Synthesis, antibacterial and cytotoxic activity evaluation of hydroxyurea derivatives.

5 Synthesis and biological evaluation of a series (N = 16) of cyclic and acyclic hydroxyurea derivatives, including benzotriazole-, isocyanuric acid- and biuret-containing compounds, are disclosed. 1-N-(benzyloxycarbamoyl)benzotriazole was used as a benzyloxyisocyanate donor, a useful intermediate in the preparation of substituted hydroxyurea. Antibacterial activities of synthesized hydroxyurea derivatives were tested on three E. coli strains, i.e., a strain susceptible to antibiotics, a strain resistant to macrolide antibiotics and a strain resistant to aminoglycoside antibiotics. Six compounds (three acyclic and three cyclic hydroxyureas) showed growth inhibition of the tested E. coli strains, with different specificity toward each strain. Results of the cytotoxic activity evaluation revealed that twelve out of sixteen test compounds were cytotoxic to human acute monocytic leukemia THP-1 and/or human acute T cell leukemia Jurkat cell line. 1-(N-hydroxycarbamoyl) benzotriazole () increased the metabolic activity of both cell lines. Two compounds, 1-(N-hydroxycarbamoyl) benzotriazole (5) and N,N',N''-trihydroxybiuret (15), were identified as potential NO donors.

One pot glucose detection by [Fe(III)(biuret-amide)] immobilized on mesoporous silica nanoparticles: an efficient HRP mimic.

An [Fe(III)(biuret-amide)] complex has been immobilized onto mesoporous silica nanoparticles via Cu(I) catalyzed azide-alkyne click chemistry. This hybrid material functions as an efficient peroxidase mimic and was successfully used for the quantitative determination of hydrogen peroxide and glucose via a one-pot colorimetric assay.

5'-Uridyl derivatives of N-glycosyl allophanic acid and biuret.

(2',3'-O-Isopropylidene-5'-uridyl) 4-(2,3,4,6-tetra-O-acetyl-beta-d-glycopyranosyl)allophanates were obtained in the reactions of 2',3'-O-isopropylidene-uridine and O-peracetylated beta-d-gluco-, galacto- and xylopyranosylamines, and OCNCOCl. 2,3,4,6-Tetra-O-acetyl-beta-d-glucopyranosyl isocyanate and N-(2',3'-O-isopropylidene-5'-uridyl)urea gave 1-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)-5-(2',3'-O-isopropylidene-5'-uridyl)biuret. Deprotection of the beta-d-gluco configured allophanate and biuret was carried out by standard methods.

Synthesis of new glycosyl biuret and urea derivatives as potential glycoenzyme inhibitors.

O-peracetylated 1-(beta-D-glucopyranosyl)-5-phenylbiuret was prepared in the reaction of O-peracetylated beta-D-glucopyranosylisocyanate and phenylurea. The reaction of O-peracetylated N-beta-D-glucopyranosylurea with phenylisocyanate furnished the corresponding 1-(beta-D-glucopyranosyl)-3,5-diphenyl- as well as 3-(beta-D-glucopyranosyl)-1,5-diphenyl biurets besides 1-(beta-D-glucopyranosyl)-3-phenylurea. O-Peracetylated 1-(beta-D-glucopyranosyl)-5-(beta-D-glycopyranosyl)biurets were obtained in one-pot reactions of O-peracetylated beta-D-glucopyranosylamine with OCNCOCl followed by a second glycopyranosylamine of beta-D-gluco, beta-D-galacto and beta-D-xylo configurations. O-Acyl protected 1-(beta-D-glucopyranosyl)-3-(beta-D-glycopyranosylcarbonyl)ureas were obtained from the reaction of beta-D-glucopyranosylisocyanate with C-(glycopyranosyl)formamides of beta-D-gluco and beta-D-galacto configurations. The O-acyl protecting groups were removed under acid- or base-catalyzed transesterification conditions, except for the N-acylurea derivatives where the cleavage of the N-acyl groups was faster than deprotection. Some of the new compounds exhibited moderate inhibition against rabbit muscle glycogen phosphorylase b and human salivary alpha-amylase.

Syntheses, antiinflammatory, and analgesic activities of arylbiurets.

A number of arylbiurets were prepared and evaluated as antiinflammatory and analgesic agents by using the carrageenan paw edema and acetic acid stretching tests. Among them, the antiinflammatory activity of 1,3-dimethyl-5-phenylbiuret (7), 1-ethyl-3-methyl-5-phenylbiuret (11), and 1,1,3-trimethyl-5-phenylbiuret (13) were found to be more potent than phenylbutazone. The analgesic activity of 7 and of 5-(4-chlorophenyl)-1,1,3-trimethylphenylbiuret (16) is higher than that of aminopyrine.

Synthesis and biological activity of isodithiobiurets, dithiobiurets, and dithiazoles.

A series of isodithiobiurets, dithiobiurets, and dithiazoles was synthesized and tested for biological activity. Generally, the compounds potentiated the hypnosis induced by pentobarbitone (50 mg/kg ip) in albino mice and exhibited antifungal and insecticidal activity against Fusarium oxysporum and Periplanata americana, respectively. Some compounds showed anticonvulsant and analgesic activity in albino rats.