Inhibition of protein glycation by urea and thiourea derivatives of glycine/proline conjugated benzisoxazole analogue – Synthesis and structure–activity studies
Synthesis of a new series of urea/thiourea derivatives of Gly/Pro conjugated benzisoxazole has been reported. Structure of the compounds was characterized by physical and spectroscopical data and has been screened for their in vitro antiglycation activity. Several compounds showed promising activity...
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| Veröffentlicht in: | European journal of medicinal chemistry 2013-02, Vol.60, p.325-332 |
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| container_title | European journal of medicinal chemistry |
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| creator | Shantharam, C.S. Suyoga Vardhan, D.M. Suhas, R. Sridhara, M.B. Gowda, D. Channe |
| description | Synthesis of a new series of urea/thiourea derivatives of Gly/Pro conjugated benzisoxazole has been reported. Structure of the compounds was characterized by physical and spectroscopical data and has been screened for their in vitro antiglycation activity. Several compounds showed promising activity with IC50 |
| doi_str_mv | 10.1016/j.ejmech.2012.12.029 |
| format | Article |
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[Display omitted] This article reports the synthesis, characterization and antiglycation activity of the ureido and thioureido derivatives of Gly/Pro conjugated heterocycle.
▶ Synthesis of novel urea/thiourea derivatives of Gly/Pro conjugated benzisoxazole. ▶ In vitro antiglycation activity. ▶ Several compounds containing –OCH3 and –Br substituents found to be highly active. ▶ Structure–activity relationship has been discussed.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2012.12.029</identifier><identifier>PMID: 23314045</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Amino acids ; Animals ; Antiglycation ; Cattle ; Conjugation ; Dose-Response Relationship, Drug ; Glycine - chemistry ; Isoxazoles - chemistry ; Molecular Structure ; Proline - chemistry ; Serum Albumin, Bovine - antagonists & inhibitors ; Serum Albumin, Bovine - metabolism ; Structure-Activity Relationship ; Urea - analogs & derivatives ; Urea - chemistry ; Urea - pharmacology ; Urea/thiourea</subject><ispartof>European journal of medicinal chemistry, 2013-02, Vol.60, p.325-332</ispartof><rights>2012 Elsevier Masson SAS</rights><rights>Copyright © 2012 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-7a5c015d38ca7383a65810c6583360f166cfc948d996ab118ab8b3984ed1bc0d3</citedby><cites>FETCH-LOGICAL-c362t-7a5c015d38ca7383a65810c6583360f166cfc948d996ab118ab8b3984ed1bc0d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2012.12.029$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23314045$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shantharam, C.S.</creatorcontrib><creatorcontrib>Suyoga Vardhan, D.M.</creatorcontrib><creatorcontrib>Suhas, R.</creatorcontrib><creatorcontrib>Sridhara, M.B.</creatorcontrib><creatorcontrib>Gowda, D. Channe</creatorcontrib><title>Inhibition of protein glycation by urea and thiourea derivatives of glycine/proline conjugated benzisoxazole analogue – Synthesis and structure–activity studies</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Synthesis of a new series of urea/thiourea derivatives of Gly/Pro conjugated benzisoxazole has been reported. Structure of the compounds was characterized by physical and spectroscopical data and has been screened for their in vitro antiglycation activity. Several compounds showed promising activity with IC50 < 5 μM compared to standard rutin (IC50 = 41.9 μM). Further, it was found that compounds containing methoxy and bromine substituents have exerted highly potent activity. Thus, the title compounds represent novel class of potent antiglycating agents.
[Display omitted] This article reports the synthesis, characterization and antiglycation activity of the ureido and thioureido derivatives of Gly/Pro conjugated heterocycle.
▶ Synthesis of novel urea/thiourea derivatives of Gly/Pro conjugated benzisoxazole. ▶ In vitro antiglycation activity. ▶ Several compounds containing –OCH3 and –Br substituents found to be highly active. ▶ Structure–activity relationship has been discussed.</description><subject>Amino acids</subject><subject>Animals</subject><subject>Antiglycation</subject><subject>Cattle</subject><subject>Conjugation</subject><subject>Dose-Response Relationship, Drug</subject><subject>Glycine - chemistry</subject><subject>Isoxazoles - chemistry</subject><subject>Molecular Structure</subject><subject>Proline - chemistry</subject><subject>Serum Albumin, Bovine - antagonists & inhibitors</subject><subject>Serum Albumin, Bovine - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Urea - analogs & derivatives</subject><subject>Urea - chemistry</subject><subject>Urea - pharmacology</subject><subject>Urea/thiourea</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9Uc1uEzEQthCIhrZvgJCPXDb1z67jvVSqqgKVKnEAzpbXnk282tjF9kbdnHgHXoEn40lwksIRaTSjmfm-bzT6EHpLyZISKq6GJQxbMJslI5QtSxDWvkALuhKy4qypX6IFYYxXDeP1GXqT0kAIaQQhr9EZ45zWpG4W6Ne937jOZRc8Dj1-jCGD83g9zkYfh92Mpwgaa29x3rhwbCxEtyv7HaQD64B2Hq4KeywVm-CHaa0zWNyB37sUnvQ-jFBE9BjWE-DfP37iL7PPG0guHbVTjpPJRb2stCnSLs9lOFkH6QK96vWY4PK5nqNvH-6-3n6qHj5_vL-9eagMFyxXK90YQhvLpdErLrkWjaTElMy5ID0VwvSmraVtW6E7SqXuZMdbWYOlnSGWn6P3J93yyPcJUlZblwyMo_YQpqQop0zylvK6QOsT1MSQUoRePUa31XFWlKiDP2pQJ3_UwR9VovhTaO-eL0zdFuw_0l9DCuD6BIDy585BVMk48Aasi2CyssH9_8IfmyOpow</recordid><startdate>201302</startdate><enddate>201302</enddate><creator>Shantharam, C.S.</creator><creator>Suyoga Vardhan, D.M.</creator><creator>Suhas, R.</creator><creator>Sridhara, M.B.</creator><creator>Gowda, D. 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Further, it was found that compounds containing methoxy and bromine substituents have exerted highly potent activity. Thus, the title compounds represent novel class of potent antiglycating agents.
[Display omitted] This article reports the synthesis, characterization and antiglycation activity of the ureido and thioureido derivatives of Gly/Pro conjugated heterocycle.
▶ Synthesis of novel urea/thiourea derivatives of Gly/Pro conjugated benzisoxazole. ▶ In vitro antiglycation activity. ▶ Several compounds containing –OCH3 and –Br substituents found to be highly active. ▶ Structure–activity relationship has been discussed.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>23314045</pmid><doi>10.1016/j.ejmech.2012.12.029</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2013-02, Vol.60, p.325-332 |
| issn | 0223-5234 1768-3254 |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Amino acids Animals Antiglycation Cattle Conjugation Dose-Response Relationship, Drug Glycine - chemistry Isoxazoles - chemistry Molecular Structure Proline - chemistry Serum Albumin, Bovine - antagonists & inhibitors Serum Albumin, Bovine - metabolism Structure-Activity Relationship Urea - analogs & derivatives Urea - chemistry Urea - pharmacology Urea/thiourea |
| title | Inhibition of protein glycation by urea and thiourea derivatives of glycine/proline conjugated benzisoxazole analogue – Synthesis and structure–activity studies |
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