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

Molecules. 2008 Apr 10;13(4):841-54. doi: 10.3390/molecules13040841.

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 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 (1)H- and (13)C-NMR assignments.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cephalosporins / chemical synthesis*
  • Cephalosporins / chemistry
  • Cephalosporins / therapeutic use*
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Primaquine / chemical synthesis
  • Primaquine / chemistry
  • Prodrugs / chemical synthesis
  • Prodrugs / chemistry

Substances

  • Cephalosporins
  • Prodrugs
  • Primaquine