Synthesis of spiro[chroman-2,4′-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors
A number of spiro[chroman-2,4′-piperdin]-4-one derivatives ( 38a– m and 43a– j) have been designed, synthesized and screened for in vitro ACC inhibition. In vivo studies of compound 38j has been carried out. Various spiro[chroman-2,4′-piperidin]-4-one derivatives ( 38a– m and 43a– j) have been desig...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2009-02, Vol.19 (3), p.949-953 |
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| creator | Shinde, Pundlik Srivastava, Sanjay K. Odedara, Rajendra Tuli, Davinder Munshi, Siralee Patel, Jitendra Zambad, Shitalkumar P. Sonawane, Rajesh Gupta, Ramesh C. Chauthaiwale, Vijay Dutt, Chaitanya |
| description | A number of spiro[chroman-2,4′-piperdin]-4-one derivatives (
38a–
m and
43a–
j) have been designed, synthesized and screened for in vitro ACC inhibition. In vivo studies of compound
38j has been carried out.
Various spiro[chroman-2,4′-piperidin]-4-one derivatives (
38a–
m and
43a–
j) have been designed, synthesized and evaluated for in vitro acetyl-CoA carboxylase (ACC) inhibitory activity. Several compounds have shown ACC inhibitory activity in low nanomolar range. Compound
38j reduced the respiratory quotient (RQ) in C57BL/6J mice indicating increase in whole body fat oxidation even in the presence of high carbohydrate diet. Structure–activity relationship (SAR) has been discussed. |
| doi_str_mv | 10.1016/j.bmcl.2008.11.099 |
| format | Article |
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38a–
m and
43a–
j) have been designed, synthesized and screened for in vitro ACC inhibition. In vivo studies of compound
38j has been carried out.
Various spiro[chroman-2,4′-piperidin]-4-one derivatives (
38a–
m and
43a–
j) have been designed, synthesized and evaluated for in vitro acetyl-CoA carboxylase (ACC) inhibitory activity. Several compounds have shown ACC inhibitory activity in low nanomolar range. Compound
38j reduced the respiratory quotient (RQ) in C57BL/6J mice indicating increase in whole body fat oxidation even in the presence of high carbohydrate diet. Structure–activity relationship (SAR) has been discussed.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2008.11.099</identifier><identifier>PMID: 19097787</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Acetyl-CoA Carboxylase - antagonists & inhibitors ; Acetyl-CoA Carboxylase - chemistry ; Acetyl-CoA carboxylase inhibitors ; Adenosine Triphosphate - chemistry ; Animals ; Biological and medical sciences ; Carbohydrates - chemistry ; Chemistry, Pharmaceutical - methods ; Chromans - chemical synthesis ; Chromans - chemistry ; Chromans - pharmacology ; Drug Design ; General and cellular metabolism. Vitamins ; Inhibitory Concentration 50 ; Medical sciences ; Mice ; Mice, Inbred C57BL ; Models, Chemical ; Pharmacology. Drug treatments ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Spiro Compounds - chemical synthesis ; Spiro Compounds - pharmacology ; Spirochromanones ; Structure-Activity Relationship ; Urea - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2009-02, Vol.19 (3), p.949-953</ispartof><rights>2008 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c416t-6d22d9d72921a20d319bd1af0d4ae580affced8bfd43e44473aa78a1bcd392283</citedby><cites>FETCH-LOGICAL-c416t-6d22d9d72921a20d319bd1af0d4ae580affced8bfd43e44473aa78a1bcd392283</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2008.11.099$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21123458$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19097787$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shinde, Pundlik</creatorcontrib><creatorcontrib>Srivastava, Sanjay K.</creatorcontrib><creatorcontrib>Odedara, Rajendra</creatorcontrib><creatorcontrib>Tuli, Davinder</creatorcontrib><creatorcontrib>Munshi, Siralee</creatorcontrib><creatorcontrib>Patel, Jitendra</creatorcontrib><creatorcontrib>Zambad, Shitalkumar P.</creatorcontrib><creatorcontrib>Sonawane, Rajesh</creatorcontrib><creatorcontrib>Gupta, Ramesh C.</creatorcontrib><creatorcontrib>Chauthaiwale, Vijay</creatorcontrib><creatorcontrib>Dutt, Chaitanya</creatorcontrib><title>Synthesis of spiro[chroman-2,4′-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A number of spiro[chroman-2,4′-piperdin]-4-one derivatives (
38a–
m and
43a–
j) have been designed, synthesized and screened for in vitro ACC inhibition. In vivo studies of compound
38j has been carried out.
Various spiro[chroman-2,4′-piperidin]-4-one derivatives (
38a–
m and
43a–
j) have been designed, synthesized and evaluated for in vitro acetyl-CoA carboxylase (ACC) inhibitory activity. Several compounds have shown ACC inhibitory activity in low nanomolar range. Compound
38j reduced the respiratory quotient (RQ) in C57BL/6J mice indicating increase in whole body fat oxidation even in the presence of high carbohydrate diet. Structure–activity relationship (SAR) has been discussed.</description><subject>Acetyl-CoA Carboxylase - antagonists & inhibitors</subject><subject>Acetyl-CoA Carboxylase - chemistry</subject><subject>Acetyl-CoA carboxylase inhibitors</subject><subject>Adenosine Triphosphate - chemistry</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Carbohydrates - chemistry</subject><subject>Chemistry, Pharmaceutical - methods</subject><subject>Chromans - chemical synthesis</subject><subject>Chromans - chemistry</subject><subject>Chromans - pharmacology</subject><subject>Drug Design</subject><subject>General and cellular metabolism. Vitamins</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred C57BL</subject><subject>Models, Chemical</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - pharmacology</subject><subject>Spirochromanones</subject><subject>Structure-Activity Relationship</subject><subject>Urea - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcGKFDEQhoMo7uzqC3iQvqgX06aSTHcH9rIMrgoLe1BBEAnppJrJ0N1pk57Bue0z7SP5JGaYwb0tFBQF319U_T8hr4CVwKD6sCnbwfYlZ6wpAUqm1BOyAFlJKiRbPiULpipGGyV_nJHzlDaMgWRSPidnoJiq66ZeEPt1P85rTD4VoSvS5GP4adcxDGak_L38e3dPJz9h9M6Pv6ikYcTC5XFnZr_DVJhcFud9T1fhqrAmtuHPvjcJCz-ufevnENML8qwzfcKXp35Bvl9__Lb6TG9uP31ZXd1QK6GaaeU4d8rVXHEwnDkBqnVgOuakwWXDTNdZdE3bOSlQSlkLY-rGQGudUJw34oK8O-6dYvi9xTTrwSeLfW9GDNukayEqAVzJTL59lORMcKUkzyA_gjaGlCJ2eop-MHGvgelDCHqjDyHoQwgaQOcQsuj1afu2HdA9SE6uZ-DNCTDJmr6LZrQ-_ec4ABdyeXjo8shhdm3nMepkPY7ZBR_RztoF_9gd_wD8TKdM</recordid><startdate>20090201</startdate><enddate>20090201</enddate><creator>Shinde, Pundlik</creator><creator>Srivastava, Sanjay K.</creator><creator>Odedara, Rajendra</creator><creator>Tuli, Davinder</creator><creator>Munshi, Siralee</creator><creator>Patel, Jitendra</creator><creator>Zambad, Shitalkumar P.</creator><creator>Sonawane, Rajesh</creator><creator>Gupta, Ramesh C.</creator><creator>Chauthaiwale, Vijay</creator><creator>Dutt, Chaitanya</creator><general>Elsevier Ltd</general><general>Elsevier</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20090201</creationdate><title>Synthesis of spiro[chroman-2,4′-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors</title><author>Shinde, Pundlik ; Srivastava, Sanjay K. ; Odedara, Rajendra ; Tuli, Davinder ; Munshi, Siralee ; Patel, Jitendra ; Zambad, Shitalkumar P. ; Sonawane, Rajesh ; Gupta, Ramesh C. ; Chauthaiwale, Vijay ; Dutt, Chaitanya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c416t-6d22d9d72921a20d319bd1af0d4ae580affced8bfd43e44473aa78a1bcd392283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Acetyl-CoA Carboxylase - antagonists & inhibitors</topic><topic>Acetyl-CoA Carboxylase - chemistry</topic><topic>Acetyl-CoA carboxylase inhibitors</topic><topic>Adenosine Triphosphate - chemistry</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Carbohydrates - chemistry</topic><topic>Chemistry, Pharmaceutical - methods</topic><topic>Chromans - chemical synthesis</topic><topic>Chromans - chemistry</topic><topic>Chromans - pharmacology</topic><topic>Drug Design</topic><topic>General and cellular metabolism. Vitamins</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred C57BL</topic><topic>Models, Chemical</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - pharmacology</topic><topic>Spirochromanones</topic><topic>Structure-Activity Relationship</topic><topic>Urea - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shinde, Pundlik</creatorcontrib><creatorcontrib>Srivastava, Sanjay K.</creatorcontrib><creatorcontrib>Odedara, Rajendra</creatorcontrib><creatorcontrib>Tuli, Davinder</creatorcontrib><creatorcontrib>Munshi, Siralee</creatorcontrib><creatorcontrib>Patel, Jitendra</creatorcontrib><creatorcontrib>Zambad, Shitalkumar P.</creatorcontrib><creatorcontrib>Sonawane, Rajesh</creatorcontrib><creatorcontrib>Gupta, Ramesh C.</creatorcontrib><creatorcontrib>Chauthaiwale, Vijay</creatorcontrib><creatorcontrib>Dutt, Chaitanya</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shinde, Pundlik</au><au>Srivastava, Sanjay K.</au><au>Odedara, Rajendra</au><au>Tuli, Davinder</au><au>Munshi, Siralee</au><au>Patel, Jitendra</au><au>Zambad, Shitalkumar P.</au><au>Sonawane, Rajesh</au><au>Gupta, Ramesh C.</au><au>Chauthaiwale, Vijay</au><au>Dutt, Chaitanya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of spiro[chroman-2,4′-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009-02-01</date><risdate>2009</risdate><volume>19</volume><issue>3</issue><spage>949</spage><epage>953</epage><pages>949-953</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A number of spiro[chroman-2,4′-piperdin]-4-one derivatives (
38a–
m and
43a–
j) have been designed, synthesized and screened for in vitro ACC inhibition. In vivo studies of compound
38j has been carried out.
Various spiro[chroman-2,4′-piperidin]-4-one derivatives (
38a–
m and
43a–
j) have been designed, synthesized and evaluated for in vitro acetyl-CoA carboxylase (ACC) inhibitory activity. Several compounds have shown ACC inhibitory activity in low nanomolar range. Compound
38j reduced the respiratory quotient (RQ) in C57BL/6J mice indicating increase in whole body fat oxidation even in the presence of high carbohydrate diet. Structure–activity relationship (SAR) has been discussed.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19097787</pmid><doi>10.1016/j.bmcl.2008.11.099</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2009-02, Vol.19 (3), p.949-953 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Acetyl-CoA Carboxylase - antagonists & inhibitors Acetyl-CoA Carboxylase - chemistry Acetyl-CoA carboxylase inhibitors Adenosine Triphosphate - chemistry Animals Biological and medical sciences Carbohydrates - chemistry Chemistry, Pharmaceutical - methods Chromans - chemical synthesis Chromans - chemistry Chromans - pharmacology Drug Design General and cellular metabolism. Vitamins Inhibitory Concentration 50 Medical sciences Mice Mice, Inbred C57BL Models, Chemical Pharmacology. Drug treatments Piperidines - chemical synthesis Piperidines - chemistry Spiro Compounds - chemical synthesis Spiro Compounds - pharmacology Spirochromanones Structure-Activity Relationship Urea - chemistry |
| title | Synthesis of spiro[chroman-2,4′-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors |
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