Semisynthetic .Beta.-lactam antibiotics. Ii. Effect on antibacterial activity of ureido N-substituents in the 6- ( (R) -2- (3- (3,4-dihydroxybenzoyl) -1-ureido) -2-phenylacetamido) penicillanic acids

Ohi, N.; Aoki, B.; Moro, K.; Kuroki, T.; Sugimura, N.; Noto, T.; Nehashi, T.; Matsumoto, M.; Okazaki, H.; Matsunaga, I.

The Journal of Antibiotics 39(2): 242-250


DOI: 10.7164/antibiotics.39.242
Accession: 068516219

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The synthesis and the relationship between in vitro and in vivo activities of 6-[(R)-2-[3-(3,4-dihydroxybenzoyl)-3-R1-1-ureido]-2- phenylacetamido]penicillanic acids having C2 approximately 8 alkyl or substituted alkyl groups as the substituents (R1) are described. In this series, 6-[(R)-2-[3-(3,4-dihydroxybenzoyl)-3-(3-hydroxypropyl)-1-ureido] -2-phenylacetamido]penicillanic acid (1b, AO-1100) showed the most potent protective effect on mice in experimental Pseudomonas aeruginosa infections, although it did not have the strongest in vitro activity among the penicillins we synthesized.