Some 2-(substituted phenyl)oxazolo[4,5-b]pyridines and 2-(substituted phenyl)oxazolo[5,4-b]pyridines have good antiinflammatory and analgesic activity. A few possess activity comparable to phenylbutazone or indomethacin without producing the irritation in the gastrointestinal tract that acidic antiinflammatory compounds cause.
Nucleophilic substitution of certain alkyl bromo‐2(1H)‐pyridones gave some unexpected products where the alkyl group is substituted and the ring bromine is replaced by hydrogen. The expected ring substituted product is also formed, but only as the minor product in most cases. Many reactions are cited with various nucleophiles, and a plausible mechanism is also presented.
A series of antibacterial N-(omega, omega'-(cycloalkyl, bicyclo[2.2.1]heptyl, and alkyl-substituted phenyl)-sec-alkyl]poly(methylene)triamine and -tetramine hydrochloride salts were synthesized in an effort to develop efficient, nonsystemic inhibitors, particularly for Pseudomonas aeruginosa. In the 1,5,9-triazanonane group, 3 of 16 compounds were effective at 8--10 micrograms/mL against pseudomonads. Efficiency appeared more dependent upon lipophilicity of the nitrogen substituent than other characteristics represented by the three types of rings. A parabolic relationship was observed for the entire set between the hydrophobic parameter, pi, of the lipoidal moiety and minimal inhibitory concentration. One of 16 tetramines, 1-[1,5-bis(3,3-dimethyl-2-norbornyl)-3-pentyl]-1,5,9,13-tetraazatridecane tetrahydrochloride (26f), ranked similarly. An additional two compounds in each series were superior to several commercial cationic detergents in the control of the Gram-negative bacteria. None was inhibitory at up to 200 micrograms/mL for Proteus vulgaris.
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