The cephalosporin C nucleus (7-aminocephalosporanic acid) and some of its derivatives

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Abstract
Treatment of cephalosporin C with dilute acid, at room temperature, has produced, in small yield, a compound whose properties correspond with those of the cephalosporin C nucleus (7-aminocephalosporanic acid). This compound is formed by the hydrolytic removal of the D-( [sigma] -atninoadipoyl) side chain of cephalosporin C. 7-Amino-cephalosporanic acid showed no antibacterial activity under the test conditions used, but formed active N-acyl derivatives. A purified sample of 7-aminocephalosporanic acid yielded an N-phenylacetyl derivative whose activity against Staphylococcus aureus was about 100 times that of cephalosporin C. Treatment of cephalosporin C with dilute acid also yields the nucleus of cephalosporin Cc. The formation of this compound involves hydrolysis of an acetoxy group and subsequent lactonization, as well as removal of the side chain. The same compound is formed on hydrolysis of cephalosporin Cc. Hydrolysis of cephalosporin CA. (pyridine) in dilute acid yields the nucleus of cephalosporin Ca (pyridine). This nucleus is also formed when 7-aminocephalosporanic acid reacts with aqueous pyridine.