In vitro antimicrobial activity of some cyclic hydroxamic acids and related lactams

Abstract

Against Enterobacter aerogenes 13048, Serratia marcescens 13880, Klebsiella pneumoniae 10031, Pseudomonas aeruginosa 10145, Escherichia coli 9723, Lactobacillus casei 7469, Lactobacillus plantarum 8014, Leuconostoc dextranicum 8086, and Streptococcus faecalis 8043, the mean minimal inhibitory concentrations of three cyclic hydroxamic acids, 3-amino-3,4-dihydro-1-hydroxycarbostyril, the 6-chloro analog, and the 7-chloro analog, were 0.6, 0.6, and 0.2 ug/ml, and those of the corresponding lactams, 3-amino-3,4-dihydrocarbostyril, the 6-chloro analog, and the 7-chloro analog, were 60, 60, and 6 ug/ml, respectively. Under the same assay conditions the mean minimal inhibitory concentrations of chloramphenicol and kanamycin were both 2 pug/ml. In addition, the cyclic hydroxamic acids but not the lactams inhibited the growth of Candida albicans at miniimal inhibitory concentrations ranging from 20 to 200 pg/ml, at pH 7, as compared with that of amphotericin B, at 2 pg/ml.

Cyclic hydroxamic acid inhibitors of prostate cancer cell growth: Selectivity and structure activity relationships

“…Cyclic hydroxamic acid analogues of 4 have been reported to exhibit antimicrobial activity, and compound 1, but not 4, was mutagenic to Salmonella typhimurium TA98 and TA100 [10][11][12]. Thus, the growthinhibitory effects of such agents are not unexpected.…”

Bioactive heterocycles containing endocyclic N-hydroxy groups

“…Compounds 71a , 71b and 71c exhibited mean MIC values of 0.6, 0.6 and 0.2 μg/mL, respectively, on this panel of bacteria. In addition, chloro-substituted derivatives 71b and 71c weakly inhibited the growth of Candida albicans , with MICs of 20 μg/mL, and were 10-fold more effective than unsubstituted 71a (MIC = 200 μg/mL), even if they were less potent than the reference compound amphotericin B that exhibited MIC value of 0.6 μg/mL [124]. N -hydroxyquinolinone derivatives 72a-d (Fig.…”

Degradation Studies on Benzoxazinoids. Soil Degradation Dynamics of 2,4-Dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and Its Degradation Products, Phytotoxic Allelochemicals from Gramineae

“…The aromatic substitution patterns on benzohydroxamic acids play also a decisive role in their chemical reactivity, because they affect electron densities at reactive positions C-2 and N-4, provoking different chemical behaviors for both series (54,55). There are also many authors that have compared the effects of methoxylated and nonmethoxylated benzohydroxamic acids toward their bioactivities, finding highly significant differences (56). The higher persistence shown by DIBOA allows us to assign it a more important role in chemical defense mechanisms than DIMBOA in plants that produce large amounts of hydroxamic acids.…”