6-Sulfur analogs of penicillins and cephalosporins

Details 6-Sulfur analogs of penicillins and cephalosporins 6-Sulfur analogs of penicillins and cephalosporins

1976-08-09

1978-06-06

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

204158R, 2602391, 424246, 424270, 424271, 544 18, 544 22, 544 26, 544 28, 544 29, C07D49900, C07D50100, C07D50104, C07D50110

Patent

active

040936252

ABSTRACT:
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.

REFERENCES:
slusarchyk et al., J. Org. Chem., vol. 38, pp. 943-949, (1973).
Jen et al., J. Org. Chem., vol. 38, pp. 2857-2859, (1973).

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