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Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents
A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the α-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and fo...
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| Published in: | Journal of medicinal chemistry 2007-05, Vol.50 (10), p.2450-2458 |
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| Main Authors: | , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a327t-10a97130d670fca8d0a9529068bffe48d6036b047df93d75e6bb369494f2983b3 |
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| cites | cdi_FETCH-LOGICAL-a327t-10a97130d670fca8d0a9529068bffe48d6036b047df93d75e6bb369494f2983b3 |
| container_end_page | 2458 |
| container_issue | 10 |
| container_start_page | 2450 |
| container_title | Journal of medicinal chemistry |
| container_volume | 50 |
| creator | Detsi, Anastasia Bouloumbasi, Dionysia Prousis, Kyriakos C Koufaki, Maria Athanasellis, Giorgos Melagraki, Georgia Afantitis, Antreas Igglessi-Markopoulou, Olga Kontogiorgis, Christos Hadjipavlou-Litina, Dimitra J |
| description | A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the α-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure−activity relationships and an attempt is made to define the structural features required for activity. |
| doi_str_mv | 10.1021/jm061173n |
| format | article |
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The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure−activity relationships and an attempt is made to define the structural features required for activity.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm061173n</identifier><identifier>PMID: 17444626</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amides - chemical synthesis ; Amides - pharmacology ; Animals ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; Antioxidants - chemical synthesis ; Antioxidants - pharmacology ; Biological and medical sciences ; Biphenyl Compounds - chemistry ; Bones, joints and connective tissue. Antiinflammatory agents ; Carrageenan ; Dimethyl Sulfoxide - chemistry ; Edema - chemically induced ; Edema - drug therapy ; Female ; Hydrazines - chemistry ; Hydroxyl Radical - chemistry ; Lipoxygenase Inhibitors - chemical synthesis ; Lipoxygenase Inhibitors - pharmacology ; Male ; Medical sciences ; Oxidation-Reduction ; Pharmacology. Drug treatments ; Picrates ; Quinolones - chemical synthesis ; Quinolones - pharmacology ; Rats ; Rats, Inbred F344 ; Structure-Activity Relationship ; Thioctic Acid - analogs & derivatives ; Thioctic Acid - chemical synthesis ; Thioctic Acid - pharmacology</subject><ispartof>Journal of medicinal chemistry, 2007-05, Vol.50 (10), p.2450-2458</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a327t-10a97130d670fca8d0a9529068bffe48d6036b047df93d75e6bb369494f2983b3</citedby><cites>FETCH-LOGICAL-a327t-10a97130d670fca8d0a9529068bffe48d6036b047df93d75e6bb369494f2983b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18767494$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17444626$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Detsi, Anastasia</creatorcontrib><creatorcontrib>Bouloumbasi, Dionysia</creatorcontrib><creatorcontrib>Prousis, Kyriakos C</creatorcontrib><creatorcontrib>Koufaki, Maria</creatorcontrib><creatorcontrib>Athanasellis, Giorgos</creatorcontrib><creatorcontrib>Melagraki, Georgia</creatorcontrib><creatorcontrib>Afantitis, Antreas</creatorcontrib><creatorcontrib>Igglessi-Markopoulou, Olga</creatorcontrib><creatorcontrib>Kontogiorgis, Christos</creatorcontrib><creatorcontrib>Hadjipavlou-Litina, Dimitra J</creatorcontrib><title>Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the α-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. 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Antiinflammatory agents</subject><subject>Carrageenan</subject><subject>Dimethyl Sulfoxide - chemistry</subject><subject>Edema - chemically induced</subject><subject>Edema - drug therapy</subject><subject>Female</subject><subject>Hydrazines - chemistry</subject><subject>Hydroxyl Radical - chemistry</subject><subject>Lipoxygenase Inhibitors - chemical synthesis</subject><subject>Lipoxygenase Inhibitors - pharmacology</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Oxidation-Reduction</subject><subject>Pharmacology. Drug treatments</subject><subject>Picrates</subject><subject>Quinolones - chemical synthesis</subject><subject>Quinolones - pharmacology</subject><subject>Rats</subject><subject>Rats, Inbred F344</subject><subject>Structure-Activity Relationship</subject><subject>Thioctic Acid - analogs & derivatives</subject><subject>Thioctic Acid - chemical synthesis</subject><subject>Thioctic Acid - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNqF0ctu1DAUAFALgehQWPADyBuQujD4FTtZRi0FxAioOmzYWE5stx4Se7AT1NnzQ_wI34TbGXU2SCz8uPLx9eMC8Jzg1wRT8mY9YkGIZOEBWJCKYsRrzB-CBcaUIiooOwJPcl5jjBmh7DE4IpJzLqhYgF9nNvurAHUw8HIbpusSZhgd_BR_2gFezD7EobRgEUN6LLPSGZvvNqyurU_wz2-09Jvoe9j23sDWmLmfCsiwDZOPN97oMN352xj54AY9jnqKaQvbKxum_BQ8cnrI9tl-PAZfz9-uTt-j5ed3H07bJdKMygkRrBtJGDZCYtfr2pS4og0Wdeec5bURmIkOc2lcw4ysrOg6JhrecEebmnXsGLza5d2k-GO2eVKjz70dBh1snLOSmNeSEfFfSBrJy7G8wJMd7FPMOVmnNsmPOm0Vweq2Nuq-NsW-2Cedu9Gag9wXo4CXe6BzrweXdOh9PrhaClkeUxzaOZ8ne3O_rtN3JSSTlVp9uVTs20WFP_JGnR3y6j6rdZxTKJ_8jwv-Bd3Nshs</recordid><startdate>20070517</startdate><enddate>20070517</enddate><creator>Detsi, Anastasia</creator><creator>Bouloumbasi, Dionysia</creator><creator>Prousis, Kyriakos C</creator><creator>Koufaki, Maria</creator><creator>Athanasellis, Giorgos</creator><creator>Melagraki, Georgia</creator><creator>Afantitis, Antreas</creator><creator>Igglessi-Markopoulou, Olga</creator><creator>Kontogiorgis, Christos</creator><creator>Hadjipavlou-Litina, Dimitra J</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20070517</creationdate><title>Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents</title><author>Detsi, Anastasia ; Bouloumbasi, Dionysia ; Prousis, Kyriakos C ; Koufaki, Maria ; Athanasellis, Giorgos ; Melagraki, Georgia ; Afantitis, Antreas ; Igglessi-Markopoulou, Olga ; Kontogiorgis, Christos ; Hadjipavlou-Litina, Dimitra J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a327t-10a97130d670fca8d0a9529068bffe48d6036b047df93d75e6bb369494f2983b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Amides - chemical synthesis</topic><topic>Amides - pharmacology</topic><topic>Animals</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Carrageenan</topic><topic>Dimethyl Sulfoxide - chemistry</topic><topic>Edema - chemically induced</topic><topic>Edema - drug therapy</topic><topic>Female</topic><topic>Hydrazines - chemistry</topic><topic>Hydroxyl Radical - chemistry</topic><topic>Lipoxygenase Inhibitors - chemical synthesis</topic><topic>Lipoxygenase Inhibitors - pharmacology</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Oxidation-Reduction</topic><topic>Pharmacology. Drug treatments</topic><topic>Picrates</topic><topic>Quinolones - chemical synthesis</topic><topic>Quinolones - pharmacology</topic><topic>Rats</topic><topic>Rats, Inbred F344</topic><topic>Structure-Activity Relationship</topic><topic>Thioctic Acid - analogs & derivatives</topic><topic>Thioctic Acid - chemical synthesis</topic><topic>Thioctic Acid - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Detsi, Anastasia</creatorcontrib><creatorcontrib>Bouloumbasi, Dionysia</creatorcontrib><creatorcontrib>Prousis, Kyriakos C</creatorcontrib><creatorcontrib>Koufaki, Maria</creatorcontrib><creatorcontrib>Athanasellis, Giorgos</creatorcontrib><creatorcontrib>Melagraki, Georgia</creatorcontrib><creatorcontrib>Afantitis, Antreas</creatorcontrib><creatorcontrib>Igglessi-Markopoulou, Olga</creatorcontrib><creatorcontrib>Kontogiorgis, Christos</creatorcontrib><creatorcontrib>Hadjipavlou-Litina, Dimitra J</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>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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Detsi, Anastasia</au><au>Bouloumbasi, Dionysia</au><au>Prousis, Kyriakos C</au><au>Koufaki, Maria</au><au>Athanasellis, Giorgos</au><au>Melagraki, Georgia</au><au>Afantitis, Antreas</au><au>Igglessi-Markopoulou, Olga</au><au>Kontogiorgis, Christos</au><au>Hadjipavlou-Litina, Dimitra J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2007-05-17</date><risdate>2007</risdate><volume>50</volume><issue>10</issue><spage>2450</spage><epage>2458</epage><pages>2450-2458</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the α-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure−activity relationships and an attempt is made to define the structural features required for activity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17444626</pmid><doi>10.1021/jm061173n</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2007-05, Vol.50 (10), p.2450-2458 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70487316 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Amides - chemical synthesis Amides - pharmacology Animals Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - pharmacology Antioxidants - chemical synthesis Antioxidants - pharmacology Biological and medical sciences Biphenyl Compounds - chemistry Bones, joints and connective tissue. Antiinflammatory agents Carrageenan Dimethyl Sulfoxide - chemistry Edema - chemically induced Edema - drug therapy Female Hydrazines - chemistry Hydroxyl Radical - chemistry Lipoxygenase Inhibitors - chemical synthesis Lipoxygenase Inhibitors - pharmacology Male Medical sciences Oxidation-Reduction Pharmacology. Drug treatments Picrates Quinolones - chemical synthesis Quinolones - pharmacology Rats Rats, Inbred F344 Structure-Activity Relationship Thioctic Acid - analogs & derivatives Thioctic Acid - chemical synthesis Thioctic Acid - pharmacology |
| title | Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents |
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