Synthesis, characterization and biological screening of sulfonamides derived form 2-phenylethylamine
In the present study, a series of N-substituted derivatives of 2-phenylethylamine has been synthesized. The reaction of 2-phenylethylamine (1) with benzene sulfonyl chloride (2) yielded N-(2-phenylethyl) benzenesulfonamide (3), which further on treatment with alkyl/acyl halides (4a-i) in the presenc...
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| Veröffentlicht in: | Pakistan journal of pharmaceutical sciences 2012-10, Vol.25 (4), p.809-814 |
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| container_title | Pakistan journal of pharmaceutical sciences |
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| creator | Rehman, Aziz-ur Afroz, Sumbel Abbasi, Muhammad Athar Tanveer, Wajeeha Khan, Khalid Mohammed Ashraf, Muhammad Ahmad, Irshad Afzal, Iftikhar Ambreen, Nida |
| description | In the present study, a series of N-substituted derivatives of 2-phenylethylamine has been synthesized. The reaction of 2-phenylethylamine (1) with benzene sulfonyl chloride (2) yielded N-(2-phenylethyl) benzenesulfonamide (3), which further on treatment with alkyl/acyl halides (4a-i) in the presence of sodium hydride furnished into N-substituted sulfonamides (5a-i). These derivatives were characterized by IR, (1)H-NMR and EI-MS and then screened against acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase enzyme (LOX) and were found to be potent inhibitors of butyryl cholinesterase only. |
| format | Article |
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The reaction of 2-phenylethylamine (1) with benzene sulfonyl chloride (2) yielded N-(2-phenylethyl) benzenesulfonamide (3), which further on treatment with alkyl/acyl halides (4a-i) in the presence of sodium hydride furnished into N-substituted sulfonamides (5a-i). These derivatives were characterized by IR, (1)H-NMR and EI-MS and then screened against acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase enzyme (LOX) and were found to be potent inhibitors of butyryl cholinesterase only.</description><identifier>ISSN: 1011-601X</identifier><identifier>PMID: 23009998</identifier><language>eng</language><publisher>Pakistan: Pakistan Journal of Pharmaceutical Sciences</publisher><subject>Acetylcholinesterase - metabolism ; Butyrylcholinesterase - metabolism ; Chemical properties ; Chemical synthesis ; Cholinesterase Inhibitors - chemical synthesis ; Cholinesterase Inhibitors - pharmacology ; Composition ; Identification and classification ; Lipoxygenase Inhibitors - chemical synthesis ; Lipoxygenase Inhibitors - pharmacology ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Methods ; Molecular Structure ; Phenethylamines ; Phenethylamines - chemical synthesis ; Phenethylamines - pharmacology ; Production processes ; Spectrophotometry, Infrared ; Sulfonamides ; Sulfonamides - chemical synthesis ; Sulfonamides - pharmacology</subject><ispartof>Pakistan journal of pharmaceutical sciences, 2012-10, Vol.25 (4), p.809-814</ispartof><rights>COPYRIGHT 2012 Pakistan Journal of Pharmaceutical Sciences</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23009998$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rehman, Aziz-ur</creatorcontrib><creatorcontrib>Afroz, Sumbel</creatorcontrib><creatorcontrib>Abbasi, Muhammad Athar</creatorcontrib><creatorcontrib>Tanveer, Wajeeha</creatorcontrib><creatorcontrib>Khan, Khalid Mohammed</creatorcontrib><creatorcontrib>Ashraf, Muhammad</creatorcontrib><creatorcontrib>Ahmad, Irshad</creatorcontrib><creatorcontrib>Afzal, Iftikhar</creatorcontrib><creatorcontrib>Ambreen, Nida</creatorcontrib><title>Synthesis, characterization and biological screening of sulfonamides derived form 2-phenylethylamine</title><title>Pakistan journal of pharmaceutical sciences</title><addtitle>Pak J Pharm Sci</addtitle><description>In the present study, a series of N-substituted derivatives of 2-phenylethylamine has been synthesized. The reaction of 2-phenylethylamine (1) with benzene sulfonyl chloride (2) yielded N-(2-phenylethyl) benzenesulfonamide (3), which further on treatment with alkyl/acyl halides (4a-i) in the presence of sodium hydride furnished into N-substituted sulfonamides (5a-i). These derivatives were characterized by IR, (1)H-NMR and EI-MS and then screened against acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase enzyme (LOX) and were found to be potent inhibitors of butyryl cholinesterase only.</description><subject>Acetylcholinesterase - metabolism</subject><subject>Butyrylcholinesterase - metabolism</subject><subject>Chemical properties</subject><subject>Chemical synthesis</subject><subject>Cholinesterase Inhibitors - chemical synthesis</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Composition</subject><subject>Identification and classification</subject><subject>Lipoxygenase Inhibitors - chemical synthesis</subject><subject>Lipoxygenase Inhibitors - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Methods</subject><subject>Molecular Structure</subject><subject>Phenethylamines</subject><subject>Phenethylamines - chemical synthesis</subject><subject>Phenethylamines - pharmacology</subject><subject>Production processes</subject><subject>Spectrophotometry, Infrared</subject><subject>Sulfonamides</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - pharmacology</subject><issn>1011-601X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo10EFLwzAUB_AcFDenX0ECXjxYSJusTY5jqBMGHlTwVtLkpY2kyWxaoX56I5un9w6__x_eO0PLnOR5VpL8Y4EuY_wkpGRCiAu0KCghaeNLpF9nP3YQbbzHqpODVCMM9keONngsvcaNDS60VkmHoxoAvPUtDgbHyZngZW81RKxT5hs0NmHocZEdOvCzg7GbXQIertC5kS7C9Wmu0Pvjw9t2l-1fnp63m33WFlSMGVMGCOWMAzCimSxzUMxQwypDGK0UQGOgVJWAhpSFUWJNlNaqYoJI3jBJV-ju2HsYwtcEcax7GxU4Jz2EKdY54YRzuhZlordH2koHtfUmjOn2P15vaBIVFZwldXMqnJoedH0YbC-Huf7_H_0F6n5tMg</recordid><startdate>201210</startdate><enddate>201210</enddate><creator>Rehman, Aziz-ur</creator><creator>Afroz, Sumbel</creator><creator>Abbasi, Muhammad Athar</creator><creator>Tanveer, Wajeeha</creator><creator>Khan, Khalid Mohammed</creator><creator>Ashraf, Muhammad</creator><creator>Ahmad, Irshad</creator><creator>Afzal, Iftikhar</creator><creator>Ambreen, Nida</creator><general>Pakistan Journal of Pharmaceutical Sciences</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>201210</creationdate><title>Synthesis, characterization and biological screening of sulfonamides derived form 2-phenylethylamine</title><author>Rehman, Aziz-ur ; Afroz, Sumbel ; Abbasi, Muhammad Athar ; Tanveer, Wajeeha ; Khan, Khalid Mohammed ; Ashraf, Muhammad ; Ahmad, Irshad ; Afzal, Iftikhar ; Ambreen, Nida</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g239t-4cfe03848ee40d4a61ec4f3f47f0437ceebfe6c79eb062fc950cddc7490a8b4a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acetylcholinesterase - metabolism</topic><topic>Butyrylcholinesterase - metabolism</topic><topic>Chemical properties</topic><topic>Chemical synthesis</topic><topic>Cholinesterase Inhibitors - chemical synthesis</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Composition</topic><topic>Identification and classification</topic><topic>Lipoxygenase Inhibitors - chemical synthesis</topic><topic>Lipoxygenase Inhibitors - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Methods</topic><topic>Molecular Structure</topic><topic>Phenethylamines</topic><topic>Phenethylamines - chemical synthesis</topic><topic>Phenethylamines - pharmacology</topic><topic>Production processes</topic><topic>Spectrophotometry, Infrared</topic><topic>Sulfonamides</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonamides - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rehman, Aziz-ur</creatorcontrib><creatorcontrib>Afroz, Sumbel</creatorcontrib><creatorcontrib>Abbasi, Muhammad Athar</creatorcontrib><creatorcontrib>Tanveer, Wajeeha</creatorcontrib><creatorcontrib>Khan, Khalid Mohammed</creatorcontrib><creatorcontrib>Ashraf, Muhammad</creatorcontrib><creatorcontrib>Ahmad, Irshad</creatorcontrib><creatorcontrib>Afzal, Iftikhar</creatorcontrib><creatorcontrib>Ambreen, Nida</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Pakistan journal of pharmaceutical sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rehman, Aziz-ur</au><au>Afroz, Sumbel</au><au>Abbasi, Muhammad Athar</au><au>Tanveer, Wajeeha</au><au>Khan, Khalid Mohammed</au><au>Ashraf, Muhammad</au><au>Ahmad, Irshad</au><au>Afzal, Iftikhar</au><au>Ambreen, Nida</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization and biological screening of sulfonamides derived form 2-phenylethylamine</atitle><jtitle>Pakistan journal of pharmaceutical sciences</jtitle><addtitle>Pak J Pharm Sci</addtitle><date>2012-10</date><risdate>2012</risdate><volume>25</volume><issue>4</issue><spage>809</spage><epage>814</epage><pages>809-814</pages><issn>1011-601X</issn><abstract>In the present study, a series of N-substituted derivatives of 2-phenylethylamine has been synthesized. The reaction of 2-phenylethylamine (1) with benzene sulfonyl chloride (2) yielded N-(2-phenylethyl) benzenesulfonamide (3), which further on treatment with alkyl/acyl halides (4a-i) in the presence of sodium hydride furnished into N-substituted sulfonamides (5a-i). These derivatives were characterized by IR, (1)H-NMR and EI-MS and then screened against acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase enzyme (LOX) and were found to be potent inhibitors of butyryl cholinesterase only.</abstract><cop>Pakistan</cop><pub>Pakistan Journal of Pharmaceutical Sciences</pub><pmid>23009998</pmid><tpages>6</tpages></addata></record> |
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| ispartof | Pakistan journal of pharmaceutical sciences, 2012-10, Vol.25 (4), p.809-814 |
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| language | eng |
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| source | MEDLINE; EZB-FREE-00999 freely available EZB journals |
| subjects | Acetylcholinesterase - metabolism Butyrylcholinesterase - metabolism Chemical properties Chemical synthesis Cholinesterase Inhibitors - chemical synthesis Cholinesterase Inhibitors - pharmacology Composition Identification and classification Lipoxygenase Inhibitors - chemical synthesis Lipoxygenase Inhibitors - pharmacology Magnetic Resonance Spectroscopy Mass Spectrometry Methods Molecular Structure Phenethylamines Phenethylamines - chemical synthesis Phenethylamines - pharmacology Production processes Spectrophotometry, Infrared Sulfonamides Sulfonamides - chemical synthesis Sulfonamides - pharmacology |
| title | Synthesis, characterization and biological screening of sulfonamides derived form 2-phenylethylamine |
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