Synthesis and pharmacological investigation of novel 4 -benzyl -1 -substituted -4H-[1,2,4 ]triazolo [4,3 -a]quinazolin -5 -ones as new class of H1-antihistaminic agents
A series of novel 1-substituted-4-benzyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones were synthesized by the cyclization of 2-hydrazino-3-benzyl-3H-quinazolin-4-one with various one-carbon donors. The starting material 2-hydrazino-3-benzyl-3H-quinazolin-4-one was synthesized from benzylamine by a new...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-06, Vol.15 (12), p.4009-4015 |
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| creator | ALAGARSAMY, V SOLOMON, V. R MURUGAN, M |
| description | A series of novel 1-substituted-4-benzyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones were synthesized by the cyclization of 2-hydrazino-3-benzyl-3H-quinazolin-4-one with various one-carbon donors. The starting material 2-hydrazino-3-benzyl-3H-quinazolin-4-one was synthesized from benzylamine by a new innovative route. When tested for their in vivo H1 -antihistaminic activity on guinea pigs, all the test compounds protected the animals from histamine induced bronchospasm significantly. The compound 1-methyl-4-benzyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one (II) emerged as the most active compound of the series and it is more potent (percent protection 76%) when compared to the reference standard chlorpheniramine maleate (percent protection 71%). Compound II showed negligible sedation (7%) when compared to chlorpheniramine maleate (30%). Hence it could serve as prototype molecule for further development as a new class of H1 -antihistamines. |
| doi_str_mv | 10.1016/j.bmc.2007.04.001 |
| format | Article |
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Hence it could serve as prototype molecule for further development as a new class of H1 -antihistamines.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.04.001</identifier><identifier>PMID: 17452107</identifier><language>eng</language><publisher>Oxford: Elsevier Science</publisher><subject>Animals ; Biological and medical sciences ; Guinea Pigs ; Histamine and antagonists. Allergy ; Histamine H1 Antagonists - chemical synthesis ; Histamine H1 Antagonists - chemistry ; Histamine H1 Antagonists - pharmacology ; Magnetic Resonance Spectroscopy ; Male ; Medical sciences ; Mice ; Pharmacology. Drug treatments ; Quinazolines - chemical synthesis ; Quinazolines - chemistry ; Quinazolines - pharmacology ; Spectrophotometry, Infrared</subject><ispartof>Bioorganic & medicinal chemistry, 2007-06, Vol.15 (12), p.4009-4015</ispartof><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c244t-7b9b922faef6299367e15051a07665dc01dcec2c1a1dada21ee3512cbd45bf3c3</citedby><cites>FETCH-LOGICAL-c244t-7b9b922faef6299367e15051a07665dc01dcec2c1a1dada21ee3512cbd45bf3c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18744910$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17452107$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>ALAGARSAMY, V</creatorcontrib><creatorcontrib>SOLOMON, V. R</creatorcontrib><creatorcontrib>MURUGAN, M</creatorcontrib><title>Synthesis and pharmacological investigation of novel 4 -benzyl -1 -substituted -4H-[1,2,4 ]triazolo [4,3 -a]quinazolin -5 -ones as new class of H1-antihistaminic agents</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of novel 1-substituted-4-benzyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones were synthesized by the cyclization of 2-hydrazino-3-benzyl-3H-quinazolin-4-one with various one-carbon donors. The starting material 2-hydrazino-3-benzyl-3H-quinazolin-4-one was synthesized from benzylamine by a new innovative route. When tested for their in vivo H1 -antihistaminic activity on guinea pigs, all the test compounds protected the animals from histamine induced bronchospasm significantly. The compound 1-methyl-4-benzyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one (II) emerged as the most active compound of the series and it is more potent (percent protection 76%) when compared to the reference standard chlorpheniramine maleate (percent protection 71%). Compound II showed negligible sedation (7%) when compared to chlorpheniramine maleate (30%). Hence it could serve as prototype molecule for further development as a new class of H1 -antihistamines.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Guinea Pigs</subject><subject>Histamine and antagonists. Allergy</subject><subject>Histamine H1 Antagonists - chemical synthesis</subject><subject>Histamine H1 Antagonists - chemistry</subject><subject>Histamine H1 Antagonists - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - chemistry</subject><subject>Quinazolines - pharmacology</subject><subject>Spectrophotometry, Infrared</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkcFq3DAQhkVpabZpH6CXokt7WjkzsmyvjyW02UKgh6SnEMRYlne12PLGklM2T5THjJYs5DQwfPMPMx9jXxEyBCwvdlkzmEwCVBmoDADfsQWqUok8r_E9W0BdrgSs6vKMfQphBwBS1fiRnWGlColQLdjzzcHHrQ0ucPIt329pGsiM_bhxhnru_KMN0W0outHzseN-fLQ9V1w01j8dei6QizA3iYlztC0Xai3ucCmXit_HydFTiuJ3aplzQfcPs_PHjvNcFFyM3qatgXv7n5ueQjguWKMgH93WhUiD885w2lgfw2f2oaM-2C-nes7-_f51e7kW13-v_lz-vBZGKhVF1dRNLWVHtitlXedlZbGAAgmqsixaA9gaa6RBwpZakmhtXqA0TauKpstNfs5-vObup_FhTsfrwQVj-568HeegK1BVkWORQHwFzTSGMNlO7yc30HTQCPqoR-900qOPejQonfSkmW-n8LkZbPs2cfKRgO8ngEL6fzeRNy68catKJYOQvwDxuJl-</recordid><startdate>20070615</startdate><enddate>20070615</enddate><creator>ALAGARSAMY, V</creator><creator>SOLOMON, V. 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Allergy</topic><topic>Histamine H1 Antagonists - chemical synthesis</topic><topic>Histamine H1 Antagonists - chemistry</topic><topic>Histamine H1 Antagonists - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>Quinazolines - pharmacology</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ALAGARSAMY, V</creatorcontrib><creatorcontrib>SOLOMON, V. R</creatorcontrib><creatorcontrib>MURUGAN, M</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><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>ALAGARSAMY, V</au><au>SOLOMON, V. R</au><au>MURUGAN, M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and pharmacological investigation of novel 4 -benzyl -1 -substituted -4H-[1,2,4 ]triazolo [4,3 -a]quinazolin -5 -ones as new class of H1-antihistaminic agents</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2007-06-15</date><risdate>2007</risdate><volume>15</volume><issue>12</issue><spage>4009</spage><epage>4015</epage><pages>4009-4015</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of novel 1-substituted-4-benzyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones were synthesized by the cyclization of 2-hydrazino-3-benzyl-3H-quinazolin-4-one with various one-carbon donors. The starting material 2-hydrazino-3-benzyl-3H-quinazolin-4-one was synthesized from benzylamine by a new innovative route. When tested for their in vivo H1 -antihistaminic activity on guinea pigs, all the test compounds protected the animals from histamine induced bronchospasm significantly. The compound 1-methyl-4-benzyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one (II) emerged as the most active compound of the series and it is more potent (percent protection 76%) when compared to the reference standard chlorpheniramine maleate (percent protection 71%). Compound II showed negligible sedation (7%) when compared to chlorpheniramine maleate (30%). Hence it could serve as prototype molecule for further development as a new class of H1 -antihistamines.</abstract><cop>Oxford</cop><pub>Elsevier Science</pub><pmid>17452107</pmid><doi>10.1016/j.bmc.2007.04.001</doi><tpages>7</tpages></addata></record> |
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| subjects | Animals Biological and medical sciences Guinea Pigs Histamine and antagonists. Allergy Histamine H1 Antagonists - chemical synthesis Histamine H1 Antagonists - chemistry Histamine H1 Antagonists - pharmacology Magnetic Resonance Spectroscopy Male Medical sciences Mice Pharmacology. Drug treatments Quinazolines - chemical synthesis Quinazolines - chemistry Quinazolines - pharmacology Spectrophotometry, Infrared |
| title | Synthesis and pharmacological investigation of novel 4 -benzyl -1 -substituted -4H-[1,2,4 ]triazolo [4,3 -a]quinazolin -5 -ones as new class of H1-antihistaminic agents |
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