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
Hauptverfasser: Özil, Musa, Balaydın, Halis Türker, Şentürk, Murat
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Balaydın, Halis Türker
Şentürk, Murat
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.
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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 &amp; 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 &amp; 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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