Acetic acid preparations antibacterial activity

Acetic acid preparations (usually 2-5% solutions) have both antibacterial and antifungal activities. They are particularly useful against P. aeruginosa Staphylococci, p-hemolytic Streptococci, Candida species, and Aspergillus. No organisms are resistant to these... 

Only one cyclic hydroxamic acid which contains the pyrido[2,3-d]-pyrimidine ring system has been reported.This is 2-methyl-3-hydroxypyrido[2,3-d]pyrimidin-4(3i/)-one (21) which was prepared by the action of acetic anhydride on 2-aminonieotinhydroxamic acid (20) or from ethyl 2-aeetamidonicotinate (22) and hydroxylamine. In view of the known antibacterial activity of certain cyclic hydroxamic acids further work on these compounds would be of interest. 

Method E, which assumes the N(7)-C(7a) bond formation in the cyclization step, is also rarely used in the synthesis of thienopyridines. For example, the method (1997H255, 1998JMC(E)33, 1998PS21) for the preparation of 4-oxo-4,7-di-hydrothieno[2,3-Z>]pyridine-5-carboxylic acid esters 54 is based on intramolecular /V-nucleophilic substitution of (E/Z)-aminomethylene derivatives of (2,5-dichloro-3-thenoyl)acetic acid esters 52 in the presence of a strong base. Esters 52 and products of their alkaline hydrolysis 56 have an antibacterial action the influence of the substituents on the biological activity of the resulting compounds was studied. 

The first work in this area was the synthesis of lO-oxa-lO-deazaAMT (IV.52), which was reported as early as 1954 by Fairbum and co-workers [107]. The key building block in this synthesis was the a-ketoaldehyde diethyl acetal, (IV.54), which on reaction with 2,4,5,6-tetraaminopyrimidine at pH 3.0 (90 °C for 2 h) and subsequent vigorous treatment with HCl (100 °C, 15 min) afforded the diester (IV.53) in low yield. Compound (IV.54) was prepared from diethyl V-(4-hydroxybenzoyl)-L-glutamate by reaction with 2,3-epoxy-1,1-diethoxypropane followed by oxidation of the resultant secondary alcohol with chromic acid. Alkaline hydrolysis of (IV.53) yielded (IV.52). The product was assumed to be 6- rather than 7-substituted on the basis that the 5-amino group in 2,4,5,6-tetraaminopyrimidine is the most nucleophilic and therefore most likely to react with the keto group in (IV.54). Antibacterial activity against S. faecium was observed. 

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