The nitration of canrenone with acetic anhydride/nitric acid
3-Oxo-17α-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The s...
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| Veröffentlicht in: | Steroids 1997-12, Vol.62 (12), p.762-766 |
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| creator | Megges, Rudolf Weiland, Jürgen Undeutsch, Bernd Büchting, Horst Schön, Rudolf |
| description | 3-Oxo-17α-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The structure of III was determined by chemical and spectral analysis to be the 4-nitro derivative of canrenone. This result is in contrast to the known reactions of II with most other reagents that were found to add at
Δ
6, and also in contrast to the reactions of acetic anhydride/nitric acid with alkenes. Electrophilic substitution at the ambident C4 is discussed as the reaction path. The 4-nitro group enhances the inhibitory activity of II against
Na
+
K
+
-
ATPase
, the target enzyme of the cardioactive digitalis glycosides, which appears to indicate increased cardioactivity. |
| doi_str_mv | 10.1016/S0039-128X(97)00073-1 |
| format | Article |
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Δ
6, and also in contrast to the reactions of acetic anhydride/nitric acid with alkenes. Electrophilic substitution at the ambident C4 is discussed as the reaction path. The 4-nitro group enhances the inhibitory activity of II against
Na
+
K
+
-
ATPase
, the target enzyme of the cardioactive digitalis glycosides, which appears to indicate increased cardioactivity.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/S0039-128X(97)00073-1</identifier><identifier>PMID: 9434341</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>3-oxo-17α-pregna-4,6-diene-21,17-carbolactone ; 4-nitrocanrenone ; Acetic Acid - chemistry ; acetic anhydride/nitric acid nitration ; ambidence ; Biological and medical sciences ; canrenone ; Canrenone - analogs & derivatives ; Canrenone - chemical synthesis ; Canrenone - chemistry ; Canrenone - pharmacology ; electrophilic substitution ; formula omitted ; Fundamental and applied biological sciences. Psychology ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Nitrates - chemistry ; Nitric Acid - chemistry ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet ; Steroid hormones. Cholecalciferol derivatives ; Ultraviolet Rays ; Vertebrates: endocrinology</subject><ispartof>Steroids, 1997-12, Vol.62 (12), p.762-766</ispartof><rights>1997</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-43cd28903c1f0c112b92052b6de1bcdd774bfcceecfc83bf630d8f8b246171da3</citedby><cites>FETCH-LOGICAL-c389t-43cd28903c1f0c112b92052b6de1bcdd774bfcceecfc83bf630d8f8b246171da3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0039128X97000731$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2095455$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9434341$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Megges, Rudolf</creatorcontrib><creatorcontrib>Weiland, Jürgen</creatorcontrib><creatorcontrib>Undeutsch, Bernd</creatorcontrib><creatorcontrib>Büchting, Horst</creatorcontrib><creatorcontrib>Schön, Rudolf</creatorcontrib><title>The nitration of canrenone with acetic anhydride/nitric acid</title><title>Steroids</title><addtitle>Steroids</addtitle><description>3-Oxo-17α-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The structure of III was determined by chemical and spectral analysis to be the 4-nitro derivative of canrenone. This result is in contrast to the known reactions of II with most other reagents that were found to add at
Δ
6, and also in contrast to the reactions of acetic anhydride/nitric acid with alkenes. Electrophilic substitution at the ambident C4 is discussed as the reaction path. The 4-nitro group enhances the inhibitory activity of II against
Na
+
K
+
-
ATPase
, the target enzyme of the cardioactive digitalis glycosides, which appears to indicate increased cardioactivity.</description><subject>3-oxo-17α-pregna-4,6-diene-21,17-carbolactone</subject><subject>4-nitrocanrenone</subject><subject>Acetic Acid - chemistry</subject><subject>acetic anhydride/nitric acid nitration</subject><subject>ambidence</subject><subject>Biological and medical sciences</subject><subject>canrenone</subject><subject>Canrenone - analogs & derivatives</subject><subject>Canrenone - chemical synthesis</subject><subject>Canrenone - chemistry</subject><subject>Canrenone - pharmacology</subject><subject>electrophilic substitution</subject><subject>formula omitted</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Nitrates - chemistry</subject><subject>Nitric Acid - chemistry</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Steroid hormones. Cholecalciferol derivatives</subject><subject>Ultraviolet Rays</subject><subject>Vertebrates: endocrinology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtLAzEQgIMoWh8_QdiDiB7W5rG7SUAQEV8geLCCt5CdTGikzWqyVfz3bm3pVeYwMPPNg4-QY0YvGGXN-IVSoUvG1duZlueUUilKtkVGTElV1qqR22S0QfbIfs7vA9QIzXfJrq7EEGxELidTLGLok-1DF4vOF2BjwthFLL5DPy0sYB-gsHH641JwOF7CywIEd0h2vJ1lPFrnA_J6dzu5eSifnu8fb66fShBK92UlwHGlqQDmKTDGW81pzdvGIWvBOSmr1gMgggclWt8I6pRXLa8aJpmz4oCcrvZ-pO5zgbk385ABZzMbsVtkI3XNK8rpANYrEFKXc0JvPlKY2_RjGDVLa-bPmlkqMVqaP2uGDXPH6wOLdo5uM7XWNPRP1n2bwc58shFC3mCc6rqq6wG7WmE4yPgKmEyGgBHQhYTQG9eFfx75BTLMiWU</recordid><startdate>19971201</startdate><enddate>19971201</enddate><creator>Megges, Rudolf</creator><creator>Weiland, Jürgen</creator><creator>Undeutsch, Bernd</creator><creator>Büchting, Horst</creator><creator>Schön, Rudolf</creator><general>Elsevier Inc</general><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19971201</creationdate><title>The nitration of canrenone with acetic anhydride/nitric acid</title><author>Megges, Rudolf ; Weiland, Jürgen ; Undeutsch, Bernd ; Büchting, Horst ; Schön, Rudolf</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-43cd28903c1f0c112b92052b6de1bcdd774bfcceecfc83bf630d8f8b246171da3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>3-oxo-17α-pregna-4,6-diene-21,17-carbolactone</topic><topic>4-nitrocanrenone</topic><topic>Acetic Acid - chemistry</topic><topic>acetic anhydride/nitric acid nitration</topic><topic>ambidence</topic><topic>Biological and medical sciences</topic><topic>canrenone</topic><topic>Canrenone - analogs & derivatives</topic><topic>Canrenone - chemical synthesis</topic><topic>Canrenone - chemistry</topic><topic>Canrenone - pharmacology</topic><topic>electrophilic substitution</topic><topic>formula omitted</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Nitrates - chemistry</topic><topic>Nitric Acid - chemistry</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Steroid hormones. Cholecalciferol derivatives</topic><topic>Ultraviolet Rays</topic><topic>Vertebrates: endocrinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Megges, Rudolf</creatorcontrib><creatorcontrib>Weiland, Jürgen</creatorcontrib><creatorcontrib>Undeutsch, Bernd</creatorcontrib><creatorcontrib>Büchting, Horst</creatorcontrib><creatorcontrib>Schön, Rudolf</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>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Megges, Rudolf</au><au>Weiland, Jürgen</au><au>Undeutsch, Bernd</au><au>Büchting, Horst</au><au>Schön, Rudolf</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The nitration of canrenone with acetic anhydride/nitric acid</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>1997-12-01</date><risdate>1997</risdate><volume>62</volume><issue>12</issue><spage>762</spage><epage>766</epage><pages>762-766</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>3-Oxo-17α-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The structure of III was determined by chemical and spectral analysis to be the 4-nitro derivative of canrenone. This result is in contrast to the known reactions of II with most other reagents that were found to add at
Δ
6, and also in contrast to the reactions of acetic anhydride/nitric acid with alkenes. Electrophilic substitution at the ambident C4 is discussed as the reaction path. The 4-nitro group enhances the inhibitory activity of II against
Na
+
K
+
-
ATPase
, the target enzyme of the cardioactive digitalis glycosides, which appears to indicate increased cardioactivity.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>9434341</pmid><doi>10.1016/S0039-128X(97)00073-1</doi><tpages>5</tpages></addata></record> |
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| subjects | 3-oxo-17α-pregna-4,6-diene-21,17-carbolactone 4-nitrocanrenone Acetic Acid - chemistry acetic anhydride/nitric acid nitration ambidence Biological and medical sciences canrenone Canrenone - analogs & derivatives Canrenone - chemical synthesis Canrenone - chemistry Canrenone - pharmacology electrophilic substitution formula omitted Fundamental and applied biological sciences. Psychology Magnetic Resonance Spectroscopy Mass Spectrometry Nitrates - chemistry Nitric Acid - chemistry Spectrophotometry, Infrared Spectrophotometry, Ultraviolet Steroid hormones. Cholecalciferol derivatives Ultraviolet Rays Vertebrates: endocrinology |
| title | The nitration of canrenone with acetic anhydride/nitric acid |
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