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Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies
Pyrazoline derivatives with unsubstituted ring A and substituted ring C ( 5– 16) were found to be potent inhibitors of MAO-A isoform with SI MAO-A in the order of 10 3 and 10 4. Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molec...
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| Published in: | Bioorganic & medicinal chemistry letters 2011-07, Vol.21 (14), p.4296-4300 |
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| Main Authors: | , , , , , , , , |
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| cites | cdi_FETCH-LOGICAL-c417t-7f914ac753a9fe9e78a52ade2b1c37b92554a55810d92deae15799e32b8d3bed3 |
| container_end_page | 4300 |
| container_issue | 14 |
| container_start_page | 4296 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 21 |
| creator | Jagrat, Monika Behera, Jagannath Yabanoglu, Samiye Ercan, Ayse Ucar, Gulberk Sinha, Barij Nayan Sankaran, Vadivelan Basu, Arijit Jayaprakash, Venkatesan |
| description | Pyrazoline derivatives with unsubstituted ring A and substituted ring C (
5–
16) were found to be potent inhibitors of MAO-A isoform with SI
MAO-A in the order of 10
3 and 10
4.
Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molecules with unsubstituted ring A and substituted ring C (
5–
16) were found to be potent inhibitors of hMAO-A isoform with SI
MAO-A in the order 10
3 and 10
4. Ten molecules with unsubstituted ring A and without ring C (
21–
30), in which eight molecules (
21,
23–
26, and
28–
30) were selective for hMAO-A, one for hMAO-B (
22) and the other one non-selective (
27). Presence of ring C increases potency as well as SI towards hMAO-A; however its absence decreases both potency and SI towards hMAO-A and hMAO-B. |
| doi_str_mv | 10.1016/j.bmcl.2011.05.057 |
| format | article |
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5–
16) were found to be potent inhibitors of MAO-A isoform with SI
MAO-A in the order of 10
3 and 10
4.
Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molecules with unsubstituted ring A and substituted ring C (
5–
16) were found to be potent inhibitors of hMAO-A isoform with SI
MAO-A in the order 10
3 and 10
4. Ten molecules with unsubstituted ring A and without ring C (
21–
30), in which eight molecules (
21,
23–
26, and
28–
30) were selective for hMAO-A, one for hMAO-B (
22) and the other one non-selective (
27). Presence of ring C increases potency as well as SI towards hMAO-A; however its absence decreases both potency and SI towards hMAO-A and hMAO-B.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.05.057</identifier><identifier>PMID: 21680183</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anticonvulsants. Antiepileptics. Antiparkinson agents ; Binding Sites ; Biological and medical sciences ; Computer Simulation ; Docking ; Humans ; MAO ; Medical sciences ; Monoamine Oxidase - chemistry ; Monoamine Oxidase - metabolism ; Monoamine Oxidase Inhibitors - chemical synthesis ; Monoamine Oxidase Inhibitors - chemistry ; Monoamine Oxidase Inhibitors - pharmacology ; Neuropharmacology ; Pharmacology. Drug treatments ; Protein Isoforms - antagonists & inhibitors ; Protein Isoforms - metabolism ; Protein Structure, Tertiary ; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer ; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) ; Psychology. Psychoanalysis. Psychiatry ; Psychopharmacology ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Pyrazolines ; Selectivity ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-07, Vol.21 (14), p.4296-4300</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c417t-7f914ac753a9fe9e78a52ade2b1c37b92554a55810d92deae15799e32b8d3bed3</citedby><cites>FETCH-LOGICAL-c417t-7f914ac753a9fe9e78a52ade2b1c37b92554a55810d92deae15799e32b8d3bed3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24343636$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21680183$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jagrat, Monika</creatorcontrib><creatorcontrib>Behera, Jagannath</creatorcontrib><creatorcontrib>Yabanoglu, Samiye</creatorcontrib><creatorcontrib>Ercan, Ayse</creatorcontrib><creatorcontrib>Ucar, Gulberk</creatorcontrib><creatorcontrib>Sinha, Barij Nayan</creatorcontrib><creatorcontrib>Sankaran, Vadivelan</creatorcontrib><creatorcontrib>Basu, Arijit</creatorcontrib><creatorcontrib>Jayaprakash, Venkatesan</creatorcontrib><title>Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Pyrazoline derivatives with unsubstituted ring A and substituted ring C (
5–
16) were found to be potent inhibitors of MAO-A isoform with SI
MAO-A in the order of 10
3 and 10
4.
Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molecules with unsubstituted ring A and substituted ring C (
5–
16) were found to be potent inhibitors of hMAO-A isoform with SI
MAO-A in the order 10
3 and 10
4. Ten molecules with unsubstituted ring A and without ring C (
21–
30), in which eight molecules (
21,
23–
26, and
28–
30) were selective for hMAO-A, one for hMAO-B (
22) and the other one non-selective (
27). Presence of ring C increases potency as well as SI towards hMAO-A; however its absence decreases both potency and SI towards hMAO-A and hMAO-B.</description><subject>Anticonvulsants. Antiepileptics. Antiparkinson agents</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Computer Simulation</subject><subject>Docking</subject><subject>Humans</subject><subject>MAO</subject><subject>Medical sciences</subject><subject>Monoamine Oxidase - chemistry</subject><subject>Monoamine Oxidase - metabolism</subject><subject>Monoamine Oxidase Inhibitors - chemical synthesis</subject><subject>Monoamine Oxidase Inhibitors - chemistry</subject><subject>Monoamine Oxidase Inhibitors - pharmacology</subject><subject>Neuropharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Isoforms - antagonists & inhibitors</subject><subject>Protein Isoforms - metabolism</subject><subject>Protein Structure, Tertiary</subject><subject>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer</subject><subject>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease)</subject><subject>Psychology. Psychoanalysis. Psychiatry</subject><subject>Psychopharmacology</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Pyrazolines</subject><subject>Selectivity</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkEuLFDEURoM4OG3rH3Ah2Ygbq82zkoibZvAFM4w6Cu5CHrecNNWVMaka6Pn1VtOts1PuB3dzvsvlIPSMkhUltH29Wflt6FeMULoico56gBZUtKLhgsiHaEFMSxptxI9T9LjWDSFUECEeoVNGW02o5gv05fOuuLvcpwGwdxUivlhf4jRcJ5_GXOobfLUbxmuoqb7CPuU-_0zB9RhuXT-5MeUBuyHiq_VXXMcpJqhP0Enn-gpPj3uJvr9_9-3sY3N--eHT2fq8CYKqsVGdocIFJbkzHRhQ2knmIjBPA1feMCmFk1JTEg2L4IBKZQxw5nXkHiJfopeHuzcl_5qgjnabaoC-dwPkqVqtOWFaK_Z_UgmhqeRqJtmBDCXXWqCzNyVtXdlZSuzeud3YvXO7d26JnLMvPT-en_wW4t_KH8kz8OIIuDq764obQqr3nOCCt_Ms0dsDB7O22wTF1pBgCBBTgTDamNO__vgNwyqfMQ</recordid><startdate>20110715</startdate><enddate>20110715</enddate><creator>Jagrat, Monika</creator><creator>Behera, Jagannath</creator><creator>Yabanoglu, Samiye</creator><creator>Ercan, Ayse</creator><creator>Ucar, Gulberk</creator><creator>Sinha, Barij Nayan</creator><creator>Sankaran, Vadivelan</creator><creator>Basu, Arijit</creator><creator>Jayaprakash, Venkatesan</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</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>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20110715</creationdate><title>Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies</title><author>Jagrat, Monika ; Behera, Jagannath ; Yabanoglu, Samiye ; Ercan, Ayse ; Ucar, Gulberk ; Sinha, Barij Nayan ; Sankaran, Vadivelan ; Basu, Arijit ; Jayaprakash, Venkatesan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-7f914ac753a9fe9e78a52ade2b1c37b92554a55810d92deae15799e32b8d3bed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Anticonvulsants. Antiepileptics. Antiparkinson agents</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Computer Simulation</topic><topic>Docking</topic><topic>Humans</topic><topic>MAO</topic><topic>Medical sciences</topic><topic>Monoamine Oxidase - chemistry</topic><topic>Monoamine Oxidase - metabolism</topic><topic>Monoamine Oxidase Inhibitors - chemical synthesis</topic><topic>Monoamine Oxidase Inhibitors - chemistry</topic><topic>Monoamine Oxidase Inhibitors - pharmacology</topic><topic>Neuropharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Isoforms - antagonists & inhibitors</topic><topic>Protein Isoforms - metabolism</topic><topic>Protein Structure, Tertiary</topic><topic>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer</topic><topic>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease)</topic><topic>Psychology. Psychoanalysis. Psychiatry</topic><topic>Psychopharmacology</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Pyrazolines</topic><topic>Selectivity</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jagrat, Monika</creatorcontrib><creatorcontrib>Behera, Jagannath</creatorcontrib><creatorcontrib>Yabanoglu, Samiye</creatorcontrib><creatorcontrib>Ercan, Ayse</creatorcontrib><creatorcontrib>Ucar, Gulberk</creatorcontrib><creatorcontrib>Sinha, Barij Nayan</creatorcontrib><creatorcontrib>Sankaran, Vadivelan</creatorcontrib><creatorcontrib>Basu, Arijit</creatorcontrib><creatorcontrib>Jayaprakash, Venkatesan</creatorcontrib><collection>Pascal-Francis</collection><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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jagrat, Monika</au><au>Behera, Jagannath</au><au>Yabanoglu, Samiye</au><au>Ercan, Ayse</au><au>Ucar, Gulberk</au><au>Sinha, Barij Nayan</au><au>Sankaran, Vadivelan</au><au>Basu, Arijit</au><au>Jayaprakash, Venkatesan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-07-15</date><risdate>2011</risdate><volume>21</volume><issue>14</issue><spage>4296</spage><epage>4300</epage><pages>4296-4300</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Pyrazoline derivatives with unsubstituted ring A and substituted ring C (
5–
16) were found to be potent inhibitors of MAO-A isoform with SI
MAO-A in the order of 10
3 and 10
4.
Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molecules with unsubstituted ring A and substituted ring C (
5–
16) were found to be potent inhibitors of hMAO-A isoform with SI
MAO-A in the order 10
3 and 10
4. Ten molecules with unsubstituted ring A and without ring C (
21–
30), in which eight molecules (
21,
23–
26, and
28–
30) were selective for hMAO-A, one for hMAO-B (
22) and the other one non-selective (
27). Presence of ring C increases potency as well as SI towards hMAO-A; however its absence decreases both potency and SI towards hMAO-A and hMAO-B.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21680183</pmid><doi>10.1016/j.bmcl.2011.05.057</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2011-07, Vol.21 (14), p.4296-4300 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_883028872 |
| source | ScienceDirect Journals |
| subjects | Anticonvulsants. Antiepileptics. Antiparkinson agents Binding Sites Biological and medical sciences Computer Simulation Docking Humans MAO Medical sciences Monoamine Oxidase - chemistry Monoamine Oxidase - metabolism Monoamine Oxidase Inhibitors - chemical synthesis Monoamine Oxidase Inhibitors - chemistry Monoamine Oxidase Inhibitors - pharmacology Neuropharmacology Pharmacology. Drug treatments Protein Isoforms - antagonists & inhibitors Protein Isoforms - metabolism Protein Structure, Tertiary Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) Psychology. Psychoanalysis. Psychiatry Psychopharmacology Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Pyrazolines Selectivity Structure-Activity Relationship |
| title | Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies |
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