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

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

2, 3
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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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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