Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and QSAR study of their DPPH• radical scavenging activity
The in vitro antioxidant activities of eight 3-carboxycoumarin derivatives were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazil (DPPH•) radical scavenging activity method. 3-Acetyl-6-hydroxy-2H-1-benzopyran-2-one (C1) and ethyl 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate (C2) presented t...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2012-12, Vol.17 (12), p.14882-14898 |
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| creator | Martínez-Martínez, Francisco J Razo-Hernández, Rodrigo Said Peraza-Campos, Ana Lilia Villanueva-García, Manuel Sumaya-Martínez, Maria Teresa Cano, Daniel Jaramillo Gómez-Sandoval, Zeferino |
| description | The in vitro antioxidant activities of eight 3-carboxycoumarin derivatives were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazil (DPPH•) radical scavenging activity method. 3-Acetyl-6-hydroxy-2H-1-benzopyran-2-one (C1) and ethyl 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate (C2) presented the best radical-scavenging activity. A quantitative structure-activity relationship (QSAR) study was performed and correlated with the experimental DPPH• scavenging data. We used structural, geometrical, topological and quantum-chemical descriptors selected with Genetic Algorithms in order to determine which of these parameters are responsible of the observed DPPH• radical scavenging activity. We constructed a back propagation neural network with the hydrophilic factor (Hy) descriptor to generate an adequate architecture of neurons for the system description. The mathematical model showed a multiple determination coefficient of 0.9196 and a root mean squared error of 0.0851. Our results shows that the presence of hydroxyl groups on the ring structure of 3-carboxy-coumarins are correlated with the observed DPPH• radical scavenging activity effects. |
| doi_str_mv | 10.3390/molecules171214882 |
| format | Article |
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A quantitative structure-activity relationship (QSAR) study was performed and correlated with the experimental DPPH• scavenging data. We used structural, geometrical, topological and quantum-chemical descriptors selected with Genetic Algorithms in order to determine which of these parameters are responsible of the observed DPPH• radical scavenging activity. We constructed a back propagation neural network with the hydrophilic factor (Hy) descriptor to generate an adequate architecture of neurons for the system description. The mathematical model showed a multiple determination coefficient of 0.9196 and a root mean squared error of 0.0851. Our results shows that the presence of hydroxyl groups on the ring structure of 3-carboxy-coumarins are correlated with the observed DPPH• radical scavenging activity effects.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules171214882</identifier><identifier>PMID: 23519260</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Algorithms ; Antioxidants ; Benzopyrans - chemical synthesis ; Benzopyrans - pharmacology ; Biological activity ; Biphenyl Compounds - chemistry ; Computational Biology ; Coumarins - chemical synthesis ; Coumarins - chemistry ; Coumarins - pharmacology ; Electronic mail systems ; Free Radical Scavengers - chemical synthesis ; Free Radical Scavengers - pharmacology ; Models, Theoretical ; Neural networks ; Picrates - chemistry ; Product development ; Quantitative Structure-Activity Relationship ; Regression analysis</subject><ispartof>Molecules (Basel, Switzerland), 2012-12, Vol.17 (12), p.14882-14898</ispartof><rights>Copyright MDPI AG 2012</rights><rights>2012 by the authors; 2012</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c430t-5bef927647ea4e314b2291e5211db9f11c3af370ac493b453fb758c7746721293</citedby><cites>FETCH-LOGICAL-c430t-5bef927647ea4e314b2291e5211db9f11c3af370ac493b453fb758c7746721293</cites><orcidid>0000-0001-6951-9837</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268866/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268866/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23519260$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Martínez-Martínez, Francisco J</creatorcontrib><creatorcontrib>Razo-Hernández, Rodrigo Said</creatorcontrib><creatorcontrib>Peraza-Campos, Ana Lilia</creatorcontrib><creatorcontrib>Villanueva-García, Manuel</creatorcontrib><creatorcontrib>Sumaya-Martínez, Maria Teresa</creatorcontrib><creatorcontrib>Cano, Daniel Jaramillo</creatorcontrib><creatorcontrib>Gómez-Sandoval, Zeferino</creatorcontrib><title>Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and QSAR study of their DPPH• radical scavenging activity</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>The in vitro antioxidant activities of eight 3-carboxycoumarin derivatives were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazil (DPPH•) radical scavenging activity method. 3-Acetyl-6-hydroxy-2H-1-benzopyran-2-one (C1) and ethyl 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate (C2) presented the best radical-scavenging activity. A quantitative structure-activity relationship (QSAR) study was performed and correlated with the experimental DPPH• scavenging data. We used structural, geometrical, topological and quantum-chemical descriptors selected with Genetic Algorithms in order to determine which of these parameters are responsible of the observed DPPH• radical scavenging activity. We constructed a back propagation neural network with the hydrophilic factor (Hy) descriptor to generate an adequate architecture of neurons for the system description. The mathematical model showed a multiple determination coefficient of 0.9196 and a root mean squared error of 0.0851. Our results shows that the presence of hydroxyl groups on the ring structure of 3-carboxy-coumarins are correlated with the observed DPPH• radical scavenging activity effects.</description><subject>Algorithms</subject><subject>Antioxidants</subject><subject>Benzopyrans - chemical synthesis</subject><subject>Benzopyrans - pharmacology</subject><subject>Biological activity</subject><subject>Biphenyl Compounds - chemistry</subject><subject>Computational Biology</subject><subject>Coumarins - chemical synthesis</subject><subject>Coumarins - chemistry</subject><subject>Coumarins - pharmacology</subject><subject>Electronic mail systems</subject><subject>Free Radical Scavengers - chemical synthesis</subject><subject>Free Radical Scavengers - pharmacology</subject><subject>Models, Theoretical</subject><subject>Neural networks</subject><subject>Picrates - chemistry</subject><subject>Product development</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>Regression analysis</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNplkc1u1TAQhS0EoqXwAiyQJTZsUjz-ieMNUlV-ilSJlsLachzn1lWuXewkana8A2_Ao_Ek9dUtVy2sxvZ854xHB6GXQA4ZU-TtOg7OToPLIIECbxr6CO0Dp6RihKvH98576FnOV4QUCsRTtEeZAEVrso9-XSxhvHTZZ2xCh33Asx9TLJfRxxvflYqNHX15XbCbzTCZ0gg49phV1qQ23iw2TmuTirRzyc-lP7ut2_nF0Vecx6lbNnwZ4xN-f3Z28ufnb5xM560ZcLZmdmHlw2o35zl60pshuxd39QB9__jh2_FJdfrl0-fjo9PKckbGSrSuV1TWXDrDHQPeUqrACQrQtaoHsMz0TBJjuWItF6xvpWislLyWFKhiB-jd1vd6ateusy6MyQz6OvmyzqKj8fphJ_hLvYqzrmndNHVdDN7cGaT4Y3J51GufrRsGE1ycsgYGChoBkhT09T_oVZxSKOtpEAVjTS02FN1SNsWck-t3nwGiN5nr_zMvolf319hJ_obMbgGeTq4E</recordid><startdate>20121213</startdate><enddate>20121213</enddate><creator>Martínez-Martínez, Francisco J</creator><creator>Razo-Hernández, Rodrigo Said</creator><creator>Peraza-Campos, Ana Lilia</creator><creator>Villanueva-García, Manuel</creator><creator>Sumaya-Martínez, Maria Teresa</creator><creator>Cano, Daniel Jaramillo</creator><creator>Gómez-Sandoval, Zeferino</creator><general>MDPI AG</general><general>MDPI</general><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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-6951-9837</orcidid></search><sort><creationdate>20121213</creationdate><title>Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and QSAR study of their DPPH• radical scavenging activity</title><author>Martínez-Martínez, Francisco J ; Razo-Hernández, Rodrigo Said ; Peraza-Campos, Ana Lilia ; Villanueva-García, Manuel ; Sumaya-Martínez, Maria Teresa ; Cano, Daniel Jaramillo ; Gómez-Sandoval, Zeferino</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c430t-5bef927647ea4e314b2291e5211db9f11c3af370ac493b453fb758c7746721293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Algorithms</topic><topic>Antioxidants</topic><topic>Benzopyrans - chemical synthesis</topic><topic>Benzopyrans - pharmacology</topic><topic>Biological activity</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Computational Biology</topic><topic>Coumarins - chemical synthesis</topic><topic>Coumarins - chemistry</topic><topic>Coumarins - pharmacology</topic><topic>Electronic mail systems</topic><topic>Free Radical Scavengers - chemical synthesis</topic><topic>Free Radical Scavengers - pharmacology</topic><topic>Models, Theoretical</topic><topic>Neural networks</topic><topic>Picrates - chemistry</topic><topic>Product development</topic><topic>Quantitative Structure-Activity Relationship</topic><topic>Regression analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Martínez-Martínez, Francisco J</creatorcontrib><creatorcontrib>Razo-Hernández, Rodrigo Said</creatorcontrib><creatorcontrib>Peraza-Campos, Ana Lilia</creatorcontrib><creatorcontrib>Villanueva-García, Manuel</creatorcontrib><creatorcontrib>Sumaya-Martínez, Maria Teresa</creatorcontrib><creatorcontrib>Cano, Daniel Jaramillo</creatorcontrib><creatorcontrib>Gómez-Sandoval, Zeferino</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Martínez-Martínez, Francisco J</au><au>Razo-Hernández, Rodrigo Said</au><au>Peraza-Campos, Ana Lilia</au><au>Villanueva-García, Manuel</au><au>Sumaya-Martínez, Maria Teresa</au><au>Cano, Daniel Jaramillo</au><au>Gómez-Sandoval, Zeferino</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and QSAR study of their DPPH• radical scavenging activity</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2012-12-13</date><risdate>2012</risdate><volume>17</volume><issue>12</issue><spage>14882</spage><epage>14898</epage><pages>14882-14898</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>The in vitro antioxidant activities of eight 3-carboxycoumarin derivatives were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazil (DPPH•) radical scavenging activity method. 3-Acetyl-6-hydroxy-2H-1-benzopyran-2-one (C1) and ethyl 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate (C2) presented the best radical-scavenging activity. A quantitative structure-activity relationship (QSAR) study was performed and correlated with the experimental DPPH• scavenging data. We used structural, geometrical, topological and quantum-chemical descriptors selected with Genetic Algorithms in order to determine which of these parameters are responsible of the observed DPPH• radical scavenging activity. We constructed a back propagation neural network with the hydrophilic factor (Hy) descriptor to generate an adequate architecture of neurons for the system description. The mathematical model showed a multiple determination coefficient of 0.9196 and a root mean squared error of 0.0851. Our results shows that the presence of hydroxyl groups on the ring structure of 3-carboxy-coumarins are correlated with the observed DPPH• radical scavenging activity effects.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>23519260</pmid><doi>10.3390/molecules171214882</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0001-6951-9837</orcidid><oa>free_for_read</oa></addata></record> |
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| source | MDPI - Multidisciplinary Digital Publishing Institute; MEDLINE; DOAJ Directory of Open Access Journals; EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Algorithms Antioxidants Benzopyrans - chemical synthesis Benzopyrans - pharmacology Biological activity Biphenyl Compounds - chemistry Computational Biology Coumarins - chemical synthesis Coumarins - chemistry Coumarins - pharmacology Electronic mail systems Free Radical Scavengers - chemical synthesis Free Radical Scavengers - pharmacology Models, Theoretical Neural networks Picrates - chemistry Product development Quantitative Structure-Activity Relationship Regression analysis |
| title | Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and QSAR study of their DPPH• radical scavenging activity |
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