Novel Aminomethyl Derivatives of 4‐Methyl‐2‐prenylphenol: Synthesis and Antioxidant Properties
4‐Methyl‐2‐prenylphenol (1) was synthesized from para‐cresol and prenol, natural alcohol under the conditions of heterogeneous catalysis. A series of nine new aminomethyl derivatives with secondary and tertiary amino groups were obtained on the basis of compound 1. A comparative evaluation of their...
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| Veröffentlicht in: | Chemistry & biodiversity 2019-03, Vol.16 (3), p.e1800637-n/a |
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| creator | Buravlev, Evgeny V. Fedorova, Irina V. Shevchenko, Oksana G. Kutchin, Aleksandr V. |
| description | 4‐Methyl‐2‐prenylphenol (1) was synthesized from para‐cresol and prenol, natural alcohol under the conditions of heterogeneous catalysis. A series of nine new aminomethyl derivatives with secondary and tertiary amino groups were obtained on the basis of compound 1. A comparative evaluation of their antioxidant properties was carried out using in vitro models. It was established that Mannich base with octylaminomethyl group has radical‐scavenging activity, high Fe2+‐chelation ability as well as the ability to inhibit oxidative hemolysis of red blood cells. |
| doi_str_mv | 10.1002/cbdv.201800637 |
| format | Article |
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A series of nine new aminomethyl derivatives with secondary and tertiary amino groups were obtained on the basis of compound 1. A comparative evaluation of their antioxidant properties was carried out using in vitro models. It was established that Mannich base with octylaminomethyl group has radical‐scavenging activity, high Fe2+‐chelation ability as well as the ability to inhibit oxidative hemolysis of red blood cells.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.201800637</identifier><identifier>PMID: 30600917</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; alkylation ; Amino groups ; antioxidant activity ; Antioxidants ; Catalysis ; Chelation ; Cresol ; Derivatives ; Erythrocytes ; Iron ; Mannich bases ; oxidative hemolysis ; red blood cells ; Scavenging ; synthesis design</subject><ispartof>Chemistry & biodiversity, 2019-03, Vol.16 (3), p.e1800637-n/a</ispartof><rights>2019 Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2019 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3737-9badfa0dbb2da53813d6c7096b5d73f60455ec46a83029a550b4307d1515455f3</citedby><cites>FETCH-LOGICAL-c3737-9badfa0dbb2da53813d6c7096b5d73f60455ec46a83029a550b4307d1515455f3</cites><orcidid>0000-0002-7580-982X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.201800637$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.201800637$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30600917$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Buravlev, Evgeny V.</creatorcontrib><creatorcontrib>Fedorova, Irina V.</creatorcontrib><creatorcontrib>Shevchenko, Oksana G.</creatorcontrib><creatorcontrib>Kutchin, Aleksandr V.</creatorcontrib><title>Novel Aminomethyl Derivatives of 4‐Methyl‐2‐prenylphenol: Synthesis and Antioxidant Properties</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>4‐Methyl‐2‐prenylphenol (1) was synthesized from para‐cresol and prenol, natural alcohol under the conditions of heterogeneous catalysis. 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It was established that Mannich base with octylaminomethyl group has radical‐scavenging activity, high Fe2+‐chelation ability as well as the ability to inhibit oxidative hemolysis of red blood cells.</description><subject>Alcohols</subject><subject>alkylation</subject><subject>Amino groups</subject><subject>antioxidant activity</subject><subject>Antioxidants</subject><subject>Catalysis</subject><subject>Chelation</subject><subject>Cresol</subject><subject>Derivatives</subject><subject>Erythrocytes</subject><subject>Iron</subject><subject>Mannich bases</subject><subject>oxidative hemolysis</subject><subject>red blood cells</subject><subject>Scavenging</subject><subject>synthesis design</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkE1P3DAQhq2qqFDaa49VpF647DK2YzvpbVn6gQS0Uj-ukRNPtEaJHezsQm79CfxGfkkNS7dSLz2MZjTvM69GLyFvKMwpADtuarOZM6AFgOTqGTmgkrIZLQp4vpsV2ycvY7xKfNoXL8g-BwlQUnVAzKXfYJcteut8j-Nq6rJTDHajR7vBmPk2y-9_3V08KmlgqYaAbuqGFTrfvc--TW5cYbQx085kCzdaf2uNdmP2NfgBw2gxviJ7re4ivn7qh-THxw_fl59n518-nS0X57OGK65mZa1Nq8HUNTNa8IJyIxsFpayFUbyVkAuBTS51wYGVWgiocw7KUEFFklp-SI62vkPw12uMY9Xb2GDXaYd-HStGJVOKF7lM6Lt_0Cu_Di59l6gyFzlTBU_UfEs1wccYsK2GYHsdpopC9ZB_9ZB_tcs_Hbx9sl3XPZod_ifwBJRb4MZ2OP3HrlqenP78a_4bQKOUXw</recordid><startdate>201903</startdate><enddate>201903</enddate><creator>Buravlev, Evgeny V.</creator><creator>Fedorova, Irina V.</creator><creator>Shevchenko, Oksana G.</creator><creator>Kutchin, Aleksandr V.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7580-982X</orcidid></search><sort><creationdate>201903</creationdate><title>Novel Aminomethyl Derivatives of 4‐Methyl‐2‐prenylphenol: Synthesis and Antioxidant Properties</title><author>Buravlev, Evgeny V. ; Fedorova, Irina V. ; Shevchenko, Oksana G. ; Kutchin, Aleksandr V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3737-9badfa0dbb2da53813d6c7096b5d73f60455ec46a83029a550b4307d1515455f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alcohols</topic><topic>alkylation</topic><topic>Amino groups</topic><topic>antioxidant activity</topic><topic>Antioxidants</topic><topic>Catalysis</topic><topic>Chelation</topic><topic>Cresol</topic><topic>Derivatives</topic><topic>Erythrocytes</topic><topic>Iron</topic><topic>Mannich bases</topic><topic>oxidative hemolysis</topic><topic>red blood cells</topic><topic>Scavenging</topic><topic>synthesis design</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Buravlev, Evgeny V.</creatorcontrib><creatorcontrib>Fedorova, Irina V.</creatorcontrib><creatorcontrib>Shevchenko, Oksana G.</creatorcontrib><creatorcontrib>Kutchin, Aleksandr V.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Buravlev, Evgeny V.</au><au>Fedorova, Irina V.</au><au>Shevchenko, Oksana G.</au><au>Kutchin, Aleksandr V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Aminomethyl Derivatives of 4‐Methyl‐2‐prenylphenol: Synthesis and Antioxidant Properties</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2019-03</date><risdate>2019</risdate><volume>16</volume><issue>3</issue><spage>e1800637</spage><epage>n/a</epage><pages>e1800637-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>4‐Methyl‐2‐prenylphenol (1) was synthesized from para‐cresol and prenol, natural alcohol under the conditions of heterogeneous catalysis. A series of nine new aminomethyl derivatives with secondary and tertiary amino groups were obtained on the basis of compound 1. A comparative evaluation of their antioxidant properties was carried out using in vitro models. It was established that Mannich base with octylaminomethyl group has radical‐scavenging activity, high Fe2+‐chelation ability as well as the ability to inhibit oxidative hemolysis of red blood cells.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30600917</pmid><doi>10.1002/cbdv.201800637</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-7580-982X</orcidid></addata></record> |
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| identifier | ISSN: 1612-1872 |
| ispartof | Chemistry & biodiversity, 2019-03, Vol.16 (3), p.e1800637-n/a |
| issn | 1612-1872 1612-1880 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alcohols alkylation Amino groups antioxidant activity Antioxidants Catalysis Chelation Cresol Derivatives Erythrocytes Iron Mannich bases oxidative hemolysis red blood cells Scavenging synthesis design |
| title | Novel Aminomethyl Derivatives of 4‐Methyl‐2‐prenylphenol: Synthesis and Antioxidant Properties |
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