Tricyclics with analgesic and antidepressant activity. 2. [[(Alkylamino)ethyl]thio]dibenzo[b,f]thiepins and 10,11-dihydro derivatives
A series of [[(alkylamino)ethyl]thio]dibenz[b,f]thiepins (III) and their 10,11-dihydro derivatives (IV) was synthesized and subjected to broad analgesic/CNS screening. Preliminary results indicated a combination of analgesic/antidepressant profiles, similar to that observed for the [[(alkylamino)eth...
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| Veröffentlicht in: | Journal of medicinal chemistry 1982-10, Vol.25 (10), p.1150-1153 |
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| container_title | Journal of medicinal chemistry |
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| creator | Ong, Helen H Profitt, James A Anderson, V. B Spaulding, Theodore C Wilker, Jeffrey C Geyer, Harry M |
| description | A series of [[(alkylamino)ethyl]thio]dibenz[b,f]thiepins (III) and their 10,11-dihydro derivatives (IV) was synthesized and subjected to broad analgesic/CNS screening. Preliminary results indicated a combination of analgesic/antidepressant profiles, similar to that observed for the [[(alkylamino)ethyl]thio]dibenz[b,f]oxepins (I) and their corresponding dihydro derivatives (II). The most active congener from the present series, 10b, shows an antinociceptive potency in the pentazocine range as assessed by phenyl-p-quinone-induced writhing (PQW) and tail flick in mice. It is also more than twice as active as imipramine in preventing tetrabenazine-induced ptosis (TBZ), a test widely recognized to be of predictive value for clinically efficacious antidepressants. |
| doi_str_mv | 10.1021/jm00352a010 |
| format | Article |
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The most active congener from the present series, 10b, shows an antinociceptive potency in the pentazocine range as assessed by phenyl-p-quinone-induced writhing (PQW) and tail flick in mice. 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B</creatorcontrib><creatorcontrib>Spaulding, Theodore C</creatorcontrib><creatorcontrib>Wilker, Jeffrey C</creatorcontrib><creatorcontrib>Geyer, Harry M</creatorcontrib><title>Tricyclics with analgesic and antidepressant activity. 2. [[(Alkylamino)ethyl]thio]dibenzo[b,f]thiepins and 10,11-dihydro derivatives</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of [[(alkylamino)ethyl]thio]dibenz[b,f]thiepins (III) and their 10,11-dihydro derivatives (IV) was synthesized and subjected to broad analgesic/CNS screening. Preliminary results indicated a combination of analgesic/antidepressant profiles, similar to that observed for the [[(alkylamino)ethyl]thio]dibenz[b,f]oxepins (I) and their corresponding dihydro derivatives (II). The most active congener from the present series, 10b, shows an antinociceptive potency in the pentazocine range as assessed by phenyl-p-quinone-induced writhing (PQW) and tail flick in mice. It is also more than twice as active as imipramine in preventing tetrabenazine-induced ptosis (TBZ), a test widely recognized to be of predictive value for clinically efficacious antidepressants.</description><subject>5-Hydroxytryptophan - antagonists & inhibitors</subject><subject>Amphetamine - antagonists & inhibitors</subject><subject>Analgesics - chemical synthesis</subject><subject>Animals</subject><subject>Antidepressive Agents, Tricyclic - chemical synthesis</subject><subject>Antipsychotic Agents - chemical synthesis</subject><subject>Apomorphine - antagonists & inhibitors</subject><subject>Benzoquinones</subject><subject>Blepharoptosis - prevention & control</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Dibenzothiepins - chemical synthesis</subject><subject>Dibenzothiepins - pharmacology</subject><subject>Humans</subject><subject>Male</subject><subject>Quinones - antagonists & inhibitors</subject><subject>Rats</subject><subject>Stereotyped Behavior - drug effects</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1982</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1vEzEQxS1EVdLCiTPSnqCo3TC29_NYVYWCKlGVcCGqrIk9S5zuR7CdluXO_41LoooDh9GM5v30RnrD2EsOUw6Cv1t1ADIXCByesAnPBaRZBdlTNgEQIhWFkM_YgfcriBwXcp_tF1xUGS8n7PfMWT3q1mqf3NuwTLDH9jt5q-NkYgVraO3I-zgmqIO9s2GcJmKazOdHp-3t2GJn--EtheXY3oSlHW6MXVD_a5gvTpqHBa1t7_-6cTjhPDV2ORo3JIacvcNoSP4522uw9fRi1w_Z1_fns7OL9PLzh49np5cpiqIOaSUXdZk1Go3gdQmCci3IGBIVUJ6DLHSOFY86iBJFhqYxiJpqzCmXIFEestdb37UbfmzIB9VZr6ltsadh41UFvKzqoo7g8RbUbvDeUaPWznboRsVBPYSu_gk90q92tptFR-aR3aUc9XSrWx_o56OM7lYVpSxzNbv6or59qq-kuLhW15F_s-VRe7UaNi7-xP_38h8BN5qe</recordid><startdate>198210</startdate><enddate>198210</enddate><creator>Ong, Helen H</creator><creator>Profitt, James A</creator><creator>Anderson, V. 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B ; Spaulding, Theodore C ; Wilker, Jeffrey C ; Geyer, Harry M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a269t-83b974fcad219702e5c2edde280e55036c5a81fca027a24adfdaace9a5e5303a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1982</creationdate><topic>5-Hydroxytryptophan - antagonists & inhibitors</topic><topic>Amphetamine - antagonists & inhibitors</topic><topic>Analgesics - chemical synthesis</topic><topic>Animals</topic><topic>Antidepressive Agents, Tricyclic - chemical synthesis</topic><topic>Antipsychotic Agents - chemical synthesis</topic><topic>Apomorphine - antagonists & inhibitors</topic><topic>Benzoquinones</topic><topic>Blepharoptosis - prevention & control</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Dibenzothiepins - chemical synthesis</topic><topic>Dibenzothiepins - pharmacology</topic><topic>Humans</topic><topic>Male</topic><topic>Quinones - antagonists & inhibitors</topic><topic>Rats</topic><topic>Stereotyped Behavior - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ong, Helen H</creatorcontrib><creatorcontrib>Profitt, James A</creatorcontrib><creatorcontrib>Anderson, V. B</creatorcontrib><creatorcontrib>Spaulding, Theodore C</creatorcontrib><creatorcontrib>Wilker, Jeffrey C</creatorcontrib><creatorcontrib>Geyer, Harry M</creatorcontrib><collection>Istex</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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ong, Helen H</au><au>Profitt, James A</au><au>Anderson, V. B</au><au>Spaulding, Theodore C</au><au>Wilker, Jeffrey C</au><au>Geyer, Harry M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tricyclics with analgesic and antidepressant activity. 2. [[(Alkylamino)ethyl]thio]dibenzo[b,f]thiepins and 10,11-dihydro derivatives</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1982-10</date><risdate>1982</risdate><volume>25</volume><issue>10</issue><spage>1150</spage><epage>1153</epage><pages>1150-1153</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of [[(alkylamino)ethyl]thio]dibenz[b,f]thiepins (III) and their 10,11-dihydro derivatives (IV) was synthesized and subjected to broad analgesic/CNS screening. Preliminary results indicated a combination of analgesic/antidepressant profiles, similar to that observed for the [[(alkylamino)ethyl]thio]dibenz[b,f]oxepins (I) and their corresponding dihydro derivatives (II). The most active congener from the present series, 10b, shows an antinociceptive potency in the pentazocine range as assessed by phenyl-p-quinone-induced writhing (PQW) and tail flick in mice. It is also more than twice as active as imipramine in preventing tetrabenazine-induced ptosis (TBZ), a test widely recognized to be of predictive value for clinically efficacious antidepressants.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>6128417</pmid><doi>10.1021/jm00352a010</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1982-10, Vol.25 (10), p.1150-1153 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | 5-Hydroxytryptophan - antagonists & inhibitors Amphetamine - antagonists & inhibitors Analgesics - chemical synthesis Animals Antidepressive Agents, Tricyclic - chemical synthesis Antipsychotic Agents - chemical synthesis Apomorphine - antagonists & inhibitors Benzoquinones Blepharoptosis - prevention & control Chemical Phenomena Chemistry Dibenzothiepins - chemical synthesis Dibenzothiepins - pharmacology Humans Male Quinones - antagonists & inhibitors Rats Stereotyped Behavior - drug effects |
| title | Tricyclics with analgesic and antidepressant activity. 2. [[(Alkylamino)ethyl]thio]dibenzo[b,f]thiepins and 10,11-dihydro derivatives |
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