Preparation and structure-activity relationships of some 6 alpha-substituted penicillins. 1985

G Burton, and M J Basker, and P H Bentley, and D J Best, and R A Dixon, and F P Harrington, and R F Kenyon, and A G Lashford, and A W Taylor

The influence on the antibacterial activity of introducing a 6 alpha-methoxy group into carbenicillin, and various 6 alpha-substituents into sulbenicillin and piperacillin was examined. Further variations of the side chain aryl group were examined in the 6 alpha-methoxy substituted series. This led to the identification of disodium 6 beta-(D,L-2-carboxy-2-thien-3-ylacetamido)-6 alpha-methoxypenicillanate (5b) as a beta-lactamase stable derivative with useful activity against Enterobacteriaceae, and disodium 6 beta-[D-2-(4-aminophenyl)-2-sulfoacetamido]-6 alpha-methoxypenicillanate (6e) with slightly lower activity against the Enterobacteriaceae but more active against Pseudomonas aeruginosa.

UI MeSH Term Description Entries
D010406 Penicillins A group of antibiotics that contain 6-aminopenicillanic acid with a side chain attached to the 6-amino group. The penicillin nucleus is the chief structural requirement for biological activity. The side-chain structure determines many of the antibacterial and pharmacological characteristics. (Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1065) Antibiotics, Penicillin,Penicillin,Penicillin Antibiotics
D011550 Pseudomonas aeruginosa A species of gram-negative, aerobic, rod-shaped bacteria commonly isolated from clinical specimens (wound, burn, and urinary tract infections). It is also found widely distributed in soil and water. P. aeruginosa is a major agent of nosocomial infection. Bacillus aeruginosus,Bacillus pyocyaneus,Bacterium aeruginosum,Bacterium pyocyaneum,Micrococcus pyocyaneus,Pseudomonas polycolor,Pseudomonas pyocyanea
D004755 Enterobacteriaceae A family of gram-negative, facultatively anaerobic, rod-shaped bacteria that do not form endospores. Its organisms are distributed worldwide with some being saprophytes and others being plant and animal parasites. Many species are of considerable economic importance due to their pathogenic effects on agriculture and livestock. Coliform Bacilli,Enterobacteria,Ewingella,Leclercia,Paracolobactrum,Sodalis
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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