Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents
Various kinds of N-substituted valiolamine derivatives, including compounds 23a, 24a, and 34a, which are structurally analogous to the key pseudodisaccharides (25a and 26a) of naturally occurring oligosaccharide alpha-D-glucosidase inhibitors, have been synthesized and estimated by the measure of in...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 1986-06, Vol.29 (6), p.1038-1046 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1046 |
|---|---|
| container_issue | 6 |
| container_start_page | 1038 |
| container_title | Journal of medicinal chemistry |
| container_volume | 29 |
| creator | Horii, Satoshi Fukase, Hiroshi Matsuo, Takao Kameda, Yukihiko Asano, Naoki Matsui, Katsuhiko |
| description | Various kinds of N-substituted valiolamine derivatives, including compounds 23a, 24a, and 34a, which are structurally analogous to the key pseudodisaccharides (25a and 26a) of naturally occurring oligosaccharide alpha-D-glucosidase inhibitors, have been synthesized and estimated by the measure of inhibitory activity against porcine sucrase and maltase. The N-substituted valiolamine derivatives evaluated in this study have been found to be more potent than the corresponding N-substituted valienamine derivatives as well as the parent valiolamine. It is noteworthy that even simple N-substituted valiolamine derivatives such as N-[2-hydroxy-1-(hydroxymethyl)ethyl]-, N-[(1R,2R)-2-hydroxycyclohexyl]-, and N-[(R)-(-)-beta-hydroxyphenethyl]valiolamine (6, 8a, and 9a) have the stronger alpha-D-glucosidase inhibitory activity against porcine intestinal maltase and sucrase than naturally occurring oligosaccharide alpha-D-glucosidase inhibitors. |
| doi_str_mv | 10.1021/jm00156a023 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_76864640</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>76864640</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-99a5984da835fbd6bb203bac3cb84f0c83990d68b6b704777e370b09c64d72593</originalsourceid><addsrcrecordid>eNpt0E-L1DAYBvAiyjqunjwLOYgepGOatElzlFVXYVkXZsVjePOnOxnbZsybDs4X8HPbYYbBg5ck8Px4CE9RvKzosqKser8ZKK0aAZTxR8Wiahgt65bWj4sFpYyVTDD-tHiGuKGU8orxi-KCN5VSQi2KP6v9mNceAxIYHVlCv13DsvxYPvSTjRgcoCdhXAcTckx7AjaHXch7EjtyW-JkMIc8Ze_IDvoQexjC6InzKexgln6uRbKN2Y85QE9img-Y3y6A8TlYAg9zhM-LJx306F-c7svi--dP91dfyptv11-vPtyUwNsql0pBo9raQcubzjhhDKPcgOXWtHVHbcuVok60RhhJayml55IaqqyonWSN4pfFm2PvNsVfk8esh4DW9z2MPk6opWhFLWo6w3dHaFNETL7T2xQGSHtdUX1YXf-z-qxfnWonM3h3tqeZ5_z1KQe00HcJRhvwzFrZSFkfWHlkAbP_fY4h_dRCctno-7uVvvtxK5sVu9YH__bowaLexCmN83b__eBfJdunlg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>76864640</pqid></control><display><type>article</type><title>Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents</title><source>MEDLINE</source><source>ACS Publications</source><creator>Horii, Satoshi ; Fukase, Hiroshi ; Matsuo, Takao ; Kameda, Yukihiko ; Asano, Naoki ; Matsui, Katsuhiko</creator><creatorcontrib>Horii, Satoshi ; Fukase, Hiroshi ; Matsuo, Takao ; Kameda, Yukihiko ; Asano, Naoki ; Matsui, Katsuhiko</creatorcontrib><description>Various kinds of N-substituted valiolamine derivatives, including compounds 23a, 24a, and 34a, which are structurally analogous to the key pseudodisaccharides (25a and 26a) of naturally occurring oligosaccharide alpha-D-glucosidase inhibitors, have been synthesized and estimated by the measure of inhibitory activity against porcine sucrase and maltase. The N-substituted valiolamine derivatives evaluated in this study have been found to be more potent than the corresponding N-substituted valienamine derivatives as well as the parent valiolamine. It is noteworthy that even simple N-substituted valiolamine derivatives such as N-[2-hydroxy-1-(hydroxymethyl)ethyl]-, N-[(1R,2R)-2-hydroxycyclohexyl]-, and N-[(R)-(-)-beta-hydroxyphenethyl]valiolamine (6, 8a, and 9a) have the stronger alpha-D-glucosidase inhibitory activity against porcine intestinal maltase and sucrase than naturally occurring oligosaccharide alpha-D-glucosidase inhibitors.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00156a023</identifier><identifier>PMID: 3519969</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Cyclohexanols - chemical synthesis ; Cyclohexanols - pharmacology ; Exact sciences and technology ; Glucosidases - antagonists & inhibitors ; Glycoside Hydrolase Inhibitors ; Hypoglycemic Agents - chemical synthesis ; Hypoglycemic Agents - pharmacology ; Inositol - analogs & derivatives ; Inositol - chemical synthesis ; Inositol - pharmacology ; Organic chemistry ; Preparations and properties ; Stereoisomerism ; Structure-Activity Relationship ; Swine</subject><ispartof>Journal of medicinal chemistry, 1986-06, Vol.29 (6), p.1038-1046</ispartof><rights>1986 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-99a5984da835fbd6bb203bac3cb84f0c83990d68b6b704777e370b09c64d72593</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/jm00156a023$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00156a023$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8757749$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3519969$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Horii, Satoshi</creatorcontrib><creatorcontrib>Fukase, Hiroshi</creatorcontrib><creatorcontrib>Matsuo, Takao</creatorcontrib><creatorcontrib>Kameda, Yukihiko</creatorcontrib><creatorcontrib>Asano, Naoki</creatorcontrib><creatorcontrib>Matsui, Katsuhiko</creatorcontrib><title>Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Various kinds of N-substituted valiolamine derivatives, including compounds 23a, 24a, and 34a, which are structurally analogous to the key pseudodisaccharides (25a and 26a) of naturally occurring oligosaccharide alpha-D-glucosidase inhibitors, have been synthesized and estimated by the measure of inhibitory activity against porcine sucrase and maltase. The N-substituted valiolamine derivatives evaluated in this study have been found to be more potent than the corresponding N-substituted valienamine derivatives as well as the parent valiolamine. It is noteworthy that even simple N-substituted valiolamine derivatives such as N-[2-hydroxy-1-(hydroxymethyl)ethyl]-, N-[(1R,2R)-2-hydroxycyclohexyl]-, and N-[(R)-(-)-beta-hydroxyphenethyl]valiolamine (6, 8a, and 9a) have the stronger alpha-D-glucosidase inhibitory activity against porcine intestinal maltase and sucrase than naturally occurring oligosaccharide alpha-D-glucosidase inhibitors.</description><subject>Animals</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Cyclohexanols - chemical synthesis</subject><subject>Cyclohexanols - pharmacology</subject><subject>Exact sciences and technology</subject><subject>Glucosidases - antagonists & inhibitors</subject><subject>Glycoside Hydrolase Inhibitors</subject><subject>Hypoglycemic Agents - chemical synthesis</subject><subject>Hypoglycemic Agents - pharmacology</subject><subject>Inositol - analogs & derivatives</subject><subject>Inositol - chemical synthesis</subject><subject>Inositol - pharmacology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Swine</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E-L1DAYBvAiyjqunjwLOYgepGOatElzlFVXYVkXZsVjePOnOxnbZsybDs4X8HPbYYbBg5ck8Px4CE9RvKzosqKser8ZKK0aAZTxR8Wiahgt65bWj4sFpYyVTDD-tHiGuKGU8orxi-KCN5VSQi2KP6v9mNceAxIYHVlCv13DsvxYPvSTjRgcoCdhXAcTckx7AjaHXch7EjtyW-JkMIc8Ze_IDvoQexjC6InzKexgln6uRbKN2Y85QE9img-Y3y6A8TlYAg9zhM-LJx306F-c7svi--dP91dfyptv11-vPtyUwNsql0pBo9raQcubzjhhDKPcgOXWtHVHbcuVok60RhhJayml55IaqqyonWSN4pfFm2PvNsVfk8esh4DW9z2MPk6opWhFLWo6w3dHaFNETL7T2xQGSHtdUX1YXf-z-qxfnWonM3h3tqeZ5_z1KQe00HcJRhvwzFrZSFkfWHlkAbP_fY4h_dRCctno-7uVvvtxK5sVu9YH__bowaLexCmN83b__eBfJdunlg</recordid><startdate>19860601</startdate><enddate>19860601</enddate><creator>Horii, Satoshi</creator><creator>Fukase, Hiroshi</creator><creator>Matsuo, Takao</creator><creator>Kameda, Yukihiko</creator><creator>Asano, Naoki</creator><creator>Matsui, Katsuhiko</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>19860601</creationdate><title>Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents</title><author>Horii, Satoshi ; Fukase, Hiroshi ; Matsuo, Takao ; Kameda, Yukihiko ; Asano, Naoki ; Matsui, Katsuhiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-99a5984da835fbd6bb203bac3cb84f0c83990d68b6b704777e370b09c64d72593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Animals</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Cyclohexanols - chemical synthesis</topic><topic>Cyclohexanols - pharmacology</topic><topic>Exact sciences and technology</topic><topic>Glucosidases - antagonists & inhibitors</topic><topic>Glycoside Hydrolase Inhibitors</topic><topic>Hypoglycemic Agents - chemical synthesis</topic><topic>Hypoglycemic Agents - pharmacology</topic><topic>Inositol - analogs & derivatives</topic><topic>Inositol - chemical synthesis</topic><topic>Inositol - pharmacology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Swine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Horii, Satoshi</creatorcontrib><creatorcontrib>Fukase, Hiroshi</creatorcontrib><creatorcontrib>Matsuo, Takao</creatorcontrib><creatorcontrib>Kameda, Yukihiko</creatorcontrib><creatorcontrib>Asano, Naoki</creatorcontrib><creatorcontrib>Matsui, Katsuhiko</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>Horii, Satoshi</au><au>Fukase, Hiroshi</au><au>Matsuo, Takao</au><au>Kameda, Yukihiko</au><au>Asano, Naoki</au><au>Matsui, Katsuhiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1986-06-01</date><risdate>1986</risdate><volume>29</volume><issue>6</issue><spage>1038</spage><epage>1046</epage><pages>1038-1046</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Various kinds of N-substituted valiolamine derivatives, including compounds 23a, 24a, and 34a, which are structurally analogous to the key pseudodisaccharides (25a and 26a) of naturally occurring oligosaccharide alpha-D-glucosidase inhibitors, have been synthesized and estimated by the measure of inhibitory activity against porcine sucrase and maltase. The N-substituted valiolamine derivatives evaluated in this study have been found to be more potent than the corresponding N-substituted valienamine derivatives as well as the parent valiolamine. It is noteworthy that even simple N-substituted valiolamine derivatives such as N-[2-hydroxy-1-(hydroxymethyl)ethyl]-, N-[(1R,2R)-2-hydroxycyclohexyl]-, and N-[(R)-(-)-beta-hydroxyphenethyl]valiolamine (6, 8a, and 9a) have the stronger alpha-D-glucosidase inhibitory activity against porcine intestinal maltase and sucrase than naturally occurring oligosaccharide alpha-D-glucosidase inhibitors.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>3519969</pmid><doi>10.1021/jm00156a023</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1986-06, Vol.29 (6), p.1038-1046 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_76864640 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Cyclohexanols - chemical synthesis Cyclohexanols - pharmacology Exact sciences and technology Glucosidases - antagonists & inhibitors Glycoside Hydrolase Inhibitors Hypoglycemic Agents - chemical synthesis Hypoglycemic Agents - pharmacology Inositol - analogs & derivatives Inositol - chemical synthesis Inositol - pharmacology Organic chemistry Preparations and properties Stereoisomerism Structure-Activity Relationship Swine |
| title | Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T13%3A40%3A50IST&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%20and%20.alpha.-D-glucosidase%20inhibitory%20activity%20of%20N-substituted%20valiolamine%20derivatives%20as%20potential%20oral%20antidiabetic%20agents&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Horii,%20Satoshi&rft.date=1986-06-01&rft.volume=29&rft.issue=6&rft.spage=1038&rft.epage=1046&rft.pages=1038-1046&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm00156a023&rft_dat=%3Cproquest_cross%3E76864640%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=76864640&rft_id=info:pmid/3519969&rfr_iscdi=true |