Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties
[Display omitted] •Synthesis of triazole derivatives by using microwave and conventional method.•Isomers and conformers studied of new molecules.•Carbonic anhydrase and cholinesterase inhibitory properties.•Identification of a new class of inhibitors.•Structure Activity Relationship established. Car...
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Veröffentlicht in: | Bioorganic chemistry 2019-05, Vol.86, p.705-713 |
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•Synthesis of triazole derivatives by using microwave and conventional method.•Isomers and conformers studied of new molecules.•Carbonic anhydrase and cholinesterase inhibitory properties.•Identification of a new class of inhibitors.•Structure Activity Relationship established.
Carbonic anhydrase enzymes (EC 4.2.1.1, CAs) are metalloenzyme families that catalyze the rapid conversion of H2O and CO2 to HCO3– and H+. CAs are found in different tissues where they participate in various significant biochemical processes such as ion transport, carbon dioxide respiration, ureagenesis, lipogenesis, bone resorption, electrolyte secretion, acid-base balance, and gluconeogenesis. In such processes, many CAs are significant therapeutic targets because of their inhibitory potentials especially in the treatment of some diseases such as edema, glaucoma, obesity, cancer, epilepsy, and osteoporosis. Acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) inhibitors are also valuable compounds for different therapeutic applications including Alzheimer’s disease. In this work, we report a fast and effective synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and also their CA and cholinesterases inhibitory properties. Our findings showed that these Schiff base derivatives, with triazole ring, found as strong CA and cholinesterases inhibitors. |
doi_str_mv | 10.1016/j.bioorg.2019.02.045 |
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•Synthesis of triazole derivatives by using microwave and conventional method.•Isomers and conformers studied of new molecules.•Carbonic anhydrase and cholinesterase inhibitory properties.•Identification of a new class of inhibitors.•Structure Activity Relationship established.
Carbonic anhydrase enzymes (EC 4.2.1.1, CAs) are metalloenzyme families that catalyze the rapid conversion of H2O and CO2 to HCO3– and H+. CAs are found in different tissues where they participate in various significant biochemical processes such as ion transport, carbon dioxide respiration, ureagenesis, lipogenesis, bone resorption, electrolyte secretion, acid-base balance, and gluconeogenesis. In such processes, many CAs are significant therapeutic targets because of their inhibitory potentials especially in the treatment of some diseases such as edema, glaucoma, obesity, cancer, epilepsy, and osteoporosis. Acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) inhibitors are also valuable compounds for different therapeutic applications including Alzheimer’s disease. In this work, we report a fast and effective synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and also their CA and cholinesterases inhibitory properties. Our findings showed that these Schiff base derivatives, with triazole ring, found as strong CA and cholinesterases inhibitors.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2019.02.045</identifier><identifier>PMID: 30836234</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>1,2,4-Triazole ; Acetylcholinesterase - metabolism ; Animals ; Benzohydrazide ; Butyrylcholinesterase - metabolism ; Carbonic anhydrase ; Carbonic Anhydrase Inhibitors - chemical synthesis ; Carbonic Anhydrase Inhibitors - chemistry ; Carbonic Anhydrase Inhibitors - pharmacology ; Carbonic Anhydrases - metabolism ; Cholinesterase ; Cholinesterase Inhibitors - chemical synthesis ; Cholinesterase Inhibitors - chemistry ; Cholinesterase Inhibitors - pharmacology ; Dose-Response Relationship, Drug ; Electrophorus ; Enzyme inhibition ; Horses ; Humans ; Isoenzymes - antagonists & inhibitors ; Isoenzymes - metabolism ; Microwaves ; Molecular Structure ; Schiff base ; Schiff Bases - chemical synthesis ; Schiff Bases - chemistry ; Schiff Bases - pharmacology ; Structure-Activity Relationship ; Triazoles - chemical synthesis ; Triazoles - chemistry ; Triazoles - pharmacology</subject><ispartof>Bioorganic chemistry, 2019-05, Vol.86, p.705-713</ispartof><rights>2019 Elsevier Inc.</rights><rights>Copyright © 2019 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-e40f85bc3c527e2048cef2b429cf21d192e06fecf92779593e5e9d47559fec863</citedby><cites>FETCH-LOGICAL-c362t-e40f85bc3c527e2048cef2b429cf21d192e06fecf92779593e5e9d47559fec863</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0045206818313439$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30836234$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Özil, Musa</creatorcontrib><creatorcontrib>Balaydın, Halis Türker</creatorcontrib><creatorcontrib>Şentürk, Murat</creatorcontrib><title>Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties</title><title>Bioorganic chemistry</title><addtitle>Bioorg Chem</addtitle><description>[Display omitted]
•Synthesis of triazole derivatives by using microwave and conventional method.•Isomers and conformers studied of new molecules.•Carbonic anhydrase and cholinesterase inhibitory properties.•Identification of a new class of inhibitors.•Structure Activity Relationship established.
Carbonic anhydrase enzymes (EC 4.2.1.1, CAs) are metalloenzyme families that catalyze the rapid conversion of H2O and CO2 to HCO3– and H+. CAs are found in different tissues where they participate in various significant biochemical processes such as ion transport, carbon dioxide respiration, ureagenesis, lipogenesis, bone resorption, electrolyte secretion, acid-base balance, and gluconeogenesis. In such processes, many CAs are significant therapeutic targets because of their inhibitory potentials especially in the treatment of some diseases such as edema, glaucoma, obesity, cancer, epilepsy, and osteoporosis. Acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) inhibitors are also valuable compounds for different therapeutic applications including Alzheimer’s disease. In this work, we report a fast and effective synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and also their CA and cholinesterases inhibitory properties. Our findings showed that these Schiff base derivatives, with triazole ring, found as strong CA and cholinesterases inhibitors.</description><subject>1,2,4-Triazole</subject><subject>Acetylcholinesterase - metabolism</subject><subject>Animals</subject><subject>Benzohydrazide</subject><subject>Butyrylcholinesterase - metabolism</subject><subject>Carbonic anhydrase</subject><subject>Carbonic Anhydrase Inhibitors - chemical synthesis</subject><subject>Carbonic Anhydrase Inhibitors - chemistry</subject><subject>Carbonic Anhydrase Inhibitors - pharmacology</subject><subject>Carbonic Anhydrases - metabolism</subject><subject>Cholinesterase</subject><subject>Cholinesterase Inhibitors - chemical synthesis</subject><subject>Cholinesterase Inhibitors - chemistry</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Electrophorus</subject><subject>Enzyme inhibition</subject><subject>Horses</subject><subject>Humans</subject><subject>Isoenzymes - antagonists & inhibitors</subject><subject>Isoenzymes - metabolism</subject><subject>Microwaves</subject><subject>Molecular Structure</subject><subject>Schiff base</subject><subject>Schiff Bases - chemical synthesis</subject><subject>Schiff Bases - chemistry</subject><subject>Schiff Bases - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - pharmacology</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UcFu1DAQtRCILoU_QCjHIq2D7dhJfEEqq0KRKnEonK3EGTezysaLnV0pnPiNfkp_hy_BYQtHTmO9eW_ejB8hrznLOePlu23eovfhLheM65yJnEn1hKw404wKLthTsmIJooKV9Rl5EeOWMc5lVT4nZwWri1IUckUebudx6iFizLzLFN3B1M8DFWtJO-znLnhaXFO-XoApYPPDD0AL6kf49fM-Zk2Yh-zW9uhc1jYRsg4CHpsJj5CaY5fhmF4T3iXIj4uFbULrR7Spu4xfNAvP9n7AMVHhD3Rxuemv1tmHQypv05AeW5x8mLN98HsIE0J8SZ65Zojw6rGek28fr75urunNl0-fN5c31KYTJwqSuVq1trBKVCCYrC040UqhrRO841oAKx1Yp0VVaaULUKA7WSmlE1qXxTm5OM1N1t8PaUOzw2hhGJoR_CEawetaac6UTFR5otrgYwzgzD7gLv2R4cwsoZmtOYVmltAMEyYllGRvHh0O7Q66f6K_KSXC-xMB0p1HhGCiRRgtdBjATqbz-H-H3-5irK4</recordid><startdate>201905</startdate><enddate>201905</enddate><creator>Özil, Musa</creator><creator>Balaydın, Halis Türker</creator><creator>Şentürk, Murat</creator><general>Elsevier Inc</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>7X8</scope></search><sort><creationdate>201905</creationdate><title>Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties</title><author>Özil, Musa ; Balaydın, Halis Türker ; Şentürk, Murat</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-e40f85bc3c527e2048cef2b429cf21d192e06fecf92779593e5e9d47559fec863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>1,2,4-Triazole</topic><topic>Acetylcholinesterase - metabolism</topic><topic>Animals</topic><topic>Benzohydrazide</topic><topic>Butyrylcholinesterase - metabolism</topic><topic>Carbonic anhydrase</topic><topic>Carbonic Anhydrase Inhibitors - chemical synthesis</topic><topic>Carbonic Anhydrase Inhibitors - chemistry</topic><topic>Carbonic Anhydrase Inhibitors - pharmacology</topic><topic>Carbonic Anhydrases - metabolism</topic><topic>Cholinesterase</topic><topic>Cholinesterase Inhibitors - chemical synthesis</topic><topic>Cholinesterase Inhibitors - chemistry</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Electrophorus</topic><topic>Enzyme inhibition</topic><topic>Horses</topic><topic>Humans</topic><topic>Isoenzymes - antagonists & inhibitors</topic><topic>Isoenzymes - metabolism</topic><topic>Microwaves</topic><topic>Molecular Structure</topic><topic>Schiff base</topic><topic>Schiff Bases - chemical synthesis</topic><topic>Schiff Bases - chemistry</topic><topic>Schiff Bases - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Triazoles - chemical synthesis</topic><topic>Triazoles - chemistry</topic><topic>Triazoles - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Özil, Musa</creatorcontrib><creatorcontrib>Balaydın, Halis Türker</creatorcontrib><creatorcontrib>Şentürk, Murat</creatorcontrib><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><jtitle>Bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Özil, Musa</au><au>Balaydın, Halis Türker</au><au>Şentürk, Murat</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties</atitle><jtitle>Bioorganic chemistry</jtitle><addtitle>Bioorg Chem</addtitle><date>2019-05</date><risdate>2019</risdate><volume>86</volume><spage>705</spage><epage>713</epage><pages>705-713</pages><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>[Display omitted]
•Synthesis of triazole derivatives by using microwave and conventional method.•Isomers and conformers studied of new molecules.•Carbonic anhydrase and cholinesterase inhibitory properties.•Identification of a new class of inhibitors.•Structure Activity Relationship established.
Carbonic anhydrase enzymes (EC 4.2.1.1, CAs) are metalloenzyme families that catalyze the rapid conversion of H2O and CO2 to HCO3– and H+. CAs are found in different tissues where they participate in various significant biochemical processes such as ion transport, carbon dioxide respiration, ureagenesis, lipogenesis, bone resorption, electrolyte secretion, acid-base balance, and gluconeogenesis. In such processes, many CAs are significant therapeutic targets because of their inhibitory potentials especially in the treatment of some diseases such as edema, glaucoma, obesity, cancer, epilepsy, and osteoporosis. Acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) inhibitors are also valuable compounds for different therapeutic applications including Alzheimer’s disease. In this work, we report a fast and effective synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and also their CA and cholinesterases inhibitory properties. Our findings showed that these Schiff base derivatives, with triazole ring, found as strong CA and cholinesterases inhibitors.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>30836234</pmid><doi>10.1016/j.bioorg.2019.02.045</doi><tpages>9</tpages></addata></record> |
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subjects | 1,2,4-Triazole Acetylcholinesterase - metabolism Animals Benzohydrazide Butyrylcholinesterase - metabolism Carbonic anhydrase Carbonic Anhydrase Inhibitors - chemical synthesis Carbonic Anhydrase Inhibitors - chemistry Carbonic Anhydrase Inhibitors - pharmacology Carbonic Anhydrases - metabolism Cholinesterase Cholinesterase Inhibitors - chemical synthesis Cholinesterase Inhibitors - chemistry Cholinesterase Inhibitors - pharmacology Dose-Response Relationship, Drug Electrophorus Enzyme inhibition Horses Humans Isoenzymes - antagonists & inhibitors Isoenzymes - metabolism Microwaves Molecular Structure Schiff base Schiff Bases - chemical synthesis Schiff Bases - chemistry Schiff Bases - pharmacology Structure-Activity Relationship Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology |
title | Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties |
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