Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5α-pregnan-3-one as an inhibitor of testosterone 5α-reductase

20-(Hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one and the corresponding 3-thione were synthesized with use of 20-(hydroxymethyl)-4-methyl-4-aza-5 alpha-pregnan-3-one as the starting material. The compounds were tested in vitro for inhibition of testosterone 5 alpha-reductase and found to...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of medicinal chemistry 1985-06, Vol.28 (6), p.831-833
Hauptverfasser:	WEINTRAUB, P. M, BLOHM, T. R, LAUGHLIN, M
Format:	Artikel
Sprache:	eng
Schlagworte:	5-alpha Reductase Inhibitors Alicyclic compounds, terpenoids, prostaglandins, steroids Animals Chemistry Enzyme Inhibitors - chemical synthesis Exact sciences and technology In Vitro Techniques Kinetics Male Organic chemistry Oxidoreductases - antagonists & inhibitors Pregnanes - chemical synthesis Pregnanes - pharmacology Preparations and properties Prostate - enzymology Rats Steroids Steroids, Heterocyclic - chemical synthesis Steroids, Heterocyclic - pharmacology
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	833
container_issue	6
container_start_page	831
container_title	Journal of medicinal chemistry
container_volume	28
creator	WEINTRAUB, P. M BLOHM, T. R LAUGHLIN, M
description	20-(Hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one and the corresponding 3-thione were synthesized with use of 20-(hydroxymethyl)-4-methyl-4-aza-5 alpha-pregnan-3-one as the starting material. The compounds were tested in vitro for inhibition of testosterone 5 alpha-reductase and found to be weak inhibitors with Ki's in the 10(-7) range.
doi_str_mv	10.1021/jm00383a026
format	Article
fullrecord	<record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_76177400</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>76177400</sourcerecordid><originalsourceid>FETCH-LOGICAL-p235t-ee0b8a3e79bd7c126381855a1f8438ac27c11f54b7744e00fb9d47925bad13e03</originalsourceid><addsrcrecordid>eNo9kMtKxEAQRRtRxnF05VrIQkQXrdWPvJYy-IIBXeg6VJKKkyFJx-5EJv6VP-I3meDgqi51z70UxdipgGsBUtxsagAVKQQZ7LG58CVwHYHeZ3MAKbkMpDpkR85tYOSEVDM20wBxAOGcfb5YatFiV5rGM4U3Zi_XQ27NdqipWw_VFdf8T40Cv5BLbrbI_Z9v3lp6b7DhipuGPHQeNl7ZrMu07IydyjpynXEd2cmfEpbyPuvQ0TE7KLBydLKbC_Z2f_e6fOSr54en5e2Kt1L5HSeCNEJFYZzmYSZkoCIR-T6KItIqwkyOS1H4Og1DrQmgSONch7H0U8yFIlALdvHX21rz0Y_nJHXpMqoqbMj0LgkDMUZhAs92YJ_WlCetLWu0Q7J71Oif73x0GVaFxSYr3T8Wi0CIWKlfVcR3IQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>76177400</pqid></control><display><type>article</type><title>Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5α-pregnan-3-one as an inhibitor of testosterone 5α-reductase</title><source>ACS Publications</source><source>MEDLINE</source><creator>WEINTRAUB, P. M ; BLOHM, T. R ; LAUGHLIN, M</creator><creatorcontrib>WEINTRAUB, P. M ; BLOHM, T. R ; LAUGHLIN, M</creatorcontrib><description>20-(Hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one and the corresponding 3-thione were synthesized with use of 20-(hydroxymethyl)-4-methyl-4-aza-5 alpha-pregnan-3-one as the starting material. The compounds were tested in vitro for inhibition of testosterone 5 alpha-reductase and found to be weak inhibitors with Ki's in the 10(-7) range.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00383a026</identifier><identifier>PMID: 4009607</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>5-alpha Reductase Inhibitors ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Animals ; Chemistry ; Enzyme Inhibitors - chemical synthesis ; Exact sciences and technology ; In Vitro Techniques ; Kinetics ; Male ; Organic chemistry ; Oxidoreductases - antagonists & inhibitors ; Pregnanes - chemical synthesis ; Pregnanes - pharmacology ; Preparations and properties ; Prostate - enzymology ; Rats ; Steroids ; Steroids, Heterocyclic - chemical synthesis ; Steroids, Heterocyclic - pharmacology</subject><ispartof>Journal of medicinal chemistry, 1985-06, Vol.28 (6), p.831-833</ispartof><rights>1985 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9161193$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/4009607$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>WEINTRAUB, P. M</creatorcontrib><creatorcontrib>BLOHM, T. R</creatorcontrib><creatorcontrib>LAUGHLIN, M</creatorcontrib><title>Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5α-pregnan-3-one as an inhibitor of testosterone 5α-reductase</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>20-(Hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one and the corresponding 3-thione were synthesized with use of 20-(hydroxymethyl)-4-methyl-4-aza-5 alpha-pregnan-3-one as the starting material. The compounds were tested in vitro for inhibition of testosterone 5 alpha-reductase and found to be weak inhibitors with Ki's in the 10(-7) range.</description><subject>5-alpha Reductase Inhibitors</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Animals</subject><subject>Chemistry</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Exact sciences and technology</subject><subject>In Vitro Techniques</subject><subject>Kinetics</subject><subject>Male</subject><subject>Organic chemistry</subject><subject>Oxidoreductases - antagonists & inhibitors</subject><subject>Pregnanes - chemical synthesis</subject><subject>Pregnanes - pharmacology</subject><subject>Preparations and properties</subject><subject>Prostate - enzymology</subject><subject>Rats</subject><subject>Steroids</subject><subject>Steroids, Heterocyclic - chemical synthesis</subject><subject>Steroids, Heterocyclic - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1985</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kMtKxEAQRRtRxnF05VrIQkQXrdWPvJYy-IIBXeg6VJKKkyFJx-5EJv6VP-I3meDgqi51z70UxdipgGsBUtxsagAVKQQZ7LG58CVwHYHeZ3MAKbkMpDpkR85tYOSEVDM20wBxAOGcfb5YatFiV5rGM4U3Zi_XQ27NdqipWw_VFdf8T40Cv5BLbrbI_Z9v3lp6b7DhipuGPHQeNl7ZrMu07IydyjpynXEd2cmfEpbyPuvQ0TE7KLBydLKbC_Z2f_e6fOSr54en5e2Kt1L5HSeCNEJFYZzmYSZkoCIR-T6KItIqwkyOS1H4Og1DrQmgSONch7H0U8yFIlALdvHX21rz0Y_nJHXpMqoqbMj0LgkDMUZhAs92YJ_WlCetLWu0Q7J71Oif73x0GVaFxSYr3T8Wi0CIWKlfVcR3IQ</recordid><startdate>198506</startdate><enddate>198506</enddate><creator>WEINTRAUB, P. M</creator><creator>BLOHM, T. R</creator><creator>LAUGHLIN, M</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>198506</creationdate><title>Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5α-pregnan-3-one as an inhibitor of testosterone 5α-reductase</title><author>WEINTRAUB, P. M ; BLOHM, T. R ; LAUGHLIN, M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p235t-ee0b8a3e79bd7c126381855a1f8438ac27c11f54b7744e00fb9d47925bad13e03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1985</creationdate><topic>5-alpha Reductase Inhibitors</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Animals</topic><topic>Chemistry</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Exact sciences and technology</topic><topic>In Vitro Techniques</topic><topic>Kinetics</topic><topic>Male</topic><topic>Organic chemistry</topic><topic>Oxidoreductases - antagonists & inhibitors</topic><topic>Pregnanes - chemical synthesis</topic><topic>Pregnanes - pharmacology</topic><topic>Preparations and properties</topic><topic>Prostate - enzymology</topic><topic>Rats</topic><topic>Steroids</topic><topic>Steroids, Heterocyclic - chemical synthesis</topic><topic>Steroids, Heterocyclic - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>WEINTRAUB, P. M</creatorcontrib><creatorcontrib>BLOHM, T. R</creatorcontrib><creatorcontrib>LAUGHLIN, M</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>WEINTRAUB, P. M</au><au>BLOHM, T. R</au><au>LAUGHLIN, M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5α-pregnan-3-one as an inhibitor of testosterone 5α-reductase</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1985-06</date><risdate>1985</risdate><volume>28</volume><issue>6</issue><spage>831</spage><epage>833</epage><pages>831-833</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>20-(Hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one and the corresponding 3-thione were synthesized with use of 20-(hydroxymethyl)-4-methyl-4-aza-5 alpha-pregnan-3-one as the starting material. The compounds were tested in vitro for inhibition of testosterone 5 alpha-reductase and found to be weak inhibitors with Ki's in the 10(-7) range.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>4009607</pmid><doi>10.1021/jm00383a026</doi><tpages>3</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0022-2623
ispartof	Journal of medicinal chemistry, 1985-06, Vol.28 (6), p.831-833
issn	0022-2623 1520-4804
language	eng
recordid	cdi_proquest_miscellaneous_76177400
source	ACS Publications; MEDLINE
subjects	5-alpha Reductase Inhibitors Alicyclic compounds, terpenoids, prostaglandins, steroids Animals Chemistry Enzyme Inhibitors - chemical synthesis Exact sciences and technology In Vitro Techniques Kinetics Male Organic chemistry Oxidoreductases - antagonists & inhibitors Pregnanes - chemical synthesis Pregnanes - pharmacology Preparations and properties Prostate - enzymology Rats Steroids Steroids, Heterocyclic - chemical synthesis Steroids, Heterocyclic - pharmacology
title	Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5α-pregnan-3-one as an inhibitor of testosterone 5α-reductase
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T06%3A44%3A21IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Preparation%20of%2020-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5%CE%B1-pregnan-3-one%20as%20an%20inhibitor%20of%20testosterone%205%CE%B1-reductase&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=WEINTRAUB,%20P.%20M&rft.date=1985-06&rft.volume=28&rft.issue=6&rft.spage=831&rft.epage=833&rft.pages=831-833&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm00383a026&rft_dat=%3Cproquest_pubme%3E76177400%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=76177400&rft_id=info:pmid/4009607&rfr_iscdi=true