13230-21-2

Usage

InChI:InChI=1/C6H7N3O4/c1-13-6(10)3-8-2-5(7-4-8)9(11)12/h2,4H,3H2,1H3

Upstream product

• 5680-79-5 glycine ethyl ester hydrochloride 
• 19182-81-1 1,4-dinitro-1H-imidazole 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 96-34-4 methyl chloroacetate 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 688041-31-8 (4-amino-imidazol-1-yl)-acetic acid methyl ester 
• 930100-40-6 C₁₉H₂₂F₂N₄O₄ 
• 930100-32-6 C₁₈H₂₂F₂N₄O₃ 
• 1309885-13-9 C₂₂H₂₉F₂N₅O₂ 
• 5006-69-9 2-(4-nitro-1H-imidazol-1-yl)ethanol 
• 1153126-46-5 N-(2-hydroxyethyl)-2-(4-nitro-1H-imidazol-1-yl)acetamide 

Relevant academic research and scientific papers

Synthesis and fluorescent characteristics of imidazole-indocyanine green conjugates

We have successfully synthesized imidazole-dye conjugates by linking imidazole and nitroimidazoleacetic acids to an indocyanine green (ICG) carboxylic acid derivative, using an ethanolamine linker. These dye-conjugates show absorbance peaks at 754-756 nm and fluorescence peaks at 780 nm. The dye-conjugates show a blue shift of 25 nm and 30 nm in the absorption and fluorescence spectra respectively when compared to that of standard cardiogreen. There is no change in absorption and fluorescence spectral profiles between the ICG derivative and imidazole conjugates. The extinction coefficients of new ICG derivative and imidazole conjugates are 1.8 times higher than that of standard ICG. The relative quantum yields of the new compounds are 4.5-5.5 times higher than that of the Sigma-Aldrich's ICG. The dyes are tested for hypoxia in-vitro with 4T1 luc cell lines and it is found that the cells treated with 2-nitroimidazole ICG show a contrast of fluorescence signal of 2.5-3.0 for the cells under hypoxic to that of cells under normoxic. However pure ICG shows no significant difference between hypoxic and normoxic cells.

Diamide amino-imidazoles: A novel series of γ-secretase inhibitors for the treatment of Alzheimers disease

The synthesis and structure-activity relationship (SAR) of a novel series of di-substituted imidazoles, derived from modification of DAPT, are described. Subsequent optimization led to identification of a highly potent series of inhibitors that contain a β-amine in the imidazole side-chain resulting in a robust in vivo reduction of plasma and brain Aβ in guinea pigs. The therapeutic index between Aβ reductions and changes in B-cell populations were studied for compound 10h.

IMIDAZOLE COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS

The present invention relates to compounds of the Formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and A are as defined. Compounds of the Formula (I) have activity inhibiting produ

Design and synthesis of heterocyclic hydroxamic acid derivatives as inhibitors of Helicobacter pylori urease

Helicobacter pylori produces ammonia to help counter the acidic environment in the human stomach. The production of ammonia, essential for the microorganism's survival and virulence, is the product of enzymatic conversion of urea by the H. pylori's urease. Inhibition of urease activity by dipeptide hydroxamic acids has previously been demonstrated using a variety of fluorides, thiols and hydroxamic acids. Studies employing computer-aided drug design techniques have been utilized to suggest a novel series of heterocyclic hydroxamic acid derivatives as potential as urease inhibitors. The heterocyclic compounds 7a,b, 10b, 12b, 16b, and 19b have been designed, synthesized, and preliminarily tested as dipeptide mimics which offer a structure that is more biologically stable than that of the reported dipeptide inhibitors.

New antimetastatic hypoxic cell radiosensitizers: Design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues

We designed, based on the molecular orbital (MO) calculation, synthesized, and evaluated the biological activities of the new antimetastatic hypoxic cell radiosensitizer, 2-nitroimidazole-acetamide, TX-1877, and its analogues. Each analogue has an electron-affinic imidazole group, an acetamide group and a certain hydrophilic group to control its biological effect, toxicity, and pharmacokinetics. In in vitro radiosensitization assay, most TX-1877 analogues, which have an electron affinity (EA) of more than 0.9 eV and partition coefficient (P) of more than 0.021, showed satisfactory enhancement ratios (ER > 1.60) at doses of 1 mM. On the other hand, imidazole analogues, such as TX-1908 (EA = 0.67 eV), TX-1910 (EA = -0.34 eV) and TX-1931 (EA = -0.37 eV), which have low electron affinities, had an ER of 1.31 or less. TX-1877 and KIN-806 effectively inhibited tumor regrowth when administered with irradiation in vivo at a dose of 0.4 mg/g. Tumor lung metastasis was inhibited by treatment with either TX-1877 or KIN-806 without irradiation at a dose of 0.4 mg/g. TX-1877 reduced markedly the mean number of metastatic lung nodules in comparison with KIN-806. Moreover, TX-1877 and KIN-806 enhanced macrophage and helper T lymphocyte infiltration for 3 weeks after drug treatment. TX-1877 shows a high EA value and has the C2 of HOMO localizing on N-methylamide and the C2 of LUMO localizing on 2-nitroimidazole group. The MO data might be useful for designing a bifunctional hypoxic cell radiosensitizer. TX-1877 and its analogues are potential antimetastatic hypoxic cell radiosensitizers, which would improve the efficiency of radiotherapy and quality of life in cancer treatment.

Nitroimidazoles, XIV: Synthesis of 4-nitroimidazoles with 1-substituents containing acid, ester or phenol functions, and radiosensitizing efficiency of some of these compounds.

1,4-Dinitroimidazole and 1,4-dinitro-2-methylimidazole were reacted with aminocarboxylic acids and their esters, aminosulfonic acids, and aminophenol to obtain the corresponding 1-substituted-4-nitroimidazoles. The radiosensitizing efficiency of some este