Novel Pyrimidinone Derivatives: Synthesis, Antitumor and Antimicrobial Evaluation
Starting from 6-aryl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4a-d), a series of mono- and dialkyl derivatives 5a-j and 6a, b was synthesized. Hydrazinolysis of 4a, b, d and 5d afforded the hydrazino derivatives 7a-c which were cyclised to give the triazolopyrimidinones 8a-c and t...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2012/04/01, Vol.60(4), pp.521-530 |
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| creator | Taher, Azza Taher Helwa, Amira Atef |
| description | Starting from 6-aryl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4a-d), a series of mono- and dialkyl derivatives 5a-j and 6a, b was synthesized. Hydrazinolysis of 4a, b, d and 5d afforded the hydrazino derivatives 7a-c which were cyclised to give the triazolopyrimidinones 8a-c and the pyrimidotriazinones 9a-c through the reaction with formic acid and chloroacetyl chloride, respectively. Most of the newly synthesized compounds were evaluated for their in-vitro antitumor activity. Compounds 6a and b displayed promising anticancer activity against leukaemia, non-small cell lung, melanoma, and renal cancer. On the other hand, all compounds prepared were screened for their in-vitro antibacterial and antifungal activities. Compounds 5h and j showed significant activity against Staphylococcus aureus, while compounds 5e, 7c and 8c displayed moderate inhibitory activity against Candida albicans. |
| doi_str_mv | 10.1248/cpb.60.521 |
| format | Article |
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Hydrazinolysis of 4a, b, d and 5d afforded the hydrazino derivatives 7a-c which were cyclised to give the triazolopyrimidinones 8a-c and the pyrimidotriazinones 9a-c through the reaction with formic acid and chloroacetyl chloride, respectively. Most of the newly synthesized compounds were evaluated for their in-vitro antitumor activity. Compounds 6a and b displayed promising anticancer activity against leukaemia, non-small cell lung, melanoma, and renal cancer. On the other hand, all compounds prepared were screened for their in-vitro antibacterial and antifungal activities. Compounds 5h and j showed significant activity against Staphylococcus aureus, while compounds 5e, 7c and 8c displayed moderate inhibitory activity against Candida albicans.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.60.521</identifier><identifier>PMID: 22466736</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; antimicrobial activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; antitumor activity ; Candida albicans - drug effects ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Drug Screening Assays, Antitumor ; Humans ; Microbial Sensitivity Tests ; pyrimidinone ; Pyrimidinones - chemical synthesis ; Pyrimidinones - chemistry ; Pyrimidinones - pharmacology ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship ; synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2012/04/01, Vol.60(4), pp.521-530</ispartof><rights>2012 The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c525t-d010efb2e5959b85daa10cf561609ac5d466db486adb8dcdd756555f6350e1c43</citedby><cites>FETCH-LOGICAL-c525t-d010efb2e5959b85daa10cf561609ac5d466db486adb8dcdd756555f6350e1c43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22466736$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Taher, Azza Taher</creatorcontrib><creatorcontrib>Helwa, Amira Atef</creatorcontrib><title>Novel Pyrimidinone Derivatives: Synthesis, Antitumor and Antimicrobial Evaluation</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Starting from 6-aryl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4a-d), a series of mono- and dialkyl derivatives 5a-j and 6a, b was synthesized. Hydrazinolysis of 4a, b, d and 5d afforded the hydrazino derivatives 7a-c which were cyclised to give the triazolopyrimidinones 8a-c and the pyrimidotriazinones 9a-c through the reaction with formic acid and chloroacetyl chloride, respectively. Most of the newly synthesized compounds were evaluated for their in-vitro antitumor activity. Compounds 6a and b displayed promising anticancer activity against leukaemia, non-small cell lung, melanoma, and renal cancer. On the other hand, all compounds prepared were screened for their in-vitro antibacterial and antifungal activities. Compounds 5h and j showed significant activity against Staphylococcus aureus, while compounds 5e, 7c and 8c displayed moderate inhibitory activity against Candida albicans.</description><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antimicrobial activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>antitumor activity</subject><subject>Candida albicans - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Microbial Sensitivity Tests</subject><subject>pyrimidinone</subject><subject>Pyrimidinones - chemical synthesis</subject><subject>Pyrimidinones - chemistry</subject><subject>Pyrimidinones - pharmacology</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkElPwzAQhS0EomW58ANQbkiIFC-xk3BBVVklxCLgbDn2hLrKUuwkUv89hlK4zGg03zy9eQgdETwhNMnO9bKYCDzhlGyhMWFJGnNK2TYaY4zzmDLBRmjP-wXGlOOU7aIRpYkQKRNj9PLYDlBFzytna2ts0zYQXYGzg-rsAP4iel013Ry89WfRtOls19eti1RjfqbaatcWVlXR9aCqPty0zQHaKVXl4fC376P3m-u32V388HR7P5s-xJpT3sUGEwxlQYHnPC8ybpQiWJdcEIFzpbkJDk2RZEKZIjPamJQLznkpGMdAdML20clad-nazx58J2vrNVSVaqDtvcwFy2guUh7I0zUZzHrvoJTL8K1yK0mw_E5QhgSlwDIkGODjX9m-qMH8oZvIAnC5Bha-Ux_wByjXWV3BRitZlyD5v5krJ6FhX6H9g-k</recordid><startdate>2012</startdate><enddate>2012</enddate><creator>Taher, Azza Taher</creator><creator>Helwa, Amira Atef</creator><general>The Pharmaceutical Society of Japan</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>2012</creationdate><title>Novel Pyrimidinone Derivatives: Synthesis, Antitumor and Antimicrobial Evaluation</title><author>Taher, Azza Taher ; Helwa, Amira Atef</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c525t-d010efb2e5959b85daa10cf561609ac5d466db486adb8dcdd756555f6350e1c43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antimicrobial activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>antitumor activity</topic><topic>Candida albicans - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Microbial Sensitivity Tests</topic><topic>pyrimidinone</topic><topic>Pyrimidinones - chemical synthesis</topic><topic>Pyrimidinones - chemistry</topic><topic>Pyrimidinones - pharmacology</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Taher, Azza Taher</creatorcontrib><creatorcontrib>Helwa, Amira Atef</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>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taher, Azza Taher</au><au>Helwa, Amira Atef</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Pyrimidinone Derivatives: Synthesis, Antitumor and Antimicrobial Evaluation</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2012</date><risdate>2012</risdate><volume>60</volume><issue>4</issue><spage>521</spage><epage>530</epage><pages>521-530</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Starting from 6-aryl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4a-d), a series of mono- and dialkyl derivatives 5a-j and 6a, b was synthesized. Hydrazinolysis of 4a, b, d and 5d afforded the hydrazino derivatives 7a-c which were cyclised to give the triazolopyrimidinones 8a-c and the pyrimidotriazinones 9a-c through the reaction with formic acid and chloroacetyl chloride, respectively. Most of the newly synthesized compounds were evaluated for their in-vitro antitumor activity. Compounds 6a and b displayed promising anticancer activity against leukaemia, non-small cell lung, melanoma, and renal cancer. On the other hand, all compounds prepared were screened for their in-vitro antibacterial and antifungal activities. Compounds 5h and j showed significant activity against Staphylococcus aureus, while compounds 5e, 7c and 8c displayed moderate inhibitory activity against Candida albicans.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>22466736</pmid><doi>10.1248/cpb.60.521</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology antimicrobial activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology antitumor activity Candida albicans - drug effects Cell Line, Tumor Cell Proliferation - drug effects Drug Screening Assays, Antitumor Humans Microbial Sensitivity Tests pyrimidinone Pyrimidinones - chemical synthesis Pyrimidinones - chemistry Pyrimidinones - pharmacology Staphylococcus aureus - drug effects Structure-Activity Relationship synthesis |
| title | Novel Pyrimidinone Derivatives: Synthesis, Antitumor and Antimicrobial Evaluation |
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