Synthesis of 2, 3-Dihydro-1, 4-benzodioxin Derivatives. I. : 2-Substituted-5(and 6)-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins
In order to study new sulfonamide diuretics, two series of 6- and 5-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins were synthesized and tested for diuretic and antihypertensive activities in rats. Starting from 4-chloro(or 3, 4-dichloro)-1, 2-dihydroxybenzene, these sulfamoyl compounds were prepared by tw...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1988/09/25, Vol.36(9), pp.3387-3403 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3403 |
|---|---|
| container_issue | 9 |
| container_start_page | 3387 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 36 |
| creator | ITAZAKI, HIROSHI KAWASAKI, AKIKO MATSUURA, MUNENORI UEDA, MOTOHIKO YONETANI, YUKIO NAKAMURA, MASUHISA |
| description | In order to study new sulfonamide diuretics, two series of 6- and 5-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins were synthesized and tested for diuretic and antihypertensive activities in rats. Starting from 4-chloro(or 3, 4-dichloro)-1, 2-dihydroxybenzene, these sulfamoyl compounds were prepared by two different routes. In method A, 6-sulfamoyl compounds (8 or 11) were obtained by conversion of the nitro function into sulfonamide via the Sandmeyer reaction. In method B, 5-sulfamoyl compounds (16) were synthesized by direct introduction of sulfonyl chloride into the dihydrobenzodioxin, followed by amination. The sulfamoyl dihydrobenzodioxins showed lower diuretic and antihypertensive activities than trichloromethiazide. |
| doi_str_mv | 10.1248/cpb.36.3387 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_78722413</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>78722413</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4107-3e3340d643ea33175efc42c99a7b1266966034b0747679b882134ca13cab64893</originalsourceid><addsrcrecordid>eNp1kc-L1DAYhoMo67h68izkIKK4qUm-NEm9yY4_FhY8rJ5Dmn51snTa2aRdHPGPt-OU8eQlObwP7wvPR8hzwQshlX0XdnUBugCw5gFZCVCGlVLCQ7LinFdMgobH5EnOt5zLkhs4I2cgFS-hXJHfN_t-3GCOmQ4tlRcU2Dpu9k0amLigitXY_xqaOPyMPV1jivd-jPeYC3pV0PdUspupzmMcpxEbVr72fUP1G5anrvXbYd-xv4XNfwrzU_Ko9V3GZ8t_Tr5_-vjt8gu7_vr56vLDNQtKcMMAARRvtAL0AMKU2AYlQ1V5UwupdaU1B1Vzo4w2VW2tnB0ELyD4WitbwTl5dezdpeFuwjy6bcwBu873OEzZGWukVAJm8O0RDGnIOWHrdilufdo7wd3BtZtdO9Du4HqmXyy1U73F5sQucuf85ZL7HHzXJt-HmE-YtpbP15ix9RG7zaP_gafcpzGGDg-ToirtYbZannn9X7zxyWEPfwAvuppG</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>78722413</pqid></control><display><type>article</type><title>Synthesis of 2, 3-Dihydro-1, 4-benzodioxin Derivatives. I. : 2-Substituted-5(and 6)-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins</title><source>J-STAGE Free</source><source>MEDLINE</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>ITAZAKI, HIROSHI ; KAWASAKI, AKIKO ; MATSUURA, MUNENORI ; UEDA, MOTOHIKO ; YONETANI, YUKIO ; NAKAMURA, MASUHISA</creator><creatorcontrib>ITAZAKI, HIROSHI ; KAWASAKI, AKIKO ; MATSUURA, MUNENORI ; UEDA, MOTOHIKO ; YONETANI, YUKIO ; NAKAMURA, MASUHISA</creatorcontrib><description>In order to study new sulfonamide diuretics, two series of 6- and 5-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins were synthesized and tested for diuretic and antihypertensive activities in rats. Starting from 4-chloro(or 3, 4-dichloro)-1, 2-dihydroxybenzene, these sulfamoyl compounds were prepared by two different routes. In method A, 6-sulfamoyl compounds (8 or 11) were obtained by conversion of the nitro function into sulfonamide via the Sandmeyer reaction. In method B, 5-sulfamoyl compounds (16) were synthesized by direct introduction of sulfonyl chloride into the dihydrobenzodioxin, followed by amination. The sulfamoyl dihydrobenzodioxins showed lower diuretic and antihypertensive activities than trichloromethiazide.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.36.3387</identifier><identifier>PMID: 3240535</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Antihypertensive Agents - chemical synthesis ; Chemistry ; Dioxins - chemical synthesis ; Dioxins - pharmacology ; Diuretics - chemical synthesis ; Diuretics - pharmacology ; Exact sciences and technology ; Female ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Male ; Mice ; Mice, Inbred Strains ; Organic chemistry ; Preparations and properties ; Rats ; Rats, Inbred Strains ; Sulfonamides ; uricosuric</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1988/09/25, Vol.36(9), pp.3387-3403</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-c4107-3e3340d643ea33175efc42c99a7b1266966034b0747679b882134ca13cab64893</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6880073$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3240535$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>ITAZAKI, HIROSHI</creatorcontrib><creatorcontrib>KAWASAKI, AKIKO</creatorcontrib><creatorcontrib>MATSUURA, MUNENORI</creatorcontrib><creatorcontrib>UEDA, MOTOHIKO</creatorcontrib><creatorcontrib>YONETANI, YUKIO</creatorcontrib><creatorcontrib>NAKAMURA, MASUHISA</creatorcontrib><title>Synthesis of 2, 3-Dihydro-1, 4-benzodioxin Derivatives. I. : 2-Substituted-5(and 6)-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>In order to study new sulfonamide diuretics, two series of 6- and 5-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins were synthesized and tested for diuretic and antihypertensive activities in rats. Starting from 4-chloro(or 3, 4-dichloro)-1, 2-dihydroxybenzene, these sulfamoyl compounds were prepared by two different routes. In method A, 6-sulfamoyl compounds (8 or 11) were obtained by conversion of the nitro function into sulfonamide via the Sandmeyer reaction. In method B, 5-sulfamoyl compounds (16) were synthesized by direct introduction of sulfonyl chloride into the dihydrobenzodioxin, followed by amination. The sulfamoyl dihydrobenzodioxins showed lower diuretic and antihypertensive activities than trichloromethiazide.</description><subject>Animals</subject><subject>Antihypertensive Agents - chemical synthesis</subject><subject>Chemistry</subject><subject>Dioxins - chemical synthesis</subject><subject>Dioxins - pharmacology</subject><subject>Diuretics - chemical synthesis</subject><subject>Diuretics - pharmacology</subject><subject>Exact sciences and technology</subject><subject>Female</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Male</subject><subject>Mice</subject><subject>Mice, Inbred Strains</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><subject>Sulfonamides</subject><subject>uricosuric</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kc-L1DAYhoMo67h68izkIKK4qUm-NEm9yY4_FhY8rJ5Dmn51snTa2aRdHPGPt-OU8eQlObwP7wvPR8hzwQshlX0XdnUBugCw5gFZCVCGlVLCQ7LinFdMgobH5EnOt5zLkhs4I2cgFS-hXJHfN_t-3GCOmQ4tlRcU2Dpu9k0amLigitXY_xqaOPyMPV1jivd-jPeYC3pV0PdUspupzmMcpxEbVr72fUP1G5anrvXbYd-xv4XNfwrzU_Ko9V3GZ8t_Tr5_-vjt8gu7_vr56vLDNQtKcMMAARRvtAL0AMKU2AYlQ1V5UwupdaU1B1Vzo4w2VW2tnB0ELyD4WitbwTl5dezdpeFuwjy6bcwBu873OEzZGWukVAJm8O0RDGnIOWHrdilufdo7wd3BtZtdO9Du4HqmXyy1U73F5sQucuf85ZL7HHzXJt-HmE-YtpbP15ix9RG7zaP_gafcpzGGDg-ToirtYbZannn9X7zxyWEPfwAvuppG</recordid><startdate>1988</startdate><enddate>1988</enddate><creator>ITAZAKI, HIROSHI</creator><creator>KAWASAKI, AKIKO</creator><creator>MATSUURA, MUNENORI</creator><creator>UEDA, MOTOHIKO</creator><creator>YONETANI, YUKIO</creator><creator>NAKAMURA, MASUHISA</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>1988</creationdate><title>Synthesis of 2, 3-Dihydro-1, 4-benzodioxin Derivatives. I. : 2-Substituted-5(and 6)-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins</title><author>ITAZAKI, HIROSHI ; KAWASAKI, AKIKO ; MATSUURA, MUNENORI ; UEDA, MOTOHIKO ; YONETANI, YUKIO ; NAKAMURA, MASUHISA</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4107-3e3340d643ea33175efc42c99a7b1266966034b0747679b882134ca13cab64893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Animals</topic><topic>Antihypertensive Agents - chemical synthesis</topic><topic>Chemistry</topic><topic>Dioxins - chemical synthesis</topic><topic>Dioxins - pharmacology</topic><topic>Diuretics - chemical synthesis</topic><topic>Diuretics - pharmacology</topic><topic>Exact sciences and technology</topic><topic>Female</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Male</topic><topic>Mice</topic><topic>Mice, Inbred Strains</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><topic>Sulfonamides</topic><topic>uricosuric</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ITAZAKI, HIROSHI</creatorcontrib><creatorcontrib>KAWASAKI, AKIKO</creatorcontrib><creatorcontrib>MATSUURA, MUNENORI</creatorcontrib><creatorcontrib>UEDA, MOTOHIKO</creatorcontrib><creatorcontrib>YONETANI, YUKIO</creatorcontrib><creatorcontrib>NAKAMURA, MASUHISA</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>ITAZAKI, HIROSHI</au><au>KAWASAKI, AKIKO</au><au>MATSUURA, MUNENORI</au><au>UEDA, MOTOHIKO</au><au>YONETANI, YUKIO</au><au>NAKAMURA, MASUHISA</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2, 3-Dihydro-1, 4-benzodioxin Derivatives. I. : 2-Substituted-5(and 6)-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1988</date><risdate>1988</risdate><volume>36</volume><issue>9</issue><spage>3387</spage><epage>3403</epage><pages>3387-3403</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>In order to study new sulfonamide diuretics, two series of 6- and 5-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins were synthesized and tested for diuretic and antihypertensive activities in rats. Starting from 4-chloro(or 3, 4-dichloro)-1, 2-dihydroxybenzene, these sulfamoyl compounds were prepared by two different routes. In method A, 6-sulfamoyl compounds (8 or 11) were obtained by conversion of the nitro function into sulfonamide via the Sandmeyer reaction. In method B, 5-sulfamoyl compounds (16) were synthesized by direct introduction of sulfonyl chloride into the dihydrobenzodioxin, followed by amination. The sulfamoyl dihydrobenzodioxins showed lower diuretic and antihypertensive activities than trichloromethiazide.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>3240535</pmid><doi>10.1248/cpb.36.3387</doi><tpages>17</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1988/09/25, Vol.36(9), pp.3387-3403 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_78722413 |
| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Antihypertensive Agents - chemical synthesis Chemistry Dioxins - chemical synthesis Dioxins - pharmacology Diuretics - chemical synthesis Diuretics - pharmacology Exact sciences and technology Female Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Male Mice Mice, Inbred Strains Organic chemistry Preparations and properties Rats Rats, Inbred Strains Sulfonamides uricosuric |
| title | Synthesis of 2, 3-Dihydro-1, 4-benzodioxin Derivatives. I. : 2-Substituted-5(and 6)-sulfamoyl-2, 3-dihydro-1, 4-benzodioxins |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T10%3A52%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%202,%203-Dihydro-1,%204-benzodioxin%20Derivatives.%20I.%20:%202-Substituted-5(and%206)-sulfamoyl-2,%203-dihydro-1,%204-benzodioxins&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=ITAZAKI,%20HIROSHI&rft.date=1988&rft.volume=36&rft.issue=9&rft.spage=3387&rft.epage=3403&rft.pages=3387-3403&rft.issn=0009-2363&rft.eissn=1347-5223&rft.coden=CPBTAL&rft_id=info:doi/10.1248/cpb.36.3387&rft_dat=%3Cproquest_cross%3E78722413%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=78722413&rft_id=info:pmid/3240535&rfr_iscdi=true |