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We describe the synthesis of tert-butyl esters of 3-(2-hydroxybenzoyloxy)methyl-, 3-(dihydroxybenzoyloxy)methyl-, and 3-(diacetoxybenzoyloxy)methyl-7α-chlorocephalosporanic acid sulfones by reaction of tert-butyl ester of 3-bromomethyl-7α-chlorocephalosporanic acid sulfone with salts of hydroxy- and acetoxy-substituted benzoic acids. We have investigated the elastase-inhibiting properties of the compounds obtained and also their in vitrocytotoxic activity.

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.

A method has been developed for the preparation of tert-butoxycarbonylandno-3-hydroxymethylceph-2-em-4-carboxylic acid, which is an intermediate for the preparation of new antibiotic derivatives with antibacterial, anti-inflammatory, or antitumor activity.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.