New bis-catechols 5-lipoxygenase inhibitors
Three polyhydroxy-2-phenylnaphthalenes (1-3) and the oxy analogue of tetrahydroxypavinan (4) were prepared and evaluated for their antioxidant properties (inhibition of diphenylpycrylhydrazyl radical (DPPH), reduction of iron (III) ion) and inhibition of 5-lipoxygenase (5-LO) activity. Their three-d...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2001-02, Vol.9 (2), p.229-235 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | DUPONT, Romain GOOSSENS, Jean-Francois COTELLE, Nicole VRIELYNCK, Laurence VEZIN, Hervé HENICHART, Jean-Pierre COTELLE, Philippe |
| description | Three polyhydroxy-2-phenylnaphthalenes (1-3) and the oxy analogue of tetrahydroxypavinan (4) were prepared and evaluated for their antioxidant properties (inhibition of diphenylpycrylhydrazyl radical (DPPH), reduction of iron (III) ion) and inhibition of 5-lipoxygenase (5-LO) activity. Their three-dimensional structures were established on the basis of spectroscopic data and semiempirical calculations. Compounds 1 and 2 were found as potent 5-LO inhibitors as nordihydroguaiaretic acid (NDGA), whereas 4 is 2.5 times less potent than NDGA. The reliability of the 3-D structures with the 5-LO inhibition properties is discussed. Their antioxidant properties show that tested compounds are expected to act as redox inhibitors. |
| doi_str_mv | 10.1016/S0968-0896(00)00258-3 |
| format | Article |
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Their three-dimensional structures were established on the basis of spectroscopic data and semiempirical calculations. Compounds 1 and 2 were found as potent 5-LO inhibitors as nordihydroguaiaretic acid (NDGA), whereas 4 is 2.5 times less potent than NDGA. The reliability of the 3-D structures with the 5-LO inhibition properties is discussed. Their antioxidant properties show that tested compounds are expected to act as redox inhibitors.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/S0968-0896(00)00258-3</identifier><identifier>PMID: 11249115</identifier><language>eng</language><publisher>Oxford: Elsevier Science</publisher><subject>Animals ; Antioxidants - chemical synthesis ; Antioxidants - pharmacology ; Arachidonate 5-Lipoxygenase - drug effects ; Arachidonate 5-Lipoxygenase - metabolism ; Bepridil - analogs & derivatives ; Bepridil - metabolism ; Biological and medical sciences ; Biphenyl Compounds ; Bones, joints and connective tissue. Antiinflammatory agents ; Catechols ; General and cellular metabolism. Vitamins ; Indicators and Reagents ; Iron - metabolism ; Kinetics ; Lipoxygenase Inhibitors - chemical synthesis ; Lipoxygenase Inhibitors - pharmacology ; Medical sciences ; Molecular Structure ; Oxidation-Reduction ; Pharmacology. Drug treatments ; Picrates ; Rats ; Structure-Activity Relationship ; Tumor Cells, Cultured</subject><ispartof>Bioorganic & medicinal chemistry, 2001-02, Vol.9 (2), p.229-235</ispartof><rights>2001 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c367t-2992daa20fc366951a8106b8d8c06ee4c4022583e9c8c1d38efbc98ef919f2ed3</citedby><cites>FETCH-LOGICAL-c367t-2992daa20fc366951a8106b8d8c06ee4c4022583e9c8c1d38efbc98ef919f2ed3</cites><orcidid>0000-0002-7282-2703</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,778,782,883,27911,27912</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=894969$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11249115$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00279877$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>DUPONT, Romain</creatorcontrib><creatorcontrib>GOOSSENS, Jean-Francois</creatorcontrib><creatorcontrib>COTELLE, Nicole</creatorcontrib><creatorcontrib>VRIELYNCK, Laurence</creatorcontrib><creatorcontrib>VEZIN, Hervé</creatorcontrib><creatorcontrib>HENICHART, Jean-Pierre</creatorcontrib><creatorcontrib>COTELLE, Philippe</creatorcontrib><title>New bis-catechols 5-lipoxygenase inhibitors</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Three polyhydroxy-2-phenylnaphthalenes (1-3) and the oxy analogue of tetrahydroxypavinan (4) were prepared and evaluated for their antioxidant properties (inhibition of diphenylpycrylhydrazyl radical (DPPH), reduction of iron (III) ion) and inhibition of 5-lipoxygenase (5-LO) activity. Their three-dimensional structures were established on the basis of spectroscopic data and semiempirical calculations. Compounds 1 and 2 were found as potent 5-LO inhibitors as nordihydroguaiaretic acid (NDGA), whereas 4 is 2.5 times less potent than NDGA. The reliability of the 3-D structures with the 5-LO inhibition properties is discussed. Their antioxidant properties show that tested compounds are expected to act as redox inhibitors.</description><subject>Animals</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - pharmacology</subject><subject>Arachidonate 5-Lipoxygenase - drug effects</subject><subject>Arachidonate 5-Lipoxygenase - metabolism</subject><subject>Bepridil - analogs & derivatives</subject><subject>Bepridil - metabolism</subject><subject>Biological and medical sciences</subject><subject>Biphenyl Compounds</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Catechols</subject><subject>General and cellular metabolism. Vitamins</subject><subject>Indicators and Reagents</subject><subject>Iron - metabolism</subject><subject>Kinetics</subject><subject>Lipoxygenase Inhibitors - chemical synthesis</subject><subject>Lipoxygenase Inhibitors - pharmacology</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Pharmacology. Drug treatments</subject><subject>Picrates</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkF1LwzAUQIMobk5_gjIQxCHRpGnT3Mcx1AlDH9TnkKa3LtKts-nU_XvTrcyXJDec-3UIOefsljMu714ZSEWZAnnN2IixKFFUHJA-j2VMhQB-SPp7pEdOvP9kgYqBH5Me5-2DJ31y84w_w8x5ak2Ddl6VfpjQ0q2q380HLo3HoVvOXeaaqvan5Kgwpcez7h6Q94f7t8mUzl4enybjGbVCpg2NAKLcmIgVIZaQcKM4k5nKlWUSMbYxi8K0AsEqy3OhsMgshBM4FBHmYkBGu7pzU-pV7Ram3ujKOD0dz3T7F_ZIQaXpNw_s1Y5d1dXXGn2jF85bLEuzxGrtdSpBJmnUgskOtHXlfY3FvjJnujWqt0Z1qys00FujWoS8i67BOltg_p_VKQzAZQcYb01Z1GZpnd9zCmKQIP4A3QZ76Q</recordid><startdate>20010201</startdate><enddate>20010201</enddate><creator>DUPONT, Romain</creator><creator>GOOSSENS, Jean-Francois</creator><creator>COTELLE, Nicole</creator><creator>VRIELYNCK, Laurence</creator><creator>VEZIN, Hervé</creator><creator>HENICHART, Jean-Pierre</creator><creator>COTELLE, Philippe</creator><general>Elsevier Science</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>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-7282-2703</orcidid></search><sort><creationdate>20010201</creationdate><title>New bis-catechols 5-lipoxygenase inhibitors</title><author>DUPONT, Romain ; GOOSSENS, Jean-Francois ; COTELLE, Nicole ; VRIELYNCK, Laurence ; VEZIN, Hervé ; HENICHART, Jean-Pierre ; COTELLE, Philippe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c367t-2992daa20fc366951a8106b8d8c06ee4c4022583e9c8c1d38efbc98ef919f2ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Animals</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - pharmacology</topic><topic>Arachidonate 5-Lipoxygenase - drug effects</topic><topic>Arachidonate 5-Lipoxygenase - metabolism</topic><topic>Bepridil - analogs & derivatives</topic><topic>Bepridil - metabolism</topic><topic>Biological and medical sciences</topic><topic>Biphenyl Compounds</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Catechols</topic><topic>General and cellular metabolism. Vitamins</topic><topic>Indicators and Reagents</topic><topic>Iron - metabolism</topic><topic>Kinetics</topic><topic>Lipoxygenase Inhibitors - chemical synthesis</topic><topic>Lipoxygenase Inhibitors - pharmacology</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Pharmacology. Drug treatments</topic><topic>Picrates</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>DUPONT, Romain</creatorcontrib><creatorcontrib>GOOSSENS, Jean-Francois</creatorcontrib><creatorcontrib>COTELLE, Nicole</creatorcontrib><creatorcontrib>VRIELYNCK, Laurence</creatorcontrib><creatorcontrib>VEZIN, Hervé</creatorcontrib><creatorcontrib>HENICHART, Jean-Pierre</creatorcontrib><creatorcontrib>COTELLE, Philippe</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><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>DUPONT, Romain</au><au>GOOSSENS, Jean-Francois</au><au>COTELLE, Nicole</au><au>VRIELYNCK, Laurence</au><au>VEZIN, Hervé</au><au>HENICHART, Jean-Pierre</au><au>COTELLE, Philippe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New bis-catechols 5-lipoxygenase inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2001-02-01</date><risdate>2001</risdate><volume>9</volume><issue>2</issue><spage>229</spage><epage>235</epage><pages>229-235</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Three polyhydroxy-2-phenylnaphthalenes (1-3) and the oxy analogue of tetrahydroxypavinan (4) were prepared and evaluated for their antioxidant properties (inhibition of diphenylpycrylhydrazyl radical (DPPH), reduction of iron (III) ion) and inhibition of 5-lipoxygenase (5-LO) activity. Their three-dimensional structures were established on the basis of spectroscopic data and semiempirical calculations. Compounds 1 and 2 were found as potent 5-LO inhibitors as nordihydroguaiaretic acid (NDGA), whereas 4 is 2.5 times less potent than NDGA. The reliability of the 3-D structures with the 5-LO inhibition properties is discussed. Their antioxidant properties show that tested compounds are expected to act as redox inhibitors.</abstract><cop>Oxford</cop><pub>Elsevier Science</pub><pmid>11249115</pmid><doi>10.1016/S0968-0896(00)00258-3</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-7282-2703</orcidid></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2001-02, Vol.9 (2), p.229-235 |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Animals Antioxidants - chemical synthesis Antioxidants - pharmacology Arachidonate 5-Lipoxygenase - drug effects Arachidonate 5-Lipoxygenase - metabolism Bepridil - analogs & derivatives Bepridil - metabolism Biological and medical sciences Biphenyl Compounds Bones, joints and connective tissue. Antiinflammatory agents Catechols General and cellular metabolism. Vitamins Indicators and Reagents Iron - metabolism Kinetics Lipoxygenase Inhibitors - chemical synthesis Lipoxygenase Inhibitors - pharmacology Medical sciences Molecular Structure Oxidation-Reduction Pharmacology. Drug treatments Picrates Rats Structure-Activity Relationship Tumor Cells, Cultured |
| title | New bis-catechols 5-lipoxygenase inhibitors |
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