Massachusetts Institute of Technology

Thomas J Commons

John C Sheehan

Young-Sek Lo

Biologically active sulfur analogs of 6-aminopenicillanic acid having a nucleophile substituted in the 6- position are made by reacting a sulfenyl chloride with esters of diazopenicillanic acid. Biologically active sulfur analogs of 7-aminocephalosporanic acid having a nucleophile substituted in the 7- position are analogously made by reacting a sulfenyl chloride with esters of 7-diazocephalosporanic acid. Deacetoxycephalosporins can be formed from the corresponding analog of 6-aminopenicillanic acid and derivations thereof, by sulfoxide rearrangement of the thiazolidine ring of penicillins to the dihydrothiazine ring of cephalosporins. These nucleophile substituted sulfur analogs of penicillins and cephalosporins are new antibacterial agents and display antibacterial activity against a variety of microorganisms.

Sulphur analogs of cephalosporins having a nucleophile substituted in

Biologically active sulfur analogs of 6-aminopenicillanic acid having a nucleophile substituted in the 6-position are made by reacting a sulfenyl chloride with esters of diazopenicillanic acid. Biologically active sulfur analogs of 7-aminocephalosporanic acid having a nucleophile substituted in the 7-position are analogously made by reacting a sulfenyl chloride with esters of 7-diazocephalosporanic acid. Deacetoxycephalosporins can be formed from the corresponding analog of 6-aminopenicillanic acid and derivations thereof, by sulfoxide rearrangement of the thiazolidine ring of penicillins to the dihydrothiazine ring of cephalosporins. These nucleophile substituted sulfur analogs of penicillins and cephalosporins are new antibacterial agents and display antibacterial activity against a variety of microorganisms.

Sulphur analogs of penicillins having a nucleophile substituted in the 6

Sulfur analogs of 6-aminopenicillanic acid and biologically active derivatives thereof are formed in a photochemical reaction of the esters of 6-diazopenicillanic acid with thiol compounds. Sulfur analogs of 7-aminocephalosporanic acid and biologically active derivatives thereof may be analogously formed in a photochemical reaction of the esters of 7-diazocephalosporanic acid with thiol compounds, or preferably, are formed from the corresponding sulfur analogs of 6-aminopenicillanic acid and derivatives thereof, through sulfoxide rearrangement of the thiazolidine ring of penicillins to the dihydrothiazine ring system of cephalosporins. These sulfur analogs of penicillins and cephalosporins are new antibacterial agents and display antibacterial activity against a wide variety of organisms.

Growing community of inventors

Boston, MA, United States of America

Thomas J Commons