Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the N′-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide Groups at C-2
A series of novel benzo[4,5]canthin-6-ones, bearing the N′-(substituted benzylidene)-carbohydrazide (11a-e) and N-alkylcarboxamide (13a-g) moieties at position-2, were synthesized and screened for their in vitro antitumor activity, against seven human cancer cell lines, and for antitrypanosomal and...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2012/11/01, Vol.60(11), pp.1372-1379 |
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| creator | Camila Mareco Bento Leite Silva Garcia, Francielle Pelegrin Jean Henrique da Silva Rodrigues Nakamura, Celso Vataru Ueda-Nakamura, Tania Meyer, Emerson Ana Lucia Tasca Gois Ruiz Foglio, Mary Ann Carvalho, João Ernesto de Costa, Willian Ferreira da Sarragiotto, Maria Helena |
| description | A series of novel benzo[4,5]canthin-6-ones, bearing the N′-(substituted benzylidene)-carbohydrazide (11a-e) and N-alkylcarboxamide (13a-g) moieties at position-2, were synthesized and screened for their in vitro antitumor activity, against seven human cancer cell lines, and for antitrypanosomal and antileishmanial activities against Trypanosoma cruzi and Leishmania amazonensis. The results indicated that N-methylpiperazyl-6-oxobenzo[4,5]canthine-2-carboxamide (13f) displayed potent antitumor activity with IC50 values in the range of 1.15-8.46 µM for all cell lines tested. Compounds 13f and 13g bearing an N-methylpiperazylcarboxamide and N-morpholylcarboxamide at C-2, respectively, showed potent activities towards both Trypanosoma cruzi and Leishmania amazonensis parasites, with IC50 in the range of 0.4 to 16.70 µM. |
| doi_str_mv | 10.1248/cpb.c12-00356 |
| format | Article |
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The results indicated that N-methylpiperazyl-6-oxobenzo[4,5]canthine-2-carboxamide (13f) displayed potent antitumor activity with IC50 values in the range of 1.15-8.46 µM for all cell lines tested. Compounds 13f and 13g bearing an N-methylpiperazylcarboxamide and N-morpholylcarboxamide at C-2, respectively, showed potent activities towards both Trypanosoma cruzi and Leishmania amazonensis parasites, with IC50 in the range of 0.4 to 16.70 µM.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c12-00356</identifier><identifier>PMID: 23124560</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>antileishmanial activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; antitrypanosomal activity ; antitumor activity ; benzocanthinone ; Benzylidene Compounds - chemical synthesis ; Benzylidene Compounds - chemistry ; Benzylidene Compounds - pharmacology ; benzylidenecarbohydrazide ; Carbolines ; carboxamide ; Cell Line, Tumor ; Chagas Disease - drug therapy ; Humans ; Indole Alkaloids ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Inhibitory Concentration 50 ; Leishmania - drug effects ; Leishmaniasis - drug therapy ; Naphthyridines - chemical synthesis ; Naphthyridines - chemistry ; Naphthyridines - pharmacology ; Neoplasms - drug therapy ; Trypanocidal Agents - chemical synthesis ; Trypanocidal Agents - chemistry ; Trypanocidal Agents - pharmacology ; Trypanosoma cruzi - drug effects</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2012/11/01, Vol.60(11), pp.1372-1379</ispartof><rights>2012 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2012</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c610t-7493a26bf1cfa6a04e41937f351782fbb7298f8ebf5948a616cc330a5399adc83</citedby><cites>FETCH-LOGICAL-c610t-7493a26bf1cfa6a04e41937f351782fbb7298f8ebf5948a616cc330a5399adc83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23124560$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Camila Mareco Bento Leite Silva</creatorcontrib><creatorcontrib>Garcia, Francielle Pelegrin</creatorcontrib><creatorcontrib>Jean Henrique da Silva Rodrigues</creatorcontrib><creatorcontrib>Nakamura, Celso Vataru</creatorcontrib><creatorcontrib>Ueda-Nakamura, Tania</creatorcontrib><creatorcontrib>Meyer, Emerson</creatorcontrib><creatorcontrib>Ana Lucia Tasca Gois Ruiz</creatorcontrib><creatorcontrib>Foglio, Mary Ann</creatorcontrib><creatorcontrib>Carvalho, João Ernesto de</creatorcontrib><creatorcontrib>Costa, Willian Ferreira da</creatorcontrib><creatorcontrib>Sarragiotto, Maria Helena</creatorcontrib><creatorcontrib>Biologicas e Agricolas (CPQBA</creatorcontrib><creatorcontrib>Departamento de Quimica</creatorcontrib><creatorcontrib>Bloco B- Sala CCS</creatorcontrib><creatorcontrib>Centro Pluridisciplinar de Pesquisas Quimicas</creatorcontrib><creatorcontrib>Departamento de Ciencias Basicas da Saude</creatorcontrib><creatorcontrib>Universidade Estadual de Maringa</creatorcontrib><creatorcontrib>Universidade Estadual de Maringq</creatorcontrib><creatorcontrib>Laboratorio de Inovacao Tecnologica no Desenvolvimento de Farmacos e Cosmeticos</creatorcontrib><creatorcontrib>Universidade Estadual de Campinas</creatorcontrib><title>Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the N′-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide Groups at C-2</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of novel benzo[4,5]canthin-6-ones, bearing the N′-(substituted benzylidene)-carbohydrazide (11a-e) and N-alkylcarboxamide (13a-g) moieties at position-2, were synthesized and screened for their in vitro antitumor activity, against seven human cancer cell lines, and for antitrypanosomal and antileishmanial activities against Trypanosoma cruzi and Leishmania amazonensis. The results indicated that N-methylpiperazyl-6-oxobenzo[4,5]canthine-2-carboxamide (13f) displayed potent antitumor activity with IC50 values in the range of 1.15-8.46 µM for all cell lines tested. Compounds 13f and 13g bearing an N-methylpiperazylcarboxamide and N-morpholylcarboxamide at C-2, respectively, showed potent activities towards both Trypanosoma cruzi and Leishmania amazonensis parasites, with IC50 in the range of 0.4 to 16.70 µM.</description><subject>antileishmanial activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>antitrypanosomal activity</subject><subject>antitumor activity</subject><subject>benzocanthinone</subject><subject>Benzylidene Compounds - chemical synthesis</subject><subject>Benzylidene Compounds - chemistry</subject><subject>Benzylidene Compounds - pharmacology</subject><subject>benzylidenecarbohydrazide</subject><subject>Carbolines</subject><subject>carboxamide</subject><subject>Cell Line, Tumor</subject><subject>Chagas Disease - drug therapy</subject><subject>Humans</subject><subject>Indole Alkaloids</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Inhibitory Concentration 50</subject><subject>Leishmania - drug effects</subject><subject>Leishmaniasis - drug therapy</subject><subject>Naphthyridines - chemical synthesis</subject><subject>Naphthyridines - chemistry</subject><subject>Naphthyridines - pharmacology</subject><subject>Neoplasms - drug therapy</subject><subject>Trypanocidal Agents - chemical synthesis</subject><subject>Trypanocidal Agents - chemistry</subject><subject>Trypanocidal Agents - pharmacology</subject><subject>Trypanosoma cruzi - drug effects</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>eNpdUc1u1DAYjBCILoUjVxSJS5Hq4p_EiY_bBQpSVQ6FE0LWF8fpeknsrZ0g0hPPxBPwLDwJTnbZSlz8WTPzzXzSJMlzgs8IzcrXaludKUIRxiznD5IFYVmBckrZw2SBMRaIMs6OkichbDCmOS7Y4-SIsribc7xIfl-Ptl_rYMJpurS96YfO-f3Xj1uwLrgO2hRsPYOtNmHdgTURW6refDe90SF1TXqu7Z37kp3mXxVES2MRR85G7lyDN_YmjTHp1Z-fv9DJ9VCFKarXdVrFtbE1tbb6FVLgK7ceaw93EZlDr9Cy_Ta2M_MDugm-8G7YhhT6dIXo0-RRA23Qz_bzOPn87u2n1Xt0-fHiw2p5iRQnuEdFJhhQXjVENcABZzojghUNy0lR0qaqCirKptRVk4usBE64UoxhyJkQUKuSHScnO9-td7eDDr3sTFC6bcFqNwRJCBOcFCQXUfryP-nGDd7G6yTJOM7yEotJhXYq5V0IXjdy600HfpQEy6laGauVsVo5Vxv1L_auQ9Xp-qD-12UUXOwEkTUKWmdbY_V9tgqFWuvOSIpnU44JiSOThBV0egQpc8HF5PRm57QJPdzoQxT43qhWz4fxeCSZ3sOF9_QavNSW_QWLRNED</recordid><startdate>20121101</startdate><enddate>20121101</enddate><creator>Camila Mareco Bento Leite Silva</creator><creator>Garcia, Francielle Pelegrin</creator><creator>Jean Henrique da Silva Rodrigues</creator><creator>Nakamura, Celso Vataru</creator><creator>Ueda-Nakamura, Tania</creator><creator>Meyer, Emerson</creator><creator>Ana Lucia Tasca Gois Ruiz</creator><creator>Foglio, Mary Ann</creator><creator>Carvalho, João Ernesto de</creator><creator>Costa, Willian Ferreira da</creator><creator>Sarragiotto, Maria Helena</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20121101</creationdate><title>Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the N′-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide Groups at C-2</title><author>Camila Mareco Bento Leite Silva ; Garcia, Francielle Pelegrin ; Jean Henrique da Silva Rodrigues ; Nakamura, Celso Vataru ; Ueda-Nakamura, Tania ; Meyer, Emerson ; Ana Lucia Tasca Gois Ruiz ; Foglio, Mary Ann ; Carvalho, João Ernesto de ; Costa, Willian Ferreira da ; Sarragiotto, Maria Helena</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c610t-7493a26bf1cfa6a04e41937f351782fbb7298f8ebf5948a616cc330a5399adc83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>antileishmanial activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>antitrypanosomal activity</topic><topic>antitumor activity</topic><topic>benzocanthinone</topic><topic>Benzylidene Compounds - chemical synthesis</topic><topic>Benzylidene Compounds - chemistry</topic><topic>Benzylidene Compounds - pharmacology</topic><topic>benzylidenecarbohydrazide</topic><topic>Carbolines</topic><topic>carboxamide</topic><topic>Cell Line, Tumor</topic><topic>Chagas Disease - drug therapy</topic><topic>Humans</topic><topic>Indole Alkaloids</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Inhibitory Concentration 50</topic><topic>Leishmania - drug effects</topic><topic>Leishmaniasis - drug therapy</topic><topic>Naphthyridines - chemical synthesis</topic><topic>Naphthyridines - chemistry</topic><topic>Naphthyridines - pharmacology</topic><topic>Neoplasms - drug therapy</topic><topic>Trypanocidal Agents - chemical synthesis</topic><topic>Trypanocidal Agents - chemistry</topic><topic>Trypanocidal Agents - pharmacology</topic><topic>Trypanosoma cruzi - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Camila Mareco Bento Leite Silva</creatorcontrib><creatorcontrib>Garcia, Francielle Pelegrin</creatorcontrib><creatorcontrib>Jean Henrique da Silva Rodrigues</creatorcontrib><creatorcontrib>Nakamura, Celso Vataru</creatorcontrib><creatorcontrib>Ueda-Nakamura, Tania</creatorcontrib><creatorcontrib>Meyer, Emerson</creatorcontrib><creatorcontrib>Ana Lucia Tasca Gois Ruiz</creatorcontrib><creatorcontrib>Foglio, Mary Ann</creatorcontrib><creatorcontrib>Carvalho, João Ernesto de</creatorcontrib><creatorcontrib>Costa, Willian Ferreira da</creatorcontrib><creatorcontrib>Sarragiotto, Maria Helena</creatorcontrib><creatorcontrib>Biologicas e Agricolas (CPQBA</creatorcontrib><creatorcontrib>Departamento de Quimica</creatorcontrib><creatorcontrib>Bloco B- Sala CCS</creatorcontrib><creatorcontrib>Centro Pluridisciplinar de Pesquisas Quimicas</creatorcontrib><creatorcontrib>Departamento de Ciencias Basicas da Saude</creatorcontrib><creatorcontrib>Universidade Estadual de Maringa</creatorcontrib><creatorcontrib>Universidade Estadual de Maringq</creatorcontrib><creatorcontrib>Laboratorio de Inovacao Tecnologica no Desenvolvimento de Farmacos e Cosmeticos</creatorcontrib><creatorcontrib>Universidade Estadual de Campinas</creatorcontrib><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>Camila Mareco Bento Leite Silva</au><au>Garcia, Francielle Pelegrin</au><au>Jean Henrique da Silva Rodrigues</au><au>Nakamura, Celso Vataru</au><au>Ueda-Nakamura, Tania</au><au>Meyer, Emerson</au><au>Ana Lucia Tasca Gois Ruiz</au><au>Foglio, Mary Ann</au><au>Carvalho, João Ernesto de</au><au>Costa, Willian Ferreira da</au><au>Sarragiotto, Maria Helena</au><aucorp>Biologicas e Agricolas (CPQBA</aucorp><aucorp>Departamento de Quimica</aucorp><aucorp>Bloco B- Sala CCS</aucorp><aucorp>Centro Pluridisciplinar de Pesquisas Quimicas</aucorp><aucorp>Departamento de Ciencias Basicas da Saude</aucorp><aucorp>Universidade Estadual de Maringa</aucorp><aucorp>Universidade Estadual de Maringq</aucorp><aucorp>Laboratorio de Inovacao Tecnologica no Desenvolvimento de Farmacos e Cosmeticos</aucorp><aucorp>Universidade Estadual de Campinas</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the N′-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide Groups at C-2</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2012-11-01</date><risdate>2012</risdate><volume>60</volume><issue>11</issue><spage>1372</spage><epage>1379</epage><pages>1372-1379</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A series of novel benzo[4,5]canthin-6-ones, bearing the N′-(substituted benzylidene)-carbohydrazide (11a-e) and N-alkylcarboxamide (13a-g) moieties at position-2, were synthesized and screened for their in vitro antitumor activity, against seven human cancer cell lines, and for antitrypanosomal and antileishmanial activities against Trypanosoma cruzi and Leishmania amazonensis. The results indicated that N-methylpiperazyl-6-oxobenzo[4,5]canthine-2-carboxamide (13f) displayed potent antitumor activity with IC50 values in the range of 1.15-8.46 µM for all cell lines tested. Compounds 13f and 13g bearing an N-methylpiperazylcarboxamide and N-morpholylcarboxamide at C-2, respectively, showed potent activities towards both Trypanosoma cruzi and Leishmania amazonensis parasites, with IC50 in the range of 0.4 to 16.70 µM.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>23124560</pmid><doi>10.1248/cpb.c12-00356</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 2012/11/01, Vol.60(11), pp.1372-1379 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | antileishmanial activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology antitrypanosomal activity antitumor activity benzocanthinone Benzylidene Compounds - chemical synthesis Benzylidene Compounds - chemistry Benzylidene Compounds - pharmacology benzylidenecarbohydrazide Carbolines carboxamide Cell Line, Tumor Chagas Disease - drug therapy Humans Indole Alkaloids Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Inhibitory Concentration 50 Leishmania - drug effects Leishmaniasis - drug therapy Naphthyridines - chemical synthesis Naphthyridines - chemistry Naphthyridines - pharmacology Neoplasms - drug therapy Trypanocidal Agents - chemical synthesis Trypanocidal Agents - chemistry Trypanocidal Agents - pharmacology Trypanosoma cruzi - drug effects |
| title | Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the N′-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide Groups at C-2 |
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