7/3- cephalosporanic acids antibacterials

Acetazolamide (225) and methazolamide (226) are two carbonic anhydrase inhibitors which can be derivatized by Mannich-type derivatives to increase their solubility. Under physiological conditions the parent compound is regenerated (71JMC458). Cefazolin (227) is a thiadiazole analog of cephalosporanic acid useful as an antibacterial (70MI42701). 

It has been observed critically that the natural products usually exhibit a relatively lower level of antibacterial activity. Therefore, the articulate and judicial cleavage of the amide bond of the aminoadipyl side-chain present in cephalosporin C provides 7-amino-cephalosporanic acid (7-ACA), which is most ideally suitable for the synthesis of a wide range of semisynthetic cephalosporins via acylation of the C(7)-amino fimctional moiety as depicted under ... 

---