Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2008 |
| Outros Autores: | , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da UNESP |
| Texto Completo: | http://dx.doi.org/10.3390/molecules13040841 http://hdl.handle.net/11449/130528 |
Resumo: | We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4″- nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino] -diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0] oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino) pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl) amino]- 5-dioxide (7) are also described, together with their total 1H- and 13C-NMR assignments. © 2008 by MDPI. |
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Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches1H, 13C and 2D NMRADEPTCancerCephalosporinProdrugcephalosporin derivativeprimaquineprodrugchemistryisomerismnuclear magnetic resonance spectroscopysynthesisCephalosporinsIsomerismMagnetic Resonance SpectroscopyPrimaquineProdrugsWe report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4″- nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino] -diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0] oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino) pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl) amino]- 5-dioxide (7) are also described, together with their total 1H- and 13C-NMR assignments. © 2008 by MDPI.Departamento de Fármacos e Medicamentos Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista, CP 502, 14801-902, Araraquara, SPDepartamento de Farmácia Faculdade de Ciências Farmacêuticas Universidade de São Paulo, CP 66083, 05389-970, São Paulo, SPDepartamento de Química Centro de Ciências Exatas e Tecnológicas Universidade Federal de São Carlos, CP 676, 13565-905, São Carlos, SPNúcleo de Pesquisas em Ciências Exatas e Tecnológicas Universidade de Franca, CP 82, 14404-600, Franca, SPDepartamento de Fármacos e Medicamentos Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista, CP 502, 14801-902, Araraquara, SPMolecular Diversity Preservation IntUniversidade Estadual Paulista (Unesp)Universidade de São Paulo (USP)Universidade Federal de São Carlos (UFSCar)Universidade de FrancaBlau, Lorena [UNESP]Menegon, Renato Farina [UNESP]Ferreira, Elizabeth IgneFerreira, Antonio GilbertoBoffo, Elisangela FabianaTavares, Leila AleyHeleno, Vladimir Constantino GomesChung, Man-Chin [UNESP]2014-05-27T11:23:31Z2014-05-27T11:23:31Z2008-04-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article841-854application/pdfhttp://dx.doi.org/10.3390/molecules13040841Molecules. Basel: Molecular Diversity Preservation Int, v. 13, n. 4, p. 841-854, 2008.1420-3049http://hdl.handle.net/11449/13052810.3390/molecules13040841WOS:0002555159000152-s2.0-430491670952-s2.0-43049167095.pdf97343336079754130000-0003-4141-0455Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengMolecules3.0980,855info:eu-repo/semantics/openAccess2023-11-23T06:14:21Zoai:repositorio.unesp.br:11449/130528Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-11-23T06:14:21Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
| dc.title.none.fl_str_mv |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches |
| title |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches |
| spellingShingle |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches Blau, Lorena [UNESP] 1H, 13C and 2D NMR ADEPT Cancer Cephalosporin Prodrug cephalosporin derivative primaquine prodrug chemistry isomerism nuclear magnetic resonance spectroscopy synthesis Cephalosporins Isomerism Magnetic Resonance Spectroscopy Primaquine Prodrugs |
| title_short |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches |
| title_full |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches |
| title_fullStr |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches |
| title_full_unstemmed |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches |
| title_sort |
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches |
| author |
Blau, Lorena [UNESP] |
| author_facet |
Blau, Lorena [UNESP] Menegon, Renato Farina [UNESP] Ferreira, Elizabeth Igne Ferreira, Antonio Gilberto Boffo, Elisangela Fabiana Tavares, Leila Aley Heleno, Vladimir Constantino Gomes Chung, Man-Chin [UNESP] |
| author_role |
author |
| author2 |
Menegon, Renato Farina [UNESP] Ferreira, Elizabeth Igne Ferreira, Antonio Gilberto Boffo, Elisangela Fabiana Tavares, Leila Aley Heleno, Vladimir Constantino Gomes Chung, Man-Chin [UNESP] |
| author2_role |
author author author author author author author |
| dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) Universidade de São Paulo (USP) Universidade Federal de São Carlos (UFSCar) Universidade de Franca |
| dc.contributor.author.fl_str_mv |
Blau, Lorena [UNESP] Menegon, Renato Farina [UNESP] Ferreira, Elizabeth Igne Ferreira, Antonio Gilberto Boffo, Elisangela Fabiana Tavares, Leila Aley Heleno, Vladimir Constantino Gomes Chung, Man-Chin [UNESP] |
| dc.subject.por.fl_str_mv |
1H, 13C and 2D NMR ADEPT Cancer Cephalosporin Prodrug cephalosporin derivative primaquine prodrug chemistry isomerism nuclear magnetic resonance spectroscopy synthesis Cephalosporins Isomerism Magnetic Resonance Spectroscopy Primaquine Prodrugs |
| topic |
1H, 13C and 2D NMR ADEPT Cancer Cephalosporin Prodrug cephalosporin derivative primaquine prodrug chemistry isomerism nuclear magnetic resonance spectroscopy synthesis Cephalosporins Isomerism Magnetic Resonance Spectroscopy Primaquine Prodrugs |
| description |
We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4″- nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino] -diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0] oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino) pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl) amino]- 5-dioxide (7) are also described, together with their total 1H- and 13C-NMR assignments. © 2008 by MDPI. |
| publishDate |
2008 |
| dc.date.none.fl_str_mv |
2008-04-01 2014-05-27T11:23:31Z 2014-05-27T11:23:31Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.3390/molecules13040841 Molecules. Basel: Molecular Diversity Preservation Int, v. 13, n. 4, p. 841-854, 2008. 1420-3049 http://hdl.handle.net/11449/130528 10.3390/molecules13040841 WOS:000255515900015 2-s2.0-43049167095 2-s2.0-43049167095.pdf 9734333607975413 0000-0003-4141-0455 |
| url |
http://dx.doi.org/10.3390/molecules13040841 http://hdl.handle.net/11449/130528 |
| identifier_str_mv |
Molecules. Basel: Molecular Diversity Preservation Int, v. 13, n. 4, p. 841-854, 2008. 1420-3049 10.3390/molecules13040841 WOS:000255515900015 2-s2.0-43049167095 2-s2.0-43049167095.pdf 9734333607975413 0000-0003-4141-0455 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
Molecules 3.098 0,855 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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841-854 application/pdf |
| dc.publisher.none.fl_str_mv |
Molecular Diversity Preservation Int |
| publisher.none.fl_str_mv |
Molecular Diversity Preservation Int |
| dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
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Universidade Estadual Paulista (UNESP) |
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UNESP |
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UNESP |
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Repositório Institucional da UNESP |
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Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
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