Journal of Separation Science 24:10-11, pages 831-834.
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Hassan Y. Aboul-Enein & Imran Ali. (2001) A Comparative Study of the Enantiomeric Resolution of Several Tetralone Derivatives on Macrocyclic Antibiotic Chiral Stationary Phases Using HPLC under Normal Phase Mode. Archiv der Pharmazie 334:7, pages 258-260.
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Samer Haidar, Christian D.P. Klein & Rolf W. Hartmann. (2001) Synthesis and Evaluation of Steroidal Hydroxamic Acids as Inhibitors of P450 17 (17α-Hydroxylase/C17-20-Lyase). Archiv der Pharmazie 334:4, pages 138-140.
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Peter B. Ehmer, Joachim Jose & Rolf W. Hartmann. (2000) Development of a simple and rapid assay for the evaluation of inhibitors of human 17α-hydroxylase-C17,20-lyase (P450cl7) by coexpression of P450cl7 with NADPH-cytochrome-P450-reductase in Escherichia coli. The Journal of Steroid Biochemistry and Molecular Biology 75:1, pages 57-63.
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Yan Zhuang, Bertil G. Wachall & Rolf W. Hartmann. (2000) Novel imidazolyl and triazolyl substituted biphenyl compounds: synthesis and evaluation as nonsteroidal inhibitors of human 17α-hydroxylase-C17, 20-Lyase (P450 17). Bioorganic & Medicinal Chemistry 8:6, pages 1245-1252.
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Bertil G. Wachall, Markus Hector, Yan Zhuang & Rolf W. Hartmann. (1999) Imidazole substituted biphenyls: A new class of highly potent and in vivo active inhibitors of P450 17 as potential therapeutics for treatment of prostate cancer. Bioorganic & Medicinal Chemistry 7:9, pages 1913-1924.
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Dmitry N. Grigoryev, Katsuya Kato, Vincent C.O. Njar, Brian J. Long, Yang-Zhi Ling, Xin Wang, James Mohler & Angela M.H. Brodie. (1999) Cytochrome P450c17-ExpressingEscherichia colias a First-Step Screening System for 17α-Hydroxylase- C17,20-lyase Inhibitors. Analytical Biochemistry 267:2, pages 319-330.
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Pierrick Auvray, Safa Moslemi, Pascal Sourdaine, Sébastien Galopin, Gilles-Eric Séralini, Cécile Enguehard, Patrick Dallemagne, Ronan Bureau, Pascal Sonnet & Sylvain Rault. (1998) Evidence for new non-steroidal human aromatase inhibitors and comparison with equine aromatase inhibition for an understanding of the mammalian active site. European Journal of Medicinal Chemistry 33:6, pages 451-462.
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Geoffrey D. Brown. (1998) The biosynthesis of steroids and triterpenoids. Natural Product Reports 15:6, pages 653.
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Michael Jarman, H. John Smith, Paul J. Nicholls & Claire Simons. (1998) Inhibitors of enzymes of androgen biosynthesis: cytochrome P45017α and 5α-steroid reductase. Natural Product Reports 15:5, pages 495.
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Yan Zhuang, Josef Zapp & Rolf W. Hartmann. (2006) Synthesis of Z ‐ and E ‐1‐Methyl‐2‐(1‐hydroximinoethyl)‐6‐methoxy‐3,4‐dihydronaphthalene and Evaluation as Inhibitors of 17α‐Hydroxylase‐C17,20‐Lyase (P450 17) . Archiv der Pharmazie 330:11, pages 359-361.
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Dorothea Ledergerber, Martin Frotscher & Rolf W. Hartmann. (2006) Novel Highly Active Thromboxane A 2 Synthase Inhibitors Devoid of Carboxylic Groups . Archiv der Pharmazie 330:1-2, pages 1-5.
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Vincent C.O. Njar, Gregory T. Klus & Angela M.H. Brodie. (1996) Nucleophilic vinylic “addition-elimination” substitution reaction of 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene: A novel and general route to 17-substituted steroids. Part 1 - synthesis of novel 17-azolyl-Δ16 steroids; inhibitors of 17α-hydroxylase/17, 20-lyase (17α-lyase). Bioorganic & Medicinal Chemistry Letters 6:22, pages 2777-2782.
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Vincent C.O. Njar, Markus Hector & Rolf W. Hartmann. (1996) 20-Amino and 20,21-aziridinyl pregnene steroids: Development of potent inhibitors of 17?-hydroxylase/C17,20-lyase (P450 17). Bioorganic & Medicinal Chemistry 4:9, pages 1447-1453.
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Thomas F. Sergejew & Rolf W. Hartmann. (1996) Effect of a diphenylethylenediamine platinum complex on steroidogenesis in rats. The Journal of Steroid Biochemistry and Molecular Biology 58:2, pages 243-248.
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Rolf W. Hartmann, Martin Frotscher, Dorothea Ledergerber, Gerald A. Wächter, Gertrud L. Grün & Tom F. Sergejew. (2006) Synthesis and Evaluation of Azole‐Substituted Tetrahydronaphthalenes as Inhibitors of P450 arom, P450 17, and P450 TxA 2 . Archiv der Pharmazie 329:5, pages 251-261.
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Rolf W. Hartmann, Gerald A. Wächter, Tom Sergejew, Rieka Würtz & Jörg Düerkop. (2006) 4,5‐Dihydro‐3‐(2‐pyrazinyl)naphtho[1,2‐ c ]pyrazole: A Potent and Selective Inhibitor of Steroid‐17α‐Hydroxylase‐C17,20‐Lyase (P450 17) . Archiv der Pharmazie 328:7-8, pages 573-575.
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M. Frotscher, G. W?chter & R.W. Hartmann. (1994) FC24 imidazolyl- and 1,2,4-triazolyl-substituted benzocyclohexenes as potent and selective inhibitors of cytochrome P-450 enzymes. European Journal of Pharmaceutical Sciences 2:1-2, pages 106.
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Rolf W. Hartmann. (1994) Selective inhibition of steriodogenic P450 enzymes: current status and future perspectives. European Journal of Pharmaceutical Sciences 2:1-2, pages 15-16.
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