Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity
A series of substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazoles was prepared and evaluated for their saluretic and uricosuric properties. Pharmacological evaluation of the title compounds was carried out in mice, rats, dogs, and monkeys. The diuretic/saluretic nature of these compounds was observe...
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| Veröffentlicht in: | Journal of medicinal chemistry 1984-08, Vol.27 (8), p.1016-1026 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 27 |
| creator | Plattner, Jacob J Fung, Anthony K. L Parks, James A Pariza, Richard J Crowley, Steven R Pernet, Andre G Bunnell, Paul R Dodge, Patrick W |
| description | A series of substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazoles was prepared and evaluated for their saluretic and uricosuric properties. Pharmacological evaluation of the title compounds was carried out in mice, rats, dogs, and monkeys. The diuretic/saluretic nature of these compounds was observed in all species, whereas the uricosuric activity was best seen in the Cebus monkey. Evaluation of the enantiomers of 8-chloro-3-(o-fluorophenyl)-5,6-dihydrofuro [3,2-f]-1,2-benzisoxazole-6-carboxylic acid (15k) revealed that only the (+) enantiomer (29) displayed diuretic and saluretic activity, whereas both enantiomers possessed uricosuric activity. X-ray analysis showed that the (-) enantiomer (30) possesses the 2R configuration. |
| doi_str_mv | 10.1021/jm00374a014 |
| format | Article |
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L ; Parks, James A ; Pariza, Richard J ; Crowley, Steven R ; Pernet, Andre G ; Bunnell, Paul R ; Dodge, Patrick W</creator><creatorcontrib>Plattner, Jacob J ; Fung, Anthony K. L ; Parks, James A ; Pariza, Richard J ; Crowley, Steven R ; Pernet, Andre G ; Bunnell, Paul R ; Dodge, Patrick W</creatorcontrib><description>A series of substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazoles was prepared and evaluated for their saluretic and uricosuric properties. Pharmacological evaluation of the title compounds was carried out in mice, rats, dogs, and monkeys. The diuretic/saluretic nature of these compounds was observed in all species, whereas the uricosuric activity was best seen in the Cebus monkey. Evaluation of the enantiomers of 8-chloro-3-(o-fluorophenyl)-5,6-dihydrofuro [3,2-f]-1,2-benzisoxazole-6-carboxylic acid (15k) revealed that only the (+) enantiomer (29) displayed diuretic and saluretic activity, whereas both enantiomers possessed uricosuric activity. 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Evaluation of the enantiomers of 8-chloro-3-(o-fluorophenyl)-5,6-dihydrofuro [3,2-f]-1,2-benzisoxazole-6-carboxylic acid (15k) revealed that only the (+) enantiomer (29) displayed diuretic and saluretic activity, whereas both enantiomers possessed uricosuric activity. X-ray analysis showed that the (-) enantiomer (30) possesses the 2R configuration.</description><subject>Animals</subject><subject>Chemistry</subject><subject>Chlorides - urine</subject><subject>Diuretics - chemical synthesis</subject><subject>Dogs</subject><subject>Dose-Response Relationship, Drug</subject><subject>Exact sciences and technology</subject><subject>Furans - chemical synthesis</subject><subject>Furans - pharmacology</subject><subject>Haplorhini</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Isoxazoles - chemical synthesis</subject><subject>Isoxazoles - pharmacology</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Natriuresis - drug effects</subject><subject>Organic chemistry</subject><subject>Oxazoles - chemical synthesis</subject><subject>Potassium - urine</subject><subject>Preparations and properties</subject><subject>Rats</subject><subject>Sodium - urine</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Uricosuric Agents - chemical synthesis</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9rFDEUB_AglrpdPXkW5iB6sNH8mmS2NylVCwsVWn-ASMgkL92ss5OaZOxu_3pn2WXx4OW9w_fD4_FF6Dklbylh9N1yRQhXwhAqHqEJrRnBoiHiMZoQwhhmkvEn6CTnJRkdZfwYHUvBKSV8gtbXQ5tLKEMBV9WnEruw2LgU_ZDiD37KsP-J6bha6B9CjmvzEDvAEluT2rjedMFWxgaXz6pFuF1gC6EL_W3lwpCgBJur-1AW1ZCCjXk7R13Cn1A2T9GRN12GZ_s9RV8-XNycf8Lzq4-X5-_n2HBaF-yFsp47MLbmTc0EzAwwwgkoQZR3vq2tFK7h1EhlhXfOMUGVMwCcWPAzPkWvdnfvUvw9QC56FbKFrjM9xCHrhlIl1djHFL3ZQZtizgm8vkthZdJGU6K3Pet_eh71i_3ZoV2BO9h9sWP-cp-bbE3nk-ltyAc2k03TEDkyvGMhF1gfYpN-aam4qvXN52s9Y3Xz7ev8u9761ztvbNbLOKR-7O6_D_4FR1yiCw</recordid><startdate>198408</startdate><enddate>198408</enddate><creator>Plattner, Jacob J</creator><creator>Fung, Anthony K. 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L</creatorcontrib><creatorcontrib>Parks, James A</creatorcontrib><creatorcontrib>Pariza, Richard J</creatorcontrib><creatorcontrib>Crowley, Steven R</creatorcontrib><creatorcontrib>Pernet, Andre G</creatorcontrib><creatorcontrib>Bunnell, Paul R</creatorcontrib><creatorcontrib>Dodge, Patrick W</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><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Plattner, Jacob J</au><au>Fung, Anthony K. L</au><au>Parks, James A</au><au>Pariza, Richard J</au><au>Crowley, Steven R</au><au>Pernet, Andre G</au><au>Bunnell, Paul R</au><au>Dodge, Patrick W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1984-08</date><risdate>1984</risdate><volume>27</volume><issue>8</issue><spage>1016</spage><epage>1026</epage><pages>1016-1026</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazoles was prepared and evaluated for their saluretic and uricosuric properties. Pharmacological evaluation of the title compounds was carried out in mice, rats, dogs, and monkeys. 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| subjects | Animals Chemistry Chlorides - urine Diuretics - chemical synthesis Dogs Dose-Response Relationship, Drug Exact sciences and technology Furans - chemical synthesis Furans - pharmacology Haplorhini Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Isoxazoles - chemical synthesis Isoxazoles - pharmacology Mice Models, Molecular Natriuresis - drug effects Organic chemistry Oxazoles - chemical synthesis Potassium - urine Preparations and properties Rats Sodium - urine Stereoisomerism Structure-Activity Relationship Uricosuric Agents - chemical synthesis |
| title | Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity |
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