Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches

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 carr...

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Detalles Bibliográficos
Autores: 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]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2008
País:Brasil
Institución:Universidade Estadual Paulista (UNESP)
Repositorio:Repositório Institucional da UNESP
Idioma:inglés
OAI Identifier:oai:repositorio.unesp.br:11449/130528
Acceso en línea:http://dx.doi.org/10.3390/molecules13040841
http://hdl.handle.net/11449/130528
Access Level:acceso abierto
Palabra clave: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
Descripción
Sumario: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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