Loading…
Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)- vibo-quercitol
5-Amino-5-deoxy-1- O-methyl- l- talo-quercitol ( 5), an analogue of strong α-fucosidase inhibitor 5a-carba-fucopyranosylamine ( 3), was synthesized and shown to be a moderate α-fucosidase inhibitor. In continuation of development of bioactive inositol derivatives, a 1- O-methyl derivative of 5-amino...
Saved in:
| Published in: | Bioorganic & medicinal chemistry 2005-07, Vol.13 (13), p.4306-4314 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c381t-2284c21f3ec9a87fad5e57413dd1fea4ea980087fe96f35542ffc19c0890388d3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c381t-2284c21f3ec9a87fad5e57413dd1fea4ea980087fe96f35542ffc19c0890388d3 |
| container_end_page | 4314 |
| container_issue | 13 |
| container_start_page | 4306 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 13 |
| creator | Ogawa, Seiichiro Asada, Miwako Ooki, Yoriko Mori, Midori Itoh, Masayoshi Korenaga, Takashi |
| description | 5-Amino-5-deoxy-1-
O-methyl-
l-
talo-quercitol (
5), an analogue of strong α-fucosidase inhibitor 5a-carba-fucopyranosylamine (
3), was synthesized and shown to be a moderate α-fucosidase inhibitor.
In continuation of development of bioactive inositol derivatives, a 1-
O-methyl derivative of 5-amino-5-deoxy-
l-
talo-quercitol was designed and synthesized as an analogue of the strong α-fucosidase inhibitor, 5a-carba-α-
l-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate α-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxyinositols as hexopyranose mimics of biological interest. |
| doi_str_mv | 10.1016/j.bmc.2005.04.003 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67884642</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089605002853</els_id><sourcerecordid>67884642</sourcerecordid><originalsourceid>FETCH-LOGICAL-c381t-2284c21f3ec9a87fad5e57413dd1fea4ea980087fe96f35542ffc19c0890388d3</originalsourceid><addsrcrecordid>eNp9kM2KFDEQx4Mo7rj6AF4kF0Vh0iadj0nwJOsnLHjRc8gklZ0M3Z016WmcN_DsI_okZpmBvXkKRX71r6ofQs8Z7Rhl6u2-246-6ymVHRUdpfwBWjGhBOHcsIdoRY3ShGqjLtCTWveU0l4Y9hhdMKk3WimzQssHqOlmwm4KuB6nedfKinPEN8PR55qCq4DTtEvbNOeCJXFjmjJh637N14L4ox_yDn65CWaYSx5wgJIWN6cFKo4lj_j1399_3hC8pG0mPw9QfAsanqJH0Q0Vnp3fS_Tj08fvV1_I9bfPX6_eXxPPNZtJ32vhexY5eOP0JrogQW4E4yGwCE6AM5rS9gFGRS6l6GP0zPh2M-VaB36JXp1yb0tuw-tsx1Q9DENbOB-qVRutm7C-gewE-pJrLRDtbUmjK0fLqL2Tbfe2ybZ3si0VtsluPS_O4YftCOG-42y3AS_PgKveDbG4yad6zykteyll496dOGgqlgTFVp9g8hBSAT_bkNN_1vgH-86dvg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67884642</pqid></control><display><type>article</type><title>Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)- vibo-quercitol</title><source>ScienceDirect Freedom Collection</source><creator>Ogawa, Seiichiro ; Asada, Miwako ; Ooki, Yoriko ; Mori, Midori ; Itoh, Masayoshi ; Korenaga, Takashi</creator><creatorcontrib>Ogawa, Seiichiro ; Asada, Miwako ; Ooki, Yoriko ; Mori, Midori ; Itoh, Masayoshi ; Korenaga, Takashi</creatorcontrib><description>5-Amino-5-deoxy-1-
O-methyl-
l-
talo-quercitol (
5), an analogue of strong α-fucosidase inhibitor 5a-carba-fucopyranosylamine (
3), was synthesized and shown to be a moderate α-fucosidase inhibitor.
In continuation of development of bioactive inositol derivatives, a 1-
O-methyl derivative of 5-amino-5-deoxy-
l-
talo-quercitol was designed and synthesized as an analogue of the strong α-fucosidase inhibitor, 5a-carba-α-
l-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate α-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxyinositols as hexopyranose mimics of biological interest.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2005.04.003</identifier><identifier>PMID: 15878669</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>alpha-L-Fucosidase - antagonists & inhibitors ; Analytical, structural and metabolic biochemistry ; Animals ; Biological and medical sciences ; Cattle ; Coffee - enzymology ; Cyclohexanes - chemical synthesis ; Cyclohexanes - chemistry ; Cyclohexanes - pharmacology ; Drug Design ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Enzymes and enzyme inhibitors ; Fundamental and applied biological sciences. Psychology ; Glycoside Hydrolases - antagonists & inhibitors ; Hydrolases ; Kidney - enzymology ; Liver - enzymology ; Molecular Structure ; Prunus - enzymology ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry, 2005-07, Vol.13 (13), p.4306-4314</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-2284c21f3ec9a87fad5e57413dd1fea4ea980087fe96f35542ffc19c0890388d3</citedby><cites>FETCH-LOGICAL-c381t-2284c21f3ec9a87fad5e57413dd1fea4ea980087fe96f35542ffc19c0890388d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16852555$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15878669$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ogawa, Seiichiro</creatorcontrib><creatorcontrib>Asada, Miwako</creatorcontrib><creatorcontrib>Ooki, Yoriko</creatorcontrib><creatorcontrib>Mori, Midori</creatorcontrib><creatorcontrib>Itoh, Masayoshi</creatorcontrib><creatorcontrib>Korenaga, Takashi</creatorcontrib><title>Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)- vibo-quercitol</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>5-Amino-5-deoxy-1-
O-methyl-
l-
talo-quercitol (
5), an analogue of strong α-fucosidase inhibitor 5a-carba-fucopyranosylamine (
3), was synthesized and shown to be a moderate α-fucosidase inhibitor.
In continuation of development of bioactive inositol derivatives, a 1-
O-methyl derivative of 5-amino-5-deoxy-
l-
talo-quercitol was designed and synthesized as an analogue of the strong α-fucosidase inhibitor, 5a-carba-α-
l-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate α-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxyinositols as hexopyranose mimics of biological interest.</description><subject>alpha-L-Fucosidase - antagonists & inhibitors</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cattle</subject><subject>Coffee - enzymology</subject><subject>Cyclohexanes - chemical synthesis</subject><subject>Cyclohexanes - chemistry</subject><subject>Cyclohexanes - pharmacology</subject><subject>Drug Design</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzymes and enzyme inhibitors</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Glycoside Hydrolases - antagonists & inhibitors</subject><subject>Hydrolases</subject><subject>Kidney - enzymology</subject><subject>Liver - enzymology</subject><subject>Molecular Structure</subject><subject>Prunus - enzymology</subject><subject>Structure-Activity Relationship</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNp9kM2KFDEQx4Mo7rj6AF4kF0Vh0iadj0nwJOsnLHjRc8gklZ0M3Z016WmcN_DsI_okZpmBvXkKRX71r6ofQs8Z7Rhl6u2-246-6ymVHRUdpfwBWjGhBOHcsIdoRY3ShGqjLtCTWveU0l4Y9hhdMKk3WimzQssHqOlmwm4KuB6nedfKinPEN8PR55qCq4DTtEvbNOeCJXFjmjJh637N14L4ox_yDn65CWaYSx5wgJIWN6cFKo4lj_j1399_3hC8pG0mPw9QfAsanqJH0Q0Vnp3fS_Tj08fvV1_I9bfPX6_eXxPPNZtJ32vhexY5eOP0JrogQW4E4yGwCE6AM5rS9gFGRS6l6GP0zPh2M-VaB36JXp1yb0tuw-tsx1Q9DENbOB-qVRutm7C-gewE-pJrLRDtbUmjK0fLqL2Tbfe2ybZ3si0VtsluPS_O4YftCOG-42y3AS_PgKveDbG4yad6zykteyll496dOGgqlgTFVp9g8hBSAT_bkNN_1vgH-86dvg</recordid><startdate>20050701</startdate><enddate>20050701</enddate><creator>Ogawa, Seiichiro</creator><creator>Asada, Miwako</creator><creator>Ooki, Yoriko</creator><creator>Mori, Midori</creator><creator>Itoh, Masayoshi</creator><creator>Korenaga, Takashi</creator><general>Elsevier Ltd</general><general>Elsevier Science</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>20050701</creationdate><title>Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)- vibo-quercitol</title><author>Ogawa, Seiichiro ; Asada, Miwako ; Ooki, Yoriko ; Mori, Midori ; Itoh, Masayoshi ; Korenaga, Takashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-2284c21f3ec9a87fad5e57413dd1fea4ea980087fe96f35542ffc19c0890388d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>alpha-L-Fucosidase - antagonists & inhibitors</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cattle</topic><topic>Coffee - enzymology</topic><topic>Cyclohexanes - chemical synthesis</topic><topic>Cyclohexanes - chemistry</topic><topic>Cyclohexanes - pharmacology</topic><topic>Drug Design</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzymes and enzyme inhibitors</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Glycoside Hydrolases - antagonists & inhibitors</topic><topic>Hydrolases</topic><topic>Kidney - enzymology</topic><topic>Liver - enzymology</topic><topic>Molecular Structure</topic><topic>Prunus - enzymology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ogawa, Seiichiro</creatorcontrib><creatorcontrib>Asada, Miwako</creatorcontrib><creatorcontrib>Ooki, Yoriko</creatorcontrib><creatorcontrib>Mori, Midori</creatorcontrib><creatorcontrib>Itoh, Masayoshi</creatorcontrib><creatorcontrib>Korenaga, Takashi</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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ogawa, Seiichiro</au><au>Asada, Miwako</au><au>Ooki, Yoriko</au><au>Mori, Midori</au><au>Itoh, Masayoshi</au><au>Korenaga, Takashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)- vibo-quercitol</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2005-07-01</date><risdate>2005</risdate><volume>13</volume><issue>13</issue><spage>4306</spage><epage>4314</epage><pages>4306-4314</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>5-Amino-5-deoxy-1-
O-methyl-
l-
talo-quercitol (
5), an analogue of strong α-fucosidase inhibitor 5a-carba-fucopyranosylamine (
3), was synthesized and shown to be a moderate α-fucosidase inhibitor.
In continuation of development of bioactive inositol derivatives, a 1-
O-methyl derivative of 5-amino-5-deoxy-
l-
talo-quercitol was designed and synthesized as an analogue of the strong α-fucosidase inhibitor, 5a-carba-α-
l-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate α-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxyinositols as hexopyranose mimics of biological interest.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15878669</pmid><doi>10.1016/j.bmc.2005.04.003</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2005-07, Vol.13 (13), p.4306-4314 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67884642 |
| source | ScienceDirect Freedom Collection |
| subjects | alpha-L-Fucosidase - antagonists & inhibitors Analytical, structural and metabolic biochemistry Animals Biological and medical sciences Cattle Coffee - enzymology Cyclohexanes - chemical synthesis Cyclohexanes - chemistry Cyclohexanes - pharmacology Drug Design Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzymes and enzyme inhibitors Fundamental and applied biological sciences. Psychology Glycoside Hydrolases - antagonists & inhibitors Hydrolases Kidney - enzymology Liver - enzymology Molecular Structure Prunus - enzymology Structure-Activity Relationship |
| title | Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)- vibo-quercitol |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T15%3A20%3A25IST&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=Design%20and%20synthesis%20of%20glycosidase%20inhibitor%205-amino-1,2,3,4-cyclohexanetetrol%20derivatives%20from%20(%E2%88%92)-%20vibo-quercitol&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Ogawa,%20Seiichiro&rft.date=2005-07-01&rft.volume=13&rft.issue=13&rft.spage=4306&rft.epage=4314&rft.pages=4306-4314&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2005.04.003&rft_dat=%3Cproquest_cross%3E67884642%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c381t-2284c21f3ec9a87fad5e57413dd1fea4ea980087fe96f35542ffc19c0890388d3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=67884642&rft_id=info:pmid/15878669&rfr_iscdi=true |