| Synthesis of 17beta-N-substituted 19-Nor-10-azasteroids as inhibitors of human 5alpha-reductases I and II. | |
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MedLine Citation:
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PMID: 12213459 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The synthesis of 17beta-[N-(phenyl)methyl/phenyl-amido] substituted 10-azasteroids has been accomplished by either the TiCl4- or TMSOTf-catalysed reaction of carbamates 11 and 12 with Danishefsky's diene. The reaction provided 5alpha-H isomers 3a-5a and 5beta-H isomers 3b-5b depending on the reaction conditions. Both epimers of each compound were tested against human 5alpha-reductase types I and II. Unexpectedly, 5beta-H compounds were found more active than their 5alpha-H counterparts, the best inhibitors being 3b (IC50=279 and 2000 nM toward isoenzyme I and II, respectively) and 5b (IC50=913 and 247 nM toward isoenzymes I and II, respectively). |
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Authors:
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Dina Scarpi; Ernesto G Occhiato; Giovanna Danza; Mario Serio; Antonio Guarna |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 10 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2002 Nov |
Date Detail:
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Created Date: 2002-09-05 Completed Date: 2003-03-04 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 3455-61 Citation Subset: IM |
Affiliation:
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Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, Via della Lastruccia 13, Sesto Fiorentino, Florence, Italy. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Azasteroids
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chemical synthesis*,
pharmacology* Catalysis Chromatography, Thin Layer Enzyme Inhibitors / chemical synthesis*, pharmacology* Humans Indicators and Reagents Isoenzymes / antagonists & inhibitors Magnetic Resonance Spectroscopy Mass Spectrometry Recombinant Proteins / chemical synthesis, pharmacology Structure-Activity Relationship Testosterone 5-alpha-Reductase / antagonists & inhibitors* |
| Chemical | |
Reg. No./Substance:
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0/Azasteroids; 0/Enzyme Inhibitors; 0/Indicators and Reagents; 0/Isoenzymes; 0/Recombinant Proteins; EC 1.3.99.5/Testosterone 5-alpha-Reductase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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