Synthesis and Antiallergenic Properties of 3-n-Pentadecyl- and 3-n-Heptadecylcatechol Esters
A synthetic procedure is described for the preparation of 3-n-pentadecyl- and 3-n-heptadecylcatechols and their acetate and alaninate esters. The Wittig reagent prepared from 2,3-dimethoxybenzyltriphenylphosphonium bromide (III) was coupled with 1-tetradecanal or 1-hexadecanal to give the olefins IV...
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| Veröffentlicht in: | Journal of pharmaceutical sciences 1983-07, Vol.72 (7), p.792-795 |
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| container_title | Journal of pharmaceutical sciences |
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| creator | EiSohlyX, Mahmoud A. Benigni, Daniel A. Torres, Lolita Sue Watson, E. |
| description | A synthetic procedure is described for the preparation of 3-n-pentadecyl- and 3-n-heptadecylcatechols and their acetate and alaninate esters. The Wittig reagent prepared from 2,3-dimethoxybenzyltriphenylphosphonium bromide (III) was coupled with 1-tetradecanal or 1-hexadecanal to give the olefins IV and V, respectively. Catalytic reduction of IV and V followed by demethylation with boron tribromide afforded VIII and IX. The acetates were prepared using acetic anhydride and pyridine, while the alaninates were prepared using N-(tert-butoxycarbonyl)-L-alanine and dicyclohexylcarbodiimide followed by remova of the tert-butoxycarbonyl group with hydrogen chloride gas. The esters were active in guinea pigs in the production of tolerance and desensitization or hyposensitization to poison ivy-type contact dermatitis. |
| doi_str_mv | 10.1002/jps.2600720719 |
| format | Article |
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The Wittig reagent prepared from 2,3-dimethoxybenzyltriphenylphosphonium bromide (III) was coupled with 1-tetradecanal or 1-hexadecanal to give the olefins IV and V, respectively. Catalytic reduction of IV and V followed by demethylation with boron tribromide afforded VIII and IX. The acetates were prepared using acetic anhydride and pyridine, while the alaninates were prepared using N-(tert-butoxycarbonyl)-L-alanine and dicyclohexylcarbodiimide followed by remova of the tert-butoxycarbonyl group with hydrogen chloride gas. The esters were active in guinea pigs in the production of tolerance and desensitization or hyposensitization to poison ivy-type contact dermatitis.</description><identifier>ISSN: 0022-3549</identifier><identifier>EISSN: 1520-6017</identifier><identifier>DOI: 10.1002/jps.2600720719</identifier><identifier>PMID: 6224926</identifier><identifier>CODEN: JPMSAE</identifier><language>eng</language><publisher>Washington: Elsevier Inc</publisher><subject>3-n-Heptadecylcatechol-synthesis ; 3-n-Heptadecylcatechol–synthesis, acetate and alaninate esters ; 3-n-Pentadecylcatechol-synthesis ; 3-n-Pentadecylcatechol–synthesis, acetate and alaninate esters ; acetate and alaninate esters ; Animals ; Catechols - chemical synthesis ; Catechols - pharmacology ; Chemical Phenomena ; Chemistry ; Dermatitis, Toxicodendron - prevention & control ; Exact sciences and technology ; Female ; Guinea Pigs ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; synthesis of saturated congeners ; Synthesis-3-n-pentadecyl- and 3-n-heptadecylcatechols ; Synthesis–3-n-pentadecyl-and 3-n-heptadecylcatechols, acetate and alaninate esters ; Urushiols-poison ivy and poison oak ; Urushiols–poison ivy and poison oak, synthesis of saturated congeners</subject><ispartof>Journal of pharmaceutical sciences, 1983-07, Vol.72 (7), p.792-795</ispartof><rights>1983 Wiley-Liss, Inc., A Wiley Company</rights><rights>Copyright © 1983 Wiley‐Liss, Inc., A Wiley Company</rights><rights>1984 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3719-e563109a5031046f9aa0831a9b3e4d5a5f8bd22a29954f6fd2a15030f86a2f993</citedby><cites>FETCH-LOGICAL-c3719-e563109a5031046f9aa0831a9b3e4d5a5f8bd22a29954f6fd2a15030f86a2f993</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjps.2600720719$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjps.2600720719$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9332013$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6224926$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>EiSohlyX, Mahmoud A.</creatorcontrib><creatorcontrib>Benigni, Daniel A.</creatorcontrib><creatorcontrib>Torres, Lolita</creatorcontrib><creatorcontrib>Sue Watson, E.</creatorcontrib><title>Synthesis and Antiallergenic Properties of 3-n-Pentadecyl- and 3-n-Heptadecylcatechol Esters</title><title>Journal of pharmaceutical sciences</title><addtitle>J. Pharm. Sci</addtitle><description>A synthetic procedure is described for the preparation of 3-n-pentadecyl- and 3-n-heptadecylcatechols and their acetate and alaninate esters. The Wittig reagent prepared from 2,3-dimethoxybenzyltriphenylphosphonium bromide (III) was coupled with 1-tetradecanal or 1-hexadecanal to give the olefins IV and V, respectively. Catalytic reduction of IV and V followed by demethylation with boron tribromide afforded VIII and IX. The acetates were prepared using acetic anhydride and pyridine, while the alaninates were prepared using N-(tert-butoxycarbonyl)-L-alanine and dicyclohexylcarbodiimide followed by remova of the tert-butoxycarbonyl group with hydrogen chloride gas. The esters were active in guinea pigs in the production of tolerance and desensitization or hyposensitization to poison ivy-type contact dermatitis.</description><subject>3-n-Heptadecylcatechol-synthesis</subject><subject>3-n-Heptadecylcatechol–synthesis, acetate and alaninate esters</subject><subject>3-n-Pentadecylcatechol-synthesis</subject><subject>3-n-Pentadecylcatechol–synthesis, acetate and alaninate esters</subject><subject>acetate and alaninate esters</subject><subject>Animals</subject><subject>Catechols - chemical synthesis</subject><subject>Catechols - pharmacology</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Dermatitis, Toxicodendron - prevention & control</subject><subject>Exact sciences and technology</subject><subject>Female</subject><subject>Guinea Pigs</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>synthesis of saturated congeners</subject><subject>Synthesis-3-n-pentadecyl- and 3-n-heptadecylcatechols</subject><subject>Synthesis–3-n-pentadecyl-and 3-n-heptadecylcatechols, acetate and alaninate esters</subject><subject>Urushiols-poison ivy and poison oak</subject><subject>Urushiols–poison ivy and poison oak, synthesis of saturated congeners</subject><issn>0022-3549</issn><issn>1520-6017</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi0EKkvhyg0pB65exnbsrI_VqrTQAiuVjwuSNeuMqUuaRHb42H-PS1aLOCBOI808rz3zMPZUwFIAyBc3Y15KA9BIaIS9xxZCS-AGRHOfLQogudK1fcge5XwDAAa0PmJHRsraSrNgn692_XRNOeYK-7Y66aeIXUfpC_XRV5s0jJSmSLkaQqV4zzfUT9iS33X8d-Cud07jvudxIn89dNVpnijlx-xBwC7Tk309Zh9enr5fn_PLd2ev1ieX3KuyMydtlACLGkqpTbCIsFIC7VZR3WrUYbVtpURpra6DCa1EUVgIK4MyWKuO2XJ-16ch50TBjSneYto5Ae7OkiuW3B9LJfBsDozftrfUHvC9ljJ_vp9j9tiFhL2P-YBZpSQIVTA7Yz9iR7v_fOpeb67-WoHP2VhU_TxkMX11plGNdp_enrmPbzbrC7G-cLrwq5mnIvJ7pOSyj9R7amMiP7l2iP-69hdv1aFh</recordid><startdate>198307</startdate><enddate>198307</enddate><creator>EiSohlyX, Mahmoud A.</creator><creator>Benigni, Daniel A.</creator><creator>Torres, Lolita</creator><creator>Sue Watson, E.</creator><general>Elsevier Inc</general><general>Wiley Subscription Services, Inc., A Wiley Company</general><general>Wiley</general><general>American Pharmaceutical Association</general><scope>BSCLL</scope><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></search><sort><creationdate>198307</creationdate><title>Synthesis and Antiallergenic Properties of 3-n-Pentadecyl- and 3-n-Heptadecylcatechol Esters</title><author>EiSohlyX, Mahmoud A. ; Benigni, Daniel A. ; Torres, Lolita ; Sue Watson, E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3719-e563109a5031046f9aa0831a9b3e4d5a5f8bd22a29954f6fd2a15030f86a2f993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>3-n-Heptadecylcatechol-synthesis</topic><topic>3-n-Heptadecylcatechol–synthesis, acetate and alaninate esters</topic><topic>3-n-Pentadecylcatechol-synthesis</topic><topic>3-n-Pentadecylcatechol–synthesis, acetate and alaninate esters</topic><topic>acetate and alaninate esters</topic><topic>Animals</topic><topic>Catechols - chemical synthesis</topic><topic>Catechols - pharmacology</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Dermatitis, Toxicodendron - prevention & control</topic><topic>Exact sciences and technology</topic><topic>Female</topic><topic>Guinea Pigs</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>synthesis of saturated congeners</topic><topic>Synthesis-3-n-pentadecyl- and 3-n-heptadecylcatechols</topic><topic>Synthesis–3-n-pentadecyl-and 3-n-heptadecylcatechols, acetate and alaninate esters</topic><topic>Urushiols-poison ivy and poison oak</topic><topic>Urushiols–poison ivy and poison oak, synthesis of saturated congeners</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>EiSohlyX, Mahmoud A.</creatorcontrib><creatorcontrib>Benigni, Daniel A.</creatorcontrib><creatorcontrib>Torres, Lolita</creatorcontrib><creatorcontrib>Sue Watson, E.</creatorcontrib><collection>Istex</collection><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><jtitle>Journal of pharmaceutical sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>EiSohlyX, Mahmoud A.</au><au>Benigni, Daniel A.</au><au>Torres, Lolita</au><au>Sue Watson, E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Antiallergenic Properties of 3-n-Pentadecyl- and 3-n-Heptadecylcatechol Esters</atitle><jtitle>Journal of pharmaceutical sciences</jtitle><addtitle>J. Pharm. Sci</addtitle><date>1983-07</date><risdate>1983</risdate><volume>72</volume><issue>7</issue><spage>792</spage><epage>795</epage><pages>792-795</pages><issn>0022-3549</issn><eissn>1520-6017</eissn><coden>JPMSAE</coden><abstract>A synthetic procedure is described for the preparation of 3-n-pentadecyl- and 3-n-heptadecylcatechols and their acetate and alaninate esters. The Wittig reagent prepared from 2,3-dimethoxybenzyltriphenylphosphonium bromide (III) was coupled with 1-tetradecanal or 1-hexadecanal to give the olefins IV and V, respectively. Catalytic reduction of IV and V followed by demethylation with boron tribromide afforded VIII and IX. The acetates were prepared using acetic anhydride and pyridine, while the alaninates were prepared using N-(tert-butoxycarbonyl)-L-alanine and dicyclohexylcarbodiimide followed by remova of the tert-butoxycarbonyl group with hydrogen chloride gas. The esters were active in guinea pigs in the production of tolerance and desensitization or hyposensitization to poison ivy-type contact dermatitis.</abstract><cop>Washington</cop><pub>Elsevier Inc</pub><pmid>6224926</pmid><doi>10.1002/jps.2600720719</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of pharmaceutical sciences, 1983-07, Vol.72 (7), p.792-795 |
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| language | eng |
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| source | MEDLINE; Access via Wiley Online Library; Alma/SFX Local Collection |
| subjects | 3-n-Heptadecylcatechol-synthesis 3-n-Heptadecylcatechol–synthesis, acetate and alaninate esters 3-n-Pentadecylcatechol-synthesis 3-n-Pentadecylcatechol–synthesis, acetate and alaninate esters acetate and alaninate esters Animals Catechols - chemical synthesis Catechols - pharmacology Chemical Phenomena Chemistry Dermatitis, Toxicodendron - prevention & control Exact sciences and technology Female Guinea Pigs Noncondensed benzenic compounds Organic chemistry Preparations and properties synthesis of saturated congeners Synthesis-3-n-pentadecyl- and 3-n-heptadecylcatechols Synthesis–3-n-pentadecyl-and 3-n-heptadecylcatechols, acetate and alaninate esters Urushiols-poison ivy and poison oak Urushiols–poison ivy and poison oak, synthesis of saturated congeners |
| title | Synthesis and Antiallergenic Properties of 3-n-Pentadecyl- and 3-n-Heptadecylcatechol Esters |
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