Facile Synthesis of 8-Benzoylthio-2, 6-methano-3-benzazocines and 3-Benzoylthiomorphinans Having Small-Ring Substituents
Synthesis of 3-cyclopropylmethyl-, 3-cyclobutylmethyl-, and 3-methyl-8-benzoylthio-2, 6-methano-3-benzazocines (1j-l) was performed by regio-selective chlorosulfonation of non-narcotic 8-deoxy derivatives (1a-c) followed by reduction and benzoylation. 3-Benzoylthiomorphinans (2h-j) were also obtaine...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1989/08/25, Vol.37(8), pp.2222-2224 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 37 |
| creator | HORI, Mikio IWAMURA, Tatsunori NAGAI), Tokiko MORITA(nee IMAI, Eiji OJI, Hiromasa KATAOKA, Tadashi SHIMIZU, Hiroshi BAN, Masatoshi NOZAKI, Masakatsu NIWA, Masayuki FUJIMURA, Hajime |
| description | Synthesis of 3-cyclopropylmethyl-, 3-cyclobutylmethyl-, and 3-methyl-8-benzoylthio-2, 6-methano-3-benzazocines (1j-l) was performed by regio-selective chlorosulfonation of non-narcotic 8-deoxy derivatives (1a-c) followed by reduction and benzoylation. 3-Benzoylthiomorphinans (2h-j) were also obtained by the same method. Compounds having small-ring substituents (1k, 1l, 2i, 2j) were found to be weak but pure μ- and δ-opioid antagonists. The analgetic activity of 1k was almost equal to that of pentazocine. |
| doi_str_mv | 10.1248/cpb.37.2222 |
| format | Article |
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Compounds having small-ring substituents (1k, 1l, 2i, 2j) were found to be weak but pure μ- and δ-opioid antagonists. The analgetic activity of 1k was almost equal to that of pentazocine.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.37.2222</identifier><identifier>PMID: 2557165</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>2, 6-methano-3-benzazocine ; analgesic ; Analgesics - chemical synthesis ; Animals ; Benzomorphans - chemical synthesis ; Benzomorphans - pharmacology ; Binding, Competitive - drug effects ; Chemistry ; chlorosulfonation ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Male ; Mice ; morphinan ; Morphinans - chemical synthesis ; Morphinans - pharmacology ; nitration ; opioid antagonist ; Organic chemistry ; Pentazocine - analogs & derivatives ; Pentazocine - chemical synthesis ; Pentazocine - pharmacology ; Preparations and properties ; Receptors, Opioid - drug effects ; Receptors, Opioid - metabolism ; regio-selective synthesis ; sulfur compound</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1989/08/25, Vol.37(8), pp.2222-2224</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c607t-ddda7f927d4a348ccf4f5d6657d6b4398793a3a19699f3dc08cfbe90637ab3e63</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,1879,4012,27906,27907,27908</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6748332$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2557165$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>HORI, Mikio</creatorcontrib><creatorcontrib>IWAMURA, Tatsunori</creatorcontrib><creatorcontrib>NAGAI), Tokiko MORITA(nee</creatorcontrib><creatorcontrib>IMAI, Eiji</creatorcontrib><creatorcontrib>OJI, Hiromasa</creatorcontrib><creatorcontrib>KATAOKA, Tadashi</creatorcontrib><creatorcontrib>SHIMIZU, Hiroshi</creatorcontrib><creatorcontrib>BAN, Masatoshi</creatorcontrib><creatorcontrib>NOZAKI, Masakatsu</creatorcontrib><creatorcontrib>NIWA, Masayuki</creatorcontrib><creatorcontrib>FUJIMURA, Hajime</creatorcontrib><title>Facile Synthesis of 8-Benzoylthio-2, 6-methano-3-benzazocines and 3-Benzoylthiomorphinans Having Small-Ring Substituents</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Synthesis of 3-cyclopropylmethyl-, 3-cyclobutylmethyl-, and 3-methyl-8-benzoylthio-2, 6-methano-3-benzazocines (1j-l) was performed by regio-selective chlorosulfonation of non-narcotic 8-deoxy derivatives (1a-c) followed by reduction and benzoylation. 3-Benzoylthiomorphinans (2h-j) were also obtained by the same method. Compounds having small-ring substituents (1k, 1l, 2i, 2j) were found to be weak but pure μ- and δ-opioid antagonists. The analgetic activity of 1k was almost equal to that of pentazocine.</description><subject>2, 6-methano-3-benzazocine</subject><subject>analgesic</subject><subject>Analgesics - chemical synthesis</subject><subject>Animals</subject><subject>Benzomorphans - chemical synthesis</subject><subject>Benzomorphans - pharmacology</subject><subject>Binding, Competitive - drug effects</subject><subject>Chemistry</subject><subject>chlorosulfonation</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Male</subject><subject>Mice</subject><subject>morphinan</subject><subject>Morphinans - chemical synthesis</subject><subject>Morphinans - pharmacology</subject><subject>nitration</subject><subject>opioid antagonist</subject><subject>Organic chemistry</subject><subject>Pentazocine - analogs & derivatives</subject><subject>Pentazocine - chemical synthesis</subject><subject>Pentazocine - pharmacology</subject><subject>Preparations and properties</subject><subject>Receptors, Opioid - drug effects</subject><subject>Receptors, Opioid - metabolism</subject><subject>regio-selective synthesis</subject><subject>sulfur compound</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkEFv1DAQhS1EVZbCiTNSDogLeHEyiR0fS6G0UiUkCudo4jiNK8debAex_fVN2GipD-OR3jfvSY-QNznb5kVZf1K7dgtiW8zvGdnkUApaFQU8JxvGmKQFcHhBXsZ4z1hRMQGn5LSoKpHzakP-XqIyVme3e5cGHU3MfJ_V9LN2D35v02A8LT5mnI46Deg8BdrOEj54ZZyOGboug6f06MNuMA5dzK7wj3F32e2I1tIf_9apjcmkSbsUX5GTHm3Ur9f_jPy6_Prz4orefP92fXF-QxVnItGu61D0shBdiVDWSvVlX3WcV6LjbQmyFhIQMJdcyh46xWrVt1oyDgJb0BzOyPuD7y7435OOqRlNVNpadNpPsZnv6xkXM_jhAKrgYwy6b3bBjBj2Tc6apedm7rkB0Sw9z_Tb1XZqR90d2bXYWX-36hgV2j6gUyYeMS7KGmCx-XLA7mPCO33UMSSjrF4ic1nVS-w6lvT_8oCh0Q4eAXU7ns4</recordid><startdate>1989</startdate><enddate>1989</enddate><creator>HORI, Mikio</creator><creator>IWAMURA, Tatsunori</creator><creator>NAGAI), Tokiko MORITA(nee</creator><creator>IMAI, Eiji</creator><creator>OJI, Hiromasa</creator><creator>KATAOKA, Tadashi</creator><creator>SHIMIZU, Hiroshi</creator><creator>BAN, Masatoshi</creator><creator>NOZAKI, Masakatsu</creator><creator>NIWA, Masayuki</creator><creator>FUJIMURA, Hajime</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</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>1989</creationdate><title>Facile Synthesis of 8-Benzoylthio-2, 6-methano-3-benzazocines and 3-Benzoylthiomorphinans Having Small-Ring Substituents</title><author>HORI, Mikio ; IWAMURA, Tatsunori ; NAGAI), Tokiko MORITA(nee ; IMAI, Eiji ; OJI, Hiromasa ; KATAOKA, Tadashi ; SHIMIZU, Hiroshi ; BAN, Masatoshi ; NOZAKI, Masakatsu ; NIWA, Masayuki ; FUJIMURA, Hajime</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c607t-ddda7f927d4a348ccf4f5d6657d6b4398793a3a19699f3dc08cfbe90637ab3e63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>2, 6-methano-3-benzazocine</topic><topic>analgesic</topic><topic>Analgesics - chemical synthesis</topic><topic>Animals</topic><topic>Benzomorphans - chemical synthesis</topic><topic>Benzomorphans - pharmacology</topic><topic>Binding, Competitive - drug effects</topic><topic>Chemistry</topic><topic>chlorosulfonation</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Male</topic><topic>Mice</topic><topic>morphinan</topic><topic>Morphinans - chemical synthesis</topic><topic>Morphinans - pharmacology</topic><topic>nitration</topic><topic>opioid antagonist</topic><topic>Organic chemistry</topic><topic>Pentazocine - analogs & derivatives</topic><topic>Pentazocine - chemical synthesis</topic><topic>Pentazocine - pharmacology</topic><topic>Preparations and properties</topic><topic>Receptors, Opioid - drug effects</topic><topic>Receptors, Opioid - metabolism</topic><topic>regio-selective synthesis</topic><topic>sulfur compound</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>HORI, Mikio</creatorcontrib><creatorcontrib>IWAMURA, Tatsunori</creatorcontrib><creatorcontrib>NAGAI), Tokiko MORITA(nee</creatorcontrib><creatorcontrib>IMAI, Eiji</creatorcontrib><creatorcontrib>OJI, Hiromasa</creatorcontrib><creatorcontrib>KATAOKA, Tadashi</creatorcontrib><creatorcontrib>SHIMIZU, Hiroshi</creatorcontrib><creatorcontrib>BAN, Masatoshi</creatorcontrib><creatorcontrib>NOZAKI, Masakatsu</creatorcontrib><creatorcontrib>NIWA, Masayuki</creatorcontrib><creatorcontrib>FUJIMURA, Hajime</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>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>HORI, Mikio</au><au>IWAMURA, Tatsunori</au><au>NAGAI), Tokiko MORITA(nee</au><au>IMAI, Eiji</au><au>OJI, Hiromasa</au><au>KATAOKA, Tadashi</au><au>SHIMIZU, Hiroshi</au><au>BAN, Masatoshi</au><au>NOZAKI, Masakatsu</au><au>NIWA, Masayuki</au><au>FUJIMURA, Hajime</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile Synthesis of 8-Benzoylthio-2, 6-methano-3-benzazocines and 3-Benzoylthiomorphinans Having Small-Ring Substituents</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1989</date><risdate>1989</risdate><volume>37</volume><issue>8</issue><spage>2222</spage><epage>2224</epage><pages>2222-2224</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Synthesis of 3-cyclopropylmethyl-, 3-cyclobutylmethyl-, and 3-methyl-8-benzoylthio-2, 6-methano-3-benzazocines (1j-l) was performed by regio-selective chlorosulfonation of non-narcotic 8-deoxy derivatives (1a-c) followed by reduction and benzoylation. 3-Benzoylthiomorphinans (2h-j) were also obtained by the same method. Compounds having small-ring substituents (1k, 1l, 2i, 2j) were found to be weak but pure μ- and δ-opioid antagonists. The analgetic activity of 1k was almost equal to that of pentazocine.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>2557165</pmid><doi>10.1248/cpb.37.2222</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1989/08/25, Vol.37(8), pp.2222-2224 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_79389067 |
| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | 2, 6-methano-3-benzazocine analgesic Analgesics - chemical synthesis Animals Benzomorphans - chemical synthesis Benzomorphans - pharmacology Binding, Competitive - drug effects Chemistry chlorosulfonation Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Male Mice morphinan Morphinans - chemical synthesis Morphinans - pharmacology nitration opioid antagonist Organic chemistry Pentazocine - analogs & derivatives Pentazocine - chemical synthesis Pentazocine - pharmacology Preparations and properties Receptors, Opioid - drug effects Receptors, Opioid - metabolism regio-selective synthesis sulfur compound |
| title | Facile Synthesis of 8-Benzoylthio-2, 6-methano-3-benzazocines and 3-Benzoylthiomorphinans Having Small-Ring Substituents |
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