Design, Synthesis and Evaluation of Difunctionalized 4-Hydroxybenzaldehyde Derivatives as Novel Cholinesterase Inhibitors
A series of difunctionalized 4-hydroxybenzaldehyde derivatives were designed, synthesized and evaluated as cholinesterase (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)) inhibitors. The results demonstrated that all the compounds had more potent AChE and BChE inhibitory activities tha...
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2010/09/01, Vol.58(9), pp.1216-1220 |
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| container_title | Chemical & Pharmaceutical Bulletin |
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| creator | Yu, Liang Cao, Rihui Yi, Wei Yan, Qin Chen, Zhiyong Ma, Lin Song, Huacan |
| description | A series of difunctionalized 4-hydroxybenzaldehyde derivatives were designed, synthesized and evaluated as cholinesterase (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)) inhibitors. The results demonstrated that all the compounds had more potent AChE and BChE inhibitory activities than galanthamine-HBr, one of the best cholinesterase inhibitors known so far. The inhibition mechanism revealed that the best active compound 4e displayed a mix-type mode of AChE and BChE by its dual-site interactions with the catalytic triad active center and the peripheral anionic site (PAS) of enzyme. All these data suggested that further development of such compounds may be of interest. |
| doi_str_mv | 10.1248/cpb.58.1216 |
| format | Article |
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The results demonstrated that all the compounds had more potent AChE and BChE inhibitory activities than galanthamine-HBr, one of the best cholinesterase inhibitors known so far. The inhibition mechanism revealed that the best active compound 4e displayed a mix-type mode of AChE and BChE by its dual-site interactions with the catalytic triad active center and the peripheral anionic site (PAS) of enzyme. All these data suggested that further development of such compounds may be of interest.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.58.1216</identifier><identifier>PMID: 20823602</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>4-hydroxybenzaldehyde derivative ; Acetylcholinesterase - metabolism ; Animals ; Benzaldehydes - chemical synthesis ; Benzaldehydes - chemistry ; Benzaldehydes - pharmacology ; Butyrylcholinesterase - metabolism ; cholinesterase inhibitor ; Cholinesterase Inhibitors - chemical synthesis ; Cholinesterase Inhibitors - chemistry ; Cholinesterase Inhibitors - pharmacology ; Electrophorus ; Horses ; inhibition mechanism ; Molecular Structure ; synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2010/09/01, Vol.58(9), pp.1216-1220</ispartof><rights>2010 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c667t-ba125e8c8a26951942d5f3994650a5ad39b0c6a0f5ebcc6993bb13bba689dd0f3</citedby><cites>FETCH-LOGICAL-c667t-ba125e8c8a26951942d5f3994650a5ad39b0c6a0f5ebcc6993bb13bba689dd0f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20823602$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yu, Liang</creatorcontrib><creatorcontrib>Cao, Rihui</creatorcontrib><creatorcontrib>Yi, Wei</creatorcontrib><creatorcontrib>Yan, Qin</creatorcontrib><creatorcontrib>Chen, Zhiyong</creatorcontrib><creatorcontrib>Ma, Lin</creatorcontrib><creatorcontrib>Song, Huacan</creatorcontrib><creatorcontrib>Sun Yat-sen University</creatorcontrib><creatorcontrib>School of Chemistry and Chemical Engineering</creatorcontrib><title>Design, Synthesis and Evaluation of Difunctionalized 4-Hydroxybenzaldehyde Derivatives as Novel Cholinesterase Inhibitors</title><title>Chemical & Pharmaceutical Bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of difunctionalized 4-hydroxybenzaldehyde derivatives were designed, synthesized and evaluated as cholinesterase (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)) inhibitors. The results demonstrated that all the compounds had more potent AChE and BChE inhibitory activities than galanthamine-HBr, one of the best cholinesterase inhibitors known so far. The inhibition mechanism revealed that the best active compound 4e displayed a mix-type mode of AChE and BChE by its dual-site interactions with the catalytic triad active center and the peripheral anionic site (PAS) of enzyme. All these data suggested that further development of such compounds may be of interest.</description><subject>4-hydroxybenzaldehyde derivative</subject><subject>Acetylcholinesterase - metabolism</subject><subject>Animals</subject><subject>Benzaldehydes - chemical synthesis</subject><subject>Benzaldehydes - chemistry</subject><subject>Benzaldehydes - pharmacology</subject><subject>Butyrylcholinesterase - metabolism</subject><subject>cholinesterase inhibitor</subject><subject>Cholinesterase Inhibitors - chemical synthesis</subject><subject>Cholinesterase Inhibitors - chemistry</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Electrophorus</subject><subject>Horses</subject><subject>inhibition mechanism</subject><subject>Molecular Structure</subject><subject>synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU1v1DAQhiMEotvCiTuKxIEDpEz8lfhWtFvaShUcgLPlOJPGq6y92MmK9NfX220XiYPH4_Ez74w9WfauhPOSsPqL2TbnvE5-KV5ki5KyquCE0JfZAgBkQaigJ9lpjGsAwqGir7MTAnUKA1lk8wqjvXOf85-zG_vkx1y7Nr_c6WHSo_Uu912-st3kzP6kB3uPbc6K67kN_u_coLvXQ4v93GK-wmB3KWmHSSTm3_0Oh3zZ-8E6jCMGHTG_cb1t7OhDfJO96vQQ8e3Tfpb9_nb5a3ld3P64ull-vS2MENVYNLokHGtTayIkLyUjLe-olExw0Fy3VDZghIaOY2OMkJI2TZmWFrVsW-joWfbxoLsN_s-UGlEbGw0Og3bop6gqzoCwVCSRH_4j134K6c1RlUwAoyBqSNSnA2WCjzFgp7bBbnSYVQlqPxCVBqJ4rfYDSfT7J82p2WB7ZJ8nkICrA5BurdGDd_vv-lfZxMr0uLEpI-kD8BqkgpI_yieTwoQwVtGkdHFQWsdR3-GxlA6jNQM-tyUP5jH9eNXroNDRBxRvtVM</recordid><startdate>20100901</startdate><enddate>20100901</enddate><creator>Yu, Liang</creator><creator>Cao, Rihui</creator><creator>Yi, Wei</creator><creator>Yan, Qin</creator><creator>Chen, Zhiyong</creator><creator>Ma, Lin</creator><creator>Song, Huacan</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20100901</creationdate><title>Design, Synthesis and Evaluation of Difunctionalized 4-Hydroxybenzaldehyde Derivatives as Novel Cholinesterase Inhibitors</title><author>Yu, Liang ; Cao, Rihui ; Yi, Wei ; Yan, Qin ; Chen, Zhiyong ; Ma, Lin ; Song, Huacan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c667t-ba125e8c8a26951942d5f3994650a5ad39b0c6a0f5ebcc6993bb13bba689dd0f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>4-hydroxybenzaldehyde derivative</topic><topic>Acetylcholinesterase - metabolism</topic><topic>Animals</topic><topic>Benzaldehydes - chemical synthesis</topic><topic>Benzaldehydes - chemistry</topic><topic>Benzaldehydes - pharmacology</topic><topic>Butyrylcholinesterase - metabolism</topic><topic>cholinesterase inhibitor</topic><topic>Cholinesterase Inhibitors - chemical synthesis</topic><topic>Cholinesterase Inhibitors - chemistry</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Electrophorus</topic><topic>Horses</topic><topic>inhibition mechanism</topic><topic>Molecular Structure</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yu, Liang</creatorcontrib><creatorcontrib>Cao, Rihui</creatorcontrib><creatorcontrib>Yi, Wei</creatorcontrib><creatorcontrib>Yan, Qin</creatorcontrib><creatorcontrib>Chen, Zhiyong</creatorcontrib><creatorcontrib>Ma, Lin</creatorcontrib><creatorcontrib>Song, Huacan</creatorcontrib><creatorcontrib>Sun Yat-sen University</creatorcontrib><creatorcontrib>School of Chemistry and Chemical Engineering</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yu, Liang</au><au>Cao, Rihui</au><au>Yi, Wei</au><au>Yan, Qin</au><au>Chen, Zhiyong</au><au>Ma, Lin</au><au>Song, Huacan</au><aucorp>Sun Yat-sen University</aucorp><aucorp>School of Chemistry and Chemical Engineering</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis and Evaluation of Difunctionalized 4-Hydroxybenzaldehyde Derivatives as Novel Cholinesterase Inhibitors</atitle><jtitle>Chemical & Pharmaceutical Bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2010-09-01</date><risdate>2010</risdate><volume>58</volume><issue>9</issue><spage>1216</spage><epage>1220</epage><pages>1216-1220</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A series of difunctionalized 4-hydroxybenzaldehyde derivatives were designed, synthesized and evaluated as cholinesterase (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)) inhibitors. The results demonstrated that all the compounds had more potent AChE and BChE inhibitory activities than galanthamine-HBr, one of the best cholinesterase inhibitors known so far. The inhibition mechanism revealed that the best active compound 4e displayed a mix-type mode of AChE and BChE by its dual-site interactions with the catalytic triad active center and the peripheral anionic site (PAS) of enzyme. 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| subjects | 4-hydroxybenzaldehyde derivative Acetylcholinesterase - metabolism Animals Benzaldehydes - chemical synthesis Benzaldehydes - chemistry Benzaldehydes - pharmacology Butyrylcholinesterase - metabolism cholinesterase inhibitor Cholinesterase Inhibitors - chemical synthesis Cholinesterase Inhibitors - chemistry Cholinesterase Inhibitors - pharmacology Electrophorus Horses inhibition mechanism Molecular Structure synthesis |
| title | Design, Synthesis and Evaluation of Difunctionalized 4-Hydroxybenzaldehyde Derivatives as Novel Cholinesterase Inhibitors |
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