CEPHALOSPORINS CONTAINING CARBONATE FUNCTIONS AT POSITIONS 3 AND 7

Authors

  • Г. Вейнберг Latvian Institute of Organic Synthesis
  • М. Ворона Latvian Institute of Organic Synthesis
  • Н. Григан Latvian Institute of Organic Synthesis
  • И. Канепе Latvian Institute of Organic Synthesis
  • И. Шестакова Latvian Institute of Organic Synthesis
  • А. Страков Latvian Institute of Organic Synthesis
  • Э. Лукевиц Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/249

Keywords:

sulfones of 7-alkoxycarbonyloxy-substituted cephalosporanic acids tert-butyl esters, sulfones of 7-chloro- and 7-alkylidene-substituted 3-alkoxycarbonyloxymethylcephalosporanic acids tert-butyl esters, elastase inhibitors

Abstract

Sulfones of 7β-alkoxycarbonyloxy-substituted cephalosporanic acid tert-butyl esters were synthesized by reduction of 7-oxocephalosporanic acid tert-butyl ester, acylation of the intermediate 7β-hydroxycephalosporanate with 2,2,2-trichloroethyl chloroformate or di-tert-butyl pyrocarbonate, and oxidation of the sulfur atom. Sulfones of 7α-chloro- and 7-alkylidene-substituted 3 alkoxycarbonyloxymethylcephalosporanic acid tert-butyl esters were obtained by replacement of the bromine atom in tert-butyl 3-bromomethylcephalosporanates with hydroxy group and acylation of the latter with chlorocarbonic esters. The cytotoxic activity of the synthesized substances was studied in vitro and also their ability to inhibit elastase.

Authors: G. Veinberg, M. Vorona, N. Grigan, I. Kanepe, I. Shestakova, A. Strakov and E. Lukevics.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (6), pp 744-750

http://link.springer.com/article/10.1007/BF02297686

 

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Published

2013-02-05

Issue

No. 6 (2000)

Section

Original Papers