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Prodrugs for the Treatment of Neglected Diseases
Molecules 2008, 13(4), 841-854; doi:10.3390/molecules13040841
Article

Synthesis and Total 1H- and 13C-NMR Assignment of Cephem Derivatives for Use in ADEPT Approaches

1
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2, 3
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3,4,*  and 1,*
1 Departamento de Fármacos e Medicamentos, Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista, CP 502 – 14801-902, Araraquara, SP, Brazil 2 Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, CP 66083 – 05389-970, São Paulo, SP, Brazil 3 Departamento de Química, Centro de Ciências Exatas e Tecnológicas, Universidade Federal de São Carlos, CP 676 – 13565-905, São Carlos, SP, Brazil 4 Núcleo de Pesquisas em Ciências Exatas e Tecnológicas – Universidade de Franca, CP 82 – 14404-600, Franca, SP, Brazil
* Authors to whom correspondence should be addressed.
Received: 12 March 2008 / Revised: 6 April 2008 / Accepted: 7 April 2007 / Published: 10 April 2008
(This article belongs to the Special Issue Prodrugs)
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Abstract

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 cephalosporinderivative. This compound can be used as the carrier of a wide range of drugs containingan 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 alsodescribed, together with their total 1H- and 13C-NMR assignments.
Keywords: ADEPT; prodrug; cancer; cephalosporin; 1H; 13C and 2D NMR. ADEPT; prodrug; cancer; cephalosporin; 1H; 13C and 2D NMR.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Blau, L.; Menegon, R.F.; Ferreira, E.I.; Ferreira, A.G.; Boffo, E.F.; Tavares, L.A.; Heleno, V.C.G.; Chung, M.-C. Synthesis and Total 1H- and 13C-NMR Assignment of Cephem Derivatives for Use in ADEPT Approaches. Molecules 2008, 13, 841-854.

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