Molecules (Apr 2008)

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

  • Man-Chin Chung,
  • Vladimir Constantino Gomes Heleno,
  • Leila Aley Tavares,
  • Elisangela Fabiana Boffo,
  • Antonio Gilberto Ferreira,
  • Elizabeth Igne Ferreira,
  • Renato Farina Menegon,
  • Lorena Blau

DOI
https://doi.org/10.3390/molecules13040841
Journal volume & issue
Vol. 13, no. 4
pp. 841 – 854

Abstract

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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.

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