Abstract
RAPID inactivation of penicillins F, G, K and X in acid solution was demonstrated at an early date1, and was widely assumed to be a general property until 1954, when phenoxymethylpenicillin (penicillin V) was shown to be relatively stable towards mineral acids2. The recent isolation in these Laboratories of 6-aminopenicillanic acid3 permitted the synthesis of many hitherto inaccessible penicillins, including an extended series of acid-stable α-aryloxyalkylpenicillins4 of which one, α-phenoxyethylpenicillin, is now in clinical use. Both penicillin V and its newer homologues are well absorbed from the gastrointestinal tract and hence can be given by mouth, but they show useful antibacterial activity only against Gram-positive bacteria. Benzylpenicillin (penicillin G) has a broader antibacterial spectrum, but is not suitable for oral administration. We therefore prepared a series of α-substituted benzyl penicillins (I) in the hope of finding an acid-stable penicillin active against Gram-negative as well as Gram-positive bacteria.
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