Prostaglandin isosteres. 2. Chain-modified thiazolidinone prostaglandin analogs as renal vasodilators
Chain modification of a thiazolidinone prostaglandin isostere has led to the production of 4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl] benzoic acid (5b) which at 1 mg/kg po in the conscious dog causes a 70% increase in renal blood flow over control values with a duration of...
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| Veröffentlicht in: | Journal of medicinal chemistry 1983-03, Vol.26 (3), p.342-348 |
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| container_end_page | 348 |
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| container_issue | 3 |
| container_start_page | 342 |
| container_title | Journal of medicinal chemistry |
| container_volume | 26 |
| creator | Bicking, John B Bock, Mark G Cragoe, Edward J DiPardo, Robert M Gould, Norman Holtz, Wilbur J Lee, T. J Robb, Charles M Smith, Robert L |
| description | Chain modification of a thiazolidinone prostaglandin isostere has led to the production of 4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl] benzoic acid (5b) which at 1 mg/kg po in the conscious dog causes a 70% increase in renal blood flow over control values with a duration of action exceeding 5 h. Preliminary testing indicates that 5b has a relatively specific action on the vasculature of the kidney. The enantiomers of 5b have been separated and the renal vasodilatory activity has been found to be entirely a property of the R-(+) enantiomer. |
| doi_str_mv | 10.1021/jm00357a006 |
| format | Article |
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The enantiomers of 5b have been separated and the renal vasodilatory activity has been found to be entirely a property of the R-(+) enantiomer.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00357a006</identifier><identifier>PMID: 6827556</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Dogs ; Female ; Kidney - blood supply ; Models, Molecular ; Regional Blood Flow - drug effects ; Stereoisomerism ; Thiazoles - pharmacology ; Thiazolidines ; Vascular Resistance - drug effects ; Vasodilation - drug effects ; X-Ray Diffraction</subject><ispartof>Journal of medicinal chemistry, 1983-03, Vol.26 (3), p.342-348</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a354t-39c273a5e28e8c627347a05203f9c64d8d601b39d472f3be7f26577ee52aa98d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00357a006$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00357a006$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6827556$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bicking, John B</creatorcontrib><creatorcontrib>Bock, Mark G</creatorcontrib><creatorcontrib>Cragoe, Edward J</creatorcontrib><creatorcontrib>DiPardo, Robert M</creatorcontrib><creatorcontrib>Gould, Norman</creatorcontrib><creatorcontrib>Holtz, Wilbur J</creatorcontrib><creatorcontrib>Lee, T. 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The enantiomers of 5b have been separated and the renal vasodilatory activity has been found to be entirely a property of the R-(+) enantiomer.</description><subject>Animals</subject><subject>Dogs</subject><subject>Female</subject><subject>Kidney - blood supply</subject><subject>Models, Molecular</subject><subject>Regional Blood Flow - drug effects</subject><subject>Stereoisomerism</subject><subject>Thiazoles - pharmacology</subject><subject>Thiazolidines</subject><subject>Vascular Resistance - drug effects</subject><subject>Vasodilation - drug effects</subject><subject>X-Ray Diffraction</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtLxDAUhYMo4_hYuRa60oV0TJMmaZcyqCMICo6PXbjT3mrGPjTpiPrrvTKDKLjKDee7j3MY20v4KOEiOZ43nEtlgHO9xoaJEjxOM56usyHnQsRCC7nJtkKYc-ISIQdsoDNhlNJDhte-Cz081tCWro1coB96DKNIjKLxE7g2brrSVQ7LqH9y8NnVjsCuxejlTye0UHePIYIQeaQ6eoNAjTX0nQ87bKOCOuDu6t1mt2en0_Ekvrw6vxifXMYgVdrHMi-EkaBQZJgVmuqUXJEfWeWFTsus1DyZybxMjajkDE0ltDIGUQmAPCvlNjtYzqXbXhcYetu4UGBNN2K3CDbj0pg0zQg8WoIFmQgeK_viXQP-wybcfodqf4VK9P5q7GLWYPnDrlIkPV7qjsJ7_5HBP1ttpFF2en1jc3V_N3nIjZ0Qf7jkoQh23i085RX-3fwFSUeOXA</recordid><startdate>198303</startdate><enddate>198303</enddate><creator>Bicking, John B</creator><creator>Bock, Mark G</creator><creator>Cragoe, Edward J</creator><creator>DiPardo, Robert M</creator><creator>Gould, Norman</creator><creator>Holtz, Wilbur J</creator><creator>Lee, T. 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Chain-modified thiazolidinone prostaglandin analogs as renal vasodilators</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1983-03</date><risdate>1983</risdate><volume>26</volume><issue>3</issue><spage>342</spage><epage>348</epage><pages>342-348</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>Chain modification of a thiazolidinone prostaglandin isostere has led to the production of 4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl] benzoic acid (5b) which at 1 mg/kg po in the conscious dog causes a 70% increase in renal blood flow over control values with a duration of action exceeding 5 h. Preliminary testing indicates that 5b has a relatively specific action on the vasculature of the kidney. 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| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1983-03, Vol.26 (3), p.342-348 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_80377448 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Dogs Female Kidney - blood supply Models, Molecular Regional Blood Flow - drug effects Stereoisomerism Thiazoles - pharmacology Thiazolidines Vascular Resistance - drug effects Vasodilation - drug effects X-Ray Diffraction |
| title | Prostaglandin isosteres. 2. Chain-modified thiazolidinone prostaglandin analogs as renal vasodilators |
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