Discovery of novel 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives as multifunctional MAO-B inhibitors for the treatment of Parkinson's disease
To discover novel multifunctional agents for the treatment of Parkinson's disease, a series of 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives was designed, synthesized and evaluated. The results revealed that representative compound 3h possessed potent and selective MAO-B inhib...
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| Veröffentlicht in: | Journal of enzyme inhibition and medicinal chemistry 2023-12, Vol.38 (1), p.2159957-2159957 |
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| creator | Cao, Zhongcheng Wang, Xingyue Zhang, Tianlong Fu, Xianwu Zhang, Fan Zhu, Jiang |
| description | To discover novel multifunctional agents for the treatment of Parkinson's disease, a series of 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives was designed, synthesized and evaluated. The results revealed that representative compound 3h possessed potent and selective MAO-B inhibitory activity (IC
50
= 0.062 µM), and its inhibitory mode was competitive and reversible. Additionally, 3h also displayed excellent anti-oxidative effect (ORAC = 2.27 Trolox equivalent), significant metal chelating ability and appropriate BBB permeability. Moreover, 3h exhibited good neuroprotective effect and anti-neuroinflammtory ability. These results indicated that compound 3h was a promising candidate for further development against PD. |
| doi_str_mv | 10.1080/14756366.2022.2159957 |
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50
= 0.062 µM), and its inhibitory mode was competitive and reversible. Additionally, 3h also displayed excellent anti-oxidative effect (ORAC = 2.27 Trolox equivalent), significant metal chelating ability and appropriate BBB permeability. Moreover, 3h exhibited good neuroprotective effect and anti-neuroinflammtory ability. These results indicated that compound 3h was a promising candidate for further development against PD.</description><identifier>ISSN: 1475-6366</identifier><identifier>EISSN: 1475-6374</identifier><identifier>DOI: 10.1080/14756366.2022.2159957</identifier><identifier>PMID: 36728713</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives ; Amine oxidase (flavin-containing) ; anti-neuroinflammatory agents ; Antioxidants ; Benzothiazole ; Benzothiazoles - pharmacology ; Contrast agents ; Design ; Dopamine ; Humans ; Hydrocarbons ; Hydroxyl Radical ; Laboratories ; MAO-B inhibitors ; Medical imaging ; Medical schools ; Membrane permeability ; Molecular Structure ; Monoamine Oxidase - metabolism ; Monoamine Oxidase Inhibitors - pharmacology ; Movement disorders ; multifunctional anti-PD agents ; Neurodegenerative diseases ; Neuroprotection ; Neuroprotective Agents - pharmacology ; Oxidative stress ; Parkinson Disease - drug therapy ; Parkinson's disease ; Permeability ; Pharmacy ; Research Paper ; Structure-Activity Relationship ; Tumor necrosis factor-TNF ; Vitamin E</subject><ispartof>Journal of enzyme inhibition and medicinal chemistry, 2023-12, Vol.38 (1), p.2159957-2159957</ispartof><rights>2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2023</rights><rights>2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. This work is licensed under the Creative Commons Attribution License http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2023 The Author(s)</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c562t-f015aad957a1607fd285a1ea3e086d3391808a2a04fa42766c967dc78f490a073</citedby><cites>FETCH-LOGICAL-c562t-f015aad957a1607fd285a1ea3e086d3391808a2a04fa42766c967dc78f490a073</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9897792/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9897792/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,2095,27481,27903,27904,53770,53772,59120,59121</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36728713$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cao, Zhongcheng</creatorcontrib><creatorcontrib>Wang, Xingyue</creatorcontrib><creatorcontrib>Zhang, Tianlong</creatorcontrib><creatorcontrib>Fu, Xianwu</creatorcontrib><creatorcontrib>Zhang, Fan</creatorcontrib><creatorcontrib>Zhu, Jiang</creatorcontrib><title>Discovery of novel 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives as multifunctional MAO-B inhibitors for the treatment of Parkinson's disease</title><title>Journal of enzyme inhibition and medicinal chemistry</title><addtitle>J Enzyme Inhib Med Chem</addtitle><description>To discover novel multifunctional agents for the treatment of Parkinson's disease, a series of 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives was designed, synthesized and evaluated. The results revealed that representative compound 3h possessed potent and selective MAO-B inhibitory activity (IC
50
= 0.062 µM), and its inhibitory mode was competitive and reversible. Additionally, 3h also displayed excellent anti-oxidative effect (ORAC = 2.27 Trolox equivalent), significant metal chelating ability and appropriate BBB permeability. Moreover, 3h exhibited good neuroprotective effect and anti-neuroinflammtory ability. These results indicated that compound 3h was a promising candidate for further development against PD.</description><subject>2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives</subject><subject>Amine oxidase (flavin-containing)</subject><subject>anti-neuroinflammatory agents</subject><subject>Antioxidants</subject><subject>Benzothiazole</subject><subject>Benzothiazoles - pharmacology</subject><subject>Contrast agents</subject><subject>Design</subject><subject>Dopamine</subject><subject>Humans</subject><subject>Hydrocarbons</subject><subject>Hydroxyl Radical</subject><subject>Laboratories</subject><subject>MAO-B inhibitors</subject><subject>Medical imaging</subject><subject>Medical schools</subject><subject>Membrane permeability</subject><subject>Molecular Structure</subject><subject>Monoamine Oxidase - metabolism</subject><subject>Monoamine Oxidase Inhibitors - pharmacology</subject><subject>Movement disorders</subject><subject>multifunctional anti-PD agents</subject><subject>Neurodegenerative diseases</subject><subject>Neuroprotection</subject><subject>Neuroprotective Agents - pharmacology</subject><subject>Oxidative stress</subject><subject>Parkinson Disease - drug therapy</subject><subject>Parkinson's disease</subject><subject>Permeability</subject><subject>Pharmacy</subject><subject>Research Paper</subject><subject>Structure-Activity Relationship</subject><subject>Tumor necrosis factor-TNF</subject><subject>Vitamin E</subject><issn>1475-6366</issn><issn>1475-6374</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>0YH</sourceid><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>DOA</sourceid><recordid>eNp9Uk1v1DAQjRCIlsJPAFniwPaQxXYcO74gSvmqVFQOcLYmsdP1krUX21nY_hn-Kg67XVEOnGY08-bN1yuKpwTPCW7wS8JEzSvO5xRTOqeklrIW94rjKV7ySrD7B5_zo-JRjEuMKaGEPSyOKi5oI0h1XPx6a2PnNyZske-Ry96AaDlj5aw17mY7-J_b07IuZ4utDtkfTtF6Ydxkp7xPCws3fjBIm2A3kOzGRAQRrcYh2X50XbLewYA-nV2Vb5B1C9va5ENEvQ8oLQxKwUBaGZem9p8hfLMuevciIm2jgWgeFw96GKJ5srcnxdf3776cfywvrz5cnJ9dll3NaSp7TGoAnU8AhGPRa9rUQAxUBjdcV5UkDW6AAmY9MCo47yQXuhNNzyQGLKqT4mLHqz0s1TrYFYSt8mDVn4AP1wpCst1gFG94DbgVfWcqxnDm0Mz0nGpo207qNnO92nGtx3ZldJe3CzDcIb2bcXahrv1GyUYKIWkmmO0Jgv8-mpjUKn_JDAM448eoqBBEsoo1MkOf_wNd-jHkk2eUJKJmknCWUfUO1QUfYzD9YRiC1SQndSsnNclJ7eWU6579vcmh6lY_GfB6B7Auf3QFP3wYtEqQhRP6AK6zUVX_7_Eb0pPcKA</recordid><startdate>202312</startdate><enddate>202312</enddate><creator>Cao, Zhongcheng</creator><creator>Wang, Xingyue</creator><creator>Zhang, Tianlong</creator><creator>Fu, Xianwu</creator><creator>Zhang, Fan</creator><creator>Zhu, Jiang</creator><general>Taylor & Francis</general><general>Taylor & Francis Ltd</general><general>Taylor & Francis Group</general><scope>0YH</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>3V.</scope><scope>7T5</scope><scope>7X7</scope><scope>7XB</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>H94</scope><scope>K9.</scope><scope>M0S</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>202312</creationdate><title>Discovery of novel 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives as multifunctional MAO-B inhibitors for the treatment of Parkinson's disease</title><author>Cao, Zhongcheng ; Wang, Xingyue ; Zhang, Tianlong ; Fu, Xianwu ; Zhang, Fan ; Zhu, Jiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c562t-f015aad957a1607fd285a1ea3e086d3391808a2a04fa42766c967dc78f490a073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives</topic><topic>Amine oxidase (flavin-containing)</topic><topic>anti-neuroinflammatory agents</topic><topic>Antioxidants</topic><topic>Benzothiazole</topic><topic>Benzothiazoles - pharmacology</topic><topic>Contrast agents</topic><topic>Design</topic><topic>Dopamine</topic><topic>Humans</topic><topic>Hydrocarbons</topic><topic>Hydroxyl Radical</topic><topic>Laboratories</topic><topic>MAO-B inhibitors</topic><topic>Medical imaging</topic><topic>Medical schools</topic><topic>Membrane permeability</topic><topic>Molecular Structure</topic><topic>Monoamine Oxidase - metabolism</topic><topic>Monoamine Oxidase Inhibitors - pharmacology</topic><topic>Movement disorders</topic><topic>multifunctional anti-PD agents</topic><topic>Neurodegenerative diseases</topic><topic>Neuroprotection</topic><topic>Neuroprotective Agents - pharmacology</topic><topic>Oxidative stress</topic><topic>Parkinson Disease - drug therapy</topic><topic>Parkinson's disease</topic><topic>Permeability</topic><topic>Pharmacy</topic><topic>Research Paper</topic><topic>Structure-Activity Relationship</topic><topic>Tumor necrosis factor-TNF</topic><topic>Vitamin E</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cao, Zhongcheng</creatorcontrib><creatorcontrib>Wang, Xingyue</creatorcontrib><creatorcontrib>Zhang, Tianlong</creatorcontrib><creatorcontrib>Fu, Xianwu</creatorcontrib><creatorcontrib>Zhang, Fan</creatorcontrib><creatorcontrib>Zhu, Jiang</creatorcontrib><collection>Taylor & Francis Open Access</collection><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>Immunology Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</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>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</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><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Journal of enzyme inhibition and medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cao, Zhongcheng</au><au>Wang, Xingyue</au><au>Zhang, Tianlong</au><au>Fu, Xianwu</au><au>Zhang, Fan</au><au>Zhu, Jiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of novel 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives as multifunctional MAO-B inhibitors for the treatment of Parkinson's disease</atitle><jtitle>Journal of enzyme inhibition and medicinal chemistry</jtitle><addtitle>J Enzyme Inhib Med Chem</addtitle><date>2023-12</date><risdate>2023</risdate><volume>38</volume><issue>1</issue><spage>2159957</spage><epage>2159957</epage><pages>2159957-2159957</pages><issn>1475-6366</issn><eissn>1475-6374</eissn><abstract>To discover novel multifunctional agents for the treatment of Parkinson's disease, a series of 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives was designed, synthesized and evaluated. The results revealed that representative compound 3h possessed potent and selective MAO-B inhibitory activity (IC
50
= 0.062 µM), and its inhibitory mode was competitive and reversible. Additionally, 3h also displayed excellent anti-oxidative effect (ORAC = 2.27 Trolox equivalent), significant metal chelating ability and appropriate BBB permeability. Moreover, 3h exhibited good neuroprotective effect and anti-neuroinflammtory ability. These results indicated that compound 3h was a promising candidate for further development against PD.</abstract><cop>England</cop><pub>Taylor & Francis</pub><pmid>36728713</pmid><doi>10.1080/14756366.2022.2159957</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives Amine oxidase (flavin-containing) anti-neuroinflammatory agents Antioxidants Benzothiazole Benzothiazoles - pharmacology Contrast agents Design Dopamine Humans Hydrocarbons Hydroxyl Radical Laboratories MAO-B inhibitors Medical imaging Medical schools Membrane permeability Molecular Structure Monoamine Oxidase - metabolism Monoamine Oxidase Inhibitors - pharmacology Movement disorders multifunctional anti-PD agents Neurodegenerative diseases Neuroprotection Neuroprotective Agents - pharmacology Oxidative stress Parkinson Disease - drug therapy Parkinson's disease Permeability Pharmacy Research Paper Structure-Activity Relationship Tumor necrosis factor-TNF Vitamin E |
| title | Discovery of novel 2-(4-(benzyloxy)-5-(hydroxyl) phenyl) benzothiazole derivatives as multifunctional MAO-B inhibitors for the treatment of Parkinson's disease |
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