3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents
This work reports the synthesis and the antiviral activities of 3-benzamido, 3-phenylureido and 3-phenyl-thioureido derivatives in the imidazo[1,2-a]pyridine series. The structure was proven by NMR spectroscopy. The synthesized compounds were evaluated against a large number of viruses. The 3-phenyl...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2001, Vol.49(12), pp.1631-1635 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | CHAOUNI-BENABDALLAH, Aziz GALTIER, Christophe ALLOUCHI, Hassan KHERBECHE, Abdelak CHAVIGNON, Olivier TEULADE, Jean-Claude WITVROUW, Myriam PANNECOUQUE, Christophe SNOECK, Robert ANDREI, Graciela BALZARINI, Jan CLERCQ, Erik DE FAUVELLE, Florence ENGUEHARD, Cécile GUEIFFIER, Alain |
| description | This work reports the synthesis and the antiviral activities of 3-benzamido, 3-phenylureido and 3-phenyl-thioureido derivatives in the imidazo[1,2-a]pyridine series. The structure was proven by NMR spectroscopy. The synthesized compounds were evaluated against a large number of viruses. The 3-phenylthioureido derivative 7 showed moderate activity against human cytomegalovirus (HCMV) in vitro. The crystallographic data for 8 are also reported and explain the absence of activity against human immunodeficiency virus (HIV). |
| doi_str_mv | 10.1248/cpb.49.1631 |
| format | Article |
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The structure was proven by NMR spectroscopy. The synthesized compounds were evaluated against a large number of viruses. The 3-phenylthioureido derivative 7 showed moderate activity against human cytomegalovirus (HCMV) in vitro. The crystallographic data for 8 are also reported and explain the absence of activity against human immunodeficiency virus (HIV).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.49.1631</identifier><identifier>PMID: 11767086</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Anti-HIV Agents - chemical synthesis ; Anti-HIV Agents - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - pharmacology ; Biological and medical sciences ; Cells, Cultured ; crystallographic data ; Crystallography, X-Ray ; cytomegalovirus ; Cytomegalovirus - drug effects ; Humans ; imidazo[1,2-a]pyridine ; Imidazoles - chemical synthesis ; Imidazoles - pharmacology ; Magnetic Resonance Spectroscopy ; Medical sciences ; Models, Molecular ; Pharmacology. Drug treatments ; phenylthioureido ; Phenylurea Compounds - chemical synthesis ; Phenylurea Compounds - pharmacology ; Structure-Activity Relationship ; Thiourea - analogs & derivatives ; Thiourea - chemical synthesis ; Thiourea - pharmacology ; Viral Plaque Assay</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2001, Vol.49(12), pp.1631-1635</ispartof><rights>2001 The Pharmaceutical Society of Japan</rights><rights>2002 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2001</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c576t-dc904d58410d01a0321e12da377b9179704162c047f8227436242b9f6aea336e3</citedby><cites>FETCH-LOGICAL-c576t-dc904d58410d01a0321e12da377b9179704162c047f8227436242b9f6aea336e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13393817$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11767086$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>CHAOUNI-BENABDALLAH, Aziz</creatorcontrib><creatorcontrib>GALTIER, Christophe</creatorcontrib><creatorcontrib>ALLOUCHI, Hassan</creatorcontrib><creatorcontrib>KHERBECHE, Abdelak</creatorcontrib><creatorcontrib>CHAVIGNON, Olivier</creatorcontrib><creatorcontrib>TEULADE, Jean-Claude</creatorcontrib><creatorcontrib>WITVROUW, Myriam</creatorcontrib><creatorcontrib>PANNECOUQUE, Christophe</creatorcontrib><creatorcontrib>SNOECK, Robert</creatorcontrib><creatorcontrib>ANDREI, Graciela</creatorcontrib><creatorcontrib>BALZARINI, Jan</creatorcontrib><creatorcontrib>CLERCQ, Erik DE</creatorcontrib><creatorcontrib>FAUVELLE, Florence</creatorcontrib><creatorcontrib>ENGUEHARD, Cécile</creatorcontrib><creatorcontrib>GUEIFFIER, Alain</creatorcontrib><title>3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>This work reports the synthesis and the antiviral activities of 3-benzamido, 3-phenylureido and 3-phenyl-thioureido derivatives in the imidazo[1,2-a]pyridine series. The structure was proven by NMR spectroscopy. The synthesized compounds were evaluated against a large number of viruses. The 3-phenylthioureido derivative 7 showed moderate activity against human cytomegalovirus (HCMV) in vitro. The crystallographic data for 8 are also reported and explain the absence of activity against human immunodeficiency virus (HIV).</description><subject>Anti-HIV Agents - chemical synthesis</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cells, Cultured</subject><subject>crystallographic data</subject><subject>Crystallography, X-Ray</subject><subject>cytomegalovirus</subject><subject>Cytomegalovirus - drug effects</subject><subject>Humans</subject><subject>imidazo[1,2-a]pyridine</subject><subject>Imidazoles - chemical synthesis</subject><subject>Imidazoles - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>phenylthioureido</subject><subject>Phenylurea Compounds - chemical synthesis</subject><subject>Phenylurea Compounds - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Thiourea - analogs & derivatives</subject><subject>Thiourea - chemical synthesis</subject><subject>Thiourea - pharmacology</subject><subject>Viral Plaque Assay</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1v1DAQxS0EokvhxB1FQnBps3g8jp0c21I-pEpwaE8IWRPHab3KJls7u1L71-OwUVfiwsXP4_npjTyPsbfAlyBk-clu6qWslqAQnrEFoNR5IQQ-ZwvOeZULVHjEXsW44lwUXONLdgSglealWrAa83PXP9LaN8NpdhNc0oz6Jru-88P2b-lTjx6HX3Aqcvq9eQi-8b3LPrvgdzT6nYsZxeznMLp-9NRlZ0l2Pky32_QUX7MXLXXRvZn1mN18uby--JZf_fj6_eLsKreFVmPe2IrLpigl8IYDcRTgQDSEWtcV6EpzCUpYLnVbCqElKiFFXbWKHCEqh8fs4953E4b7rYujWftoXddR74ZtNHrahJTivyCUkstClAl8_w-4Sjvp0ycMSMURtCwnu5M9ZcMQY3Ct2QS_pvBggJspIZMSMrIyU0KJfjd7buu1aw7sHEkCPswARUtdG6i3Ph44xApL0Ik733OrONKtewIojN527mmomM9p-qF5R8G4Hv8Alj-t-Q</recordid><startdate>20011201</startdate><enddate>20011201</enddate><creator>CHAOUNI-BENABDALLAH, Aziz</creator><creator>GALTIER, Christophe</creator><creator>ALLOUCHI, Hassan</creator><creator>KHERBECHE, Abdelak</creator><creator>CHAVIGNON, Olivier</creator><creator>TEULADE, Jean-Claude</creator><creator>WITVROUW, Myriam</creator><creator>PANNECOUQUE, Christophe</creator><creator>SNOECK, Robert</creator><creator>ANDREI, Graciela</creator><creator>BALZARINI, Jan</creator><creator>CLERCQ, Erik DE</creator><creator>FAUVELLE, Florence</creator><creator>ENGUEHARD, Cécile</creator><creator>GUEIFFIER, Alain</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20011201</creationdate><title>3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents</title><author>CHAOUNI-BENABDALLAH, Aziz ; GALTIER, Christophe ; ALLOUCHI, Hassan ; KHERBECHE, Abdelak ; CHAVIGNON, Olivier ; TEULADE, Jean-Claude ; WITVROUW, Myriam ; PANNECOUQUE, Christophe ; SNOECK, Robert ; ANDREI, Graciela ; BALZARINI, Jan ; CLERCQ, Erik DE ; FAUVELLE, Florence ; ENGUEHARD, Cécile ; GUEIFFIER, Alain</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c576t-dc904d58410d01a0321e12da377b9179704162c047f8227436242b9f6aea336e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Anti-HIV Agents - chemical synthesis</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cells, Cultured</topic><topic>crystallographic data</topic><topic>Crystallography, X-Ray</topic><topic>cytomegalovirus</topic><topic>Cytomegalovirus - drug effects</topic><topic>Humans</topic><topic>imidazo[1,2-a]pyridine</topic><topic>Imidazoles - chemical synthesis</topic><topic>Imidazoles - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>phenylthioureido</topic><topic>Phenylurea Compounds - chemical synthesis</topic><topic>Phenylurea Compounds - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Thiourea - analogs & derivatives</topic><topic>Thiourea - chemical synthesis</topic><topic>Thiourea - pharmacology</topic><topic>Viral Plaque Assay</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>CHAOUNI-BENABDALLAH, Aziz</creatorcontrib><creatorcontrib>GALTIER, Christophe</creatorcontrib><creatorcontrib>ALLOUCHI, Hassan</creatorcontrib><creatorcontrib>KHERBECHE, Abdelak</creatorcontrib><creatorcontrib>CHAVIGNON, Olivier</creatorcontrib><creatorcontrib>TEULADE, Jean-Claude</creatorcontrib><creatorcontrib>WITVROUW, Myriam</creatorcontrib><creatorcontrib>PANNECOUQUE, Christophe</creatorcontrib><creatorcontrib>SNOECK, Robert</creatorcontrib><creatorcontrib>ANDREI, Graciela</creatorcontrib><creatorcontrib>BALZARINI, Jan</creatorcontrib><creatorcontrib>CLERCQ, Erik DE</creatorcontrib><creatorcontrib>FAUVELLE, Florence</creatorcontrib><creatorcontrib>ENGUEHARD, Cécile</creatorcontrib><creatorcontrib>GUEIFFIER, Alain</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>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>CHAOUNI-BENABDALLAH, Aziz</au><au>GALTIER, Christophe</au><au>ALLOUCHI, Hassan</au><au>KHERBECHE, Abdelak</au><au>CHAVIGNON, Olivier</au><au>TEULADE, Jean-Claude</au><au>WITVROUW, Myriam</au><au>PANNECOUQUE, Christophe</au><au>SNOECK, Robert</au><au>ANDREI, Graciela</au><au>BALZARINI, Jan</au><au>CLERCQ, Erik DE</au><au>FAUVELLE, Florence</au><au>ENGUEHARD, Cécile</au><au>GUEIFFIER, Alain</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2001-12-01</date><risdate>2001</risdate><volume>49</volume><issue>12</issue><spage>1631</spage><epage>1635</epage><pages>1631-1635</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>This work reports the synthesis and the antiviral activities of 3-benzamido, 3-phenylureido and 3-phenyl-thioureido derivatives in the imidazo[1,2-a]pyridine series. The structure was proven by NMR spectroscopy. The synthesized compounds were evaluated against a large number of viruses. The 3-phenylthioureido derivative 7 showed moderate activity against human cytomegalovirus (HCMV) in vitro. The crystallographic data for 8 are also reported and explain the absence of activity against human immunodeficiency virus (HIV).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11767086</pmid><doi>10.1248/cpb.49.1631</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Anti-HIV Agents - chemical synthesis Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - pharmacology Biological and medical sciences Cells, Cultured crystallographic data Crystallography, X-Ray cytomegalovirus Cytomegalovirus - drug effects Humans imidazo[1,2-a]pyridine Imidazoles - chemical synthesis Imidazoles - pharmacology Magnetic Resonance Spectroscopy Medical sciences Models, Molecular Pharmacology. Drug treatments phenylthioureido Phenylurea Compounds - chemical synthesis Phenylurea Compounds - pharmacology Structure-Activity Relationship Thiourea - analogs & derivatives Thiourea - chemical synthesis Thiourea - pharmacology Viral Plaque Assay |
| title | 3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents |
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