Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates
A novel series of diphenyl 1-(arylamino)-1-(pyridin-3-yl)ethylphosphonates 1–5 was obtained in high yields from reactions of 3-acetyl pyridine with aromatic amines and triphenylphosphite in the presence of lithium perchlorate as a catalyst. The structures of the synthesized compounds were confirmed...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2012-04, Vol.20 (7), p.2252-2258 |
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| creator | Abdel-Megeed, Mohamed F. Badr, Badr E. Azaam, Mohamed M. El-Hiti, Gamal A. |
| description | A novel series of diphenyl 1-(arylamino)-1-(pyridin-3-yl)ethylphosphonates 1–5 was obtained in high yields from reactions of 3-acetyl pyridine with aromatic amines and triphenylphosphite in the presence of lithium perchlorate as a catalyst. The structures of the synthesized compounds were confirmed by IR, 1H NMR spectral data and microanalyses. Compounds 1–5 showed high antimicrobial activities against Escherichia coli (NCIM2065) as a Gram-negative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candidaalbicans and Saccharomyces cerevisiae as fungi, at low concentrations (10–100μg/mL). Also, the synthesized compounds showed significant cytotoxicity anticancer activities against liver carcinoma cell line (HepG2) and human breast adenocarcinoma cell line (MCF7). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use. |
| doi_str_mv | 10.1016/j.bmc.2012.02.015 |
| format | Article |
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The structures of the synthesized compounds were confirmed by IR, 1H NMR spectral data and microanalyses. Compounds 1–5 showed high antimicrobial activities against Escherichia coli (NCIM2065) as a Gram-negative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candidaalbicans and Saccharomyces cerevisiae as fungi, at low concentrations (10–100μg/mL). Also, the synthesized compounds showed significant cytotoxicity anticancer activities against liver carcinoma cell line (HepG2) and human breast adenocarcinoma cell line (MCF7). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2012.02.015</identifier><identifier>PMID: 22370339</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Adenocarcinoma ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - pharmacology ; anti-infective properties ; Anticancer ; anticarcinogenic activity ; Antimicrobial ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; aromatic amines ; Bacillus subtilis ; Biological and medical sciences ; biphenyl ; catalysts ; Cell Line, Tumor ; Cell Proliferation - drug effects ; chemistry ; cytotoxicity ; Diphenyl 1-(pyridin-3-yl)ethylphosphonates ; Escherichia coli ; fungi ; Fungi - drug effects ; Gram-negative bacteria ; Gram-Negative Bacteria - drug effects ; Gram-positive bacteria ; Gram-Positive Bacteria - drug effects ; Hep G2 Cells ; Humans ; Lethal dose ; lithium ; liver ; Medical sciences ; Microbial Sensitivity Tests ; nuclear magnetic resonance spectroscopy ; Organophosphonates - chemistry ; Organophosphonates - pharmacology ; Pharmacology. Drug treatments ; Phosphorous Acids - chemistry ; Phosphorous Acids - pharmacology ; pyridines ; Pyridines - chemistry ; Saccharomyces cerevisiae ; spectral analysis ; Staphylococcus aureus ; α-Aminophosphonate</subject><ispartof>Bioorganic & medicinal chemistry, 2012-04, Vol.20 (7), p.2252-2258</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-37f83cd57f3eac718b1cf1430d9f575a690f5b30b17acf24f08e5722350f461d3</citedby><cites>FETCH-LOGICAL-c438t-37f83cd57f3eac718b1cf1430d9f575a690f5b30b17acf24f08e5722350f461d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089612001083$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25721376$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22370339$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abdel-Megeed, Mohamed F.</creatorcontrib><creatorcontrib>Badr, Badr E.</creatorcontrib><creatorcontrib>Azaam, Mohamed M.</creatorcontrib><creatorcontrib>El-Hiti, Gamal A.</creatorcontrib><title>Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A novel series of diphenyl 1-(arylamino)-1-(pyridin-3-yl)ethylphosphonates 1–5 was obtained in high yields from reactions of 3-acetyl pyridine with aromatic amines and triphenylphosphite in the presence of lithium perchlorate as a catalyst. The structures of the synthesized compounds were confirmed by IR, 1H NMR spectral data and microanalyses. Compounds 1–5 showed high antimicrobial activities against Escherichia coli (NCIM2065) as a Gram-negative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candidaalbicans and Saccharomyces cerevisiae as fungi, at low concentrations (10–100μg/mL). Also, the synthesized compounds showed significant cytotoxicity anticancer activities against liver carcinoma cell line (HepG2) and human breast adenocarcinoma cell line (MCF7). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use.</description><subject>Adenocarcinoma</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>anti-infective properties</subject><subject>Anticancer</subject><subject>anticarcinogenic activity</subject><subject>Antimicrobial</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>aromatic amines</subject><subject>Bacillus subtilis</subject><subject>Biological and medical sciences</subject><subject>biphenyl</subject><subject>catalysts</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>chemistry</subject><subject>cytotoxicity</subject><subject>Diphenyl 1-(pyridin-3-yl)ethylphosphonates</subject><subject>Escherichia coli</subject><subject>fungi</subject><subject>Fungi - drug effects</subject><subject>Gram-negative bacteria</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-positive bacteria</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Lethal dose</subject><subject>lithium</subject><subject>liver</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Organophosphonates - chemistry</subject><subject>Organophosphonates - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Phosphorous Acids - chemistry</subject><subject>Phosphorous Acids - pharmacology</subject><subject>pyridines</subject><subject>Pyridines - chemistry</subject><subject>Saccharomyces cerevisiae</subject><subject>spectral analysis</subject><subject>Staphylococcus aureus</subject><subject>α-Aminophosphonate</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU2P1DAMhiMEYmcXfgAX6AUBEh3spmlacUIrvqSVOCx7jtLUYTLqx5B0Ruq_x7MzwA0kR1Gsx3b8vkI8Q1gjYPVuu24Hty4AizVwoHogVlhWZS5lgw_FCpqqzqFuqgtxmdIWAIqywcfioiikBoZWIt4u47yhFNLbzI5zGIKLUxtsz6_uPuPs6Chm1s3hEOZAKZt8ZrNxOlCfJYrnTBd2GxqXPsP89W6JoQtjLvOlf0PzZul3mynxGe1M6Yl45G2f6On5vhJ3nz5-v_6S33z7_PX6w03uSlnPudS-lq5T2kuyTmPdovNYSugar7SyVQNetRJa1Nb5ovRQk9K8mQJfVtjJK_Hq1HcXp597SrMZQnLU93akaZ8Mi4O6kUr-nyxqqbGqjySeSFYppUje7GIYbFwMgjl6YraGPTFHTwxwoOKa5-fu-3ag7k_FbxMYeHkGbHK295EVD-kvx1uh1BVzL06ct5OxPyIzd7c8SQEgQgEFE-9PBLGuh0DRJBeI_etCJDebbgr_-Ogv2Muy6A</recordid><startdate>20120401</startdate><enddate>20120401</enddate><creator>Abdel-Megeed, Mohamed F.</creator><creator>Badr, Badr E.</creator><creator>Azaam, Mohamed M.</creator><creator>El-Hiti, Gamal A.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20120401</creationdate><title>Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates</title><author>Abdel-Megeed, Mohamed F. ; Badr, Badr E. ; Azaam, Mohamed M. ; El-Hiti, Gamal A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-37f83cd57f3eac718b1cf1430d9f575a690f5b30b17acf24f08e5722350f461d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Adenocarcinoma</topic><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>anti-infective properties</topic><topic>Anticancer</topic><topic>anticarcinogenic activity</topic><topic>Antimicrobial</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>aromatic amines</topic><topic>Bacillus subtilis</topic><topic>Biological and medical sciences</topic><topic>biphenyl</topic><topic>catalysts</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>chemistry</topic><topic>cytotoxicity</topic><topic>Diphenyl 1-(pyridin-3-yl)ethylphosphonates</topic><topic>Escherichia coli</topic><topic>fungi</topic><topic>Fungi - drug effects</topic><topic>Gram-negative bacteria</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-positive bacteria</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Hep G2 Cells</topic><topic>Humans</topic><topic>Lethal dose</topic><topic>lithium</topic><topic>liver</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Organophosphonates - chemistry</topic><topic>Organophosphonates - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Phosphorous Acids - chemistry</topic><topic>Phosphorous Acids - pharmacology</topic><topic>pyridines</topic><topic>Pyridines - chemistry</topic><topic>Saccharomyces cerevisiae</topic><topic>spectral analysis</topic><topic>Staphylococcus aureus</topic><topic>α-Aminophosphonate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abdel-Megeed, Mohamed F.</creatorcontrib><creatorcontrib>Badr, Badr E.</creatorcontrib><creatorcontrib>Azaam, Mohamed M.</creatorcontrib><creatorcontrib>El-Hiti, Gamal A.</creatorcontrib><collection>AGRIS</collection><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>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abdel-Megeed, Mohamed F.</au><au>Badr, Badr E.</au><au>Azaam, Mohamed M.</au><au>El-Hiti, Gamal A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2012-04-01</date><risdate>2012</risdate><volume>20</volume><issue>7</issue><spage>2252</spage><epage>2258</epage><pages>2252-2258</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A novel series of diphenyl 1-(arylamino)-1-(pyridin-3-yl)ethylphosphonates 1–5 was obtained in high yields from reactions of 3-acetyl pyridine with aromatic amines and triphenylphosphite in the presence of lithium perchlorate as a catalyst. The structures of the synthesized compounds were confirmed by IR, 1H NMR spectral data and microanalyses. Compounds 1–5 showed high antimicrobial activities against Escherichia coli (NCIM2065) as a Gram-negative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candidaalbicans and Saccharomyces cerevisiae as fungi, at low concentrations (10–100μg/mL). Also, the synthesized compounds showed significant cytotoxicity anticancer activities against liver carcinoma cell line (HepG2) and human breast adenocarcinoma cell line (MCF7). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22370339</pmid><doi>10.1016/j.bmc.2012.02.015</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2012-04, Vol.20 (7), p.2252-2258 |
| issn | 0968-0896 1464-3391 |
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| subjects | Adenocarcinoma Anti-Infective Agents - chemical synthesis Anti-Infective Agents - pharmacology anti-infective properties Anticancer anticarcinogenic activity Antimicrobial Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology aromatic amines Bacillus subtilis Biological and medical sciences biphenyl catalysts Cell Line, Tumor Cell Proliferation - drug effects chemistry cytotoxicity Diphenyl 1-(pyridin-3-yl)ethylphosphonates Escherichia coli fungi Fungi - drug effects Gram-negative bacteria Gram-Negative Bacteria - drug effects Gram-positive bacteria Gram-Positive Bacteria - drug effects Hep G2 Cells Humans Lethal dose lithium liver Medical sciences Microbial Sensitivity Tests nuclear magnetic resonance spectroscopy Organophosphonates - chemistry Organophosphonates - pharmacology Pharmacology. Drug treatments Phosphorous Acids - chemistry Phosphorous Acids - pharmacology pyridines Pyridines - chemistry Saccharomyces cerevisiae spectral analysis Staphylococcus aureus α-Aminophosphonate |
| title | Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates |
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