63189-97-9

Usage

Physical State

Yellow crystalline solid

Common Uses

Production of pharmaceuticals and dyes

Functional Groups

Amino group (-NH2)
Nitro group (-NO2)

Versatility

Serves as a versatile building block for various chemical reactions

Biological Properties

Strong antibacterial properties
Strong antifungal properties

Applications

Intermediate in the synthesis of organic compounds
Utilized in research and industrial applications

Upstream product

• 73166-06-0 4-(hydroxymethyl)-2-nitroacetanilide 
• 17012-22-5 methyl 4-acetamidobenzoate 
• 556-08-1 p-(acetylamino)benzoic acid 
• 623-04-1 4-aminobenzenemethanol 
• 943619-80-5 4-(acetylamino)benzyl acetate 
• 55912-20-4 4-chloro-3-nitrobenzyl alcohol 
• 3987-92-6 methyl 4-amino-3-nitrobenzoate 
• 1588-83-6 4-amino-3-nitrobenzoic acid 
• 51818-98-5 4-acetamido-3-nitrobenzaldehyde 
• 6313-39-9 4-acetamido-3-nitro-benzoic acid methyl ester 

Downstream Products

• 496-72-0 4-methyl-1,2-diaminobenzene 
• 63189-98-0 1,2-diamino-4-hydroxymethylbenzene 
• 92807-01-7 5-(hydroxymethyl)-2-mercapto-1H-benzimidazole 
• 1448350-06-8 4-{[(tert-butyldimethylsilyl)oxy]methyl}-2-nitroaniline 
• 1448350-19-3 N-(4-{[(tert-butyldimethylsilyl)oxy]methyl}-2-nitrophenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-12-6 N-(2-amino-4-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-13-7 N-[2-amino-4-(hydroxymethyl)phenyl]-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF FIBROBLAST GROWTH FACTOR RECEPTOR

Disclosed are heterocyclic compounds as inhibitors of FGFR-4 represented by formula (I). Also disclosed is a pharmaceutical composition that includes an inhibitor of FGFR-4. The compounds maybe used to treat diseases mediated with abnormality of FGFR-4 and /or FGF19, such as hepatocellular carcinoma and other forms of cancer.

Discovery of potent, isoform-selective inhibitors of histone deacetylase containing chiral heterocyclic capping groups and a N-(2-aminophenyl)benzamide binding unit

The synthesis of a novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contain a heterocyclic capping group and a N-(2-aminophenyl)benzamide unit that binds in the active site. In vitro assays for the inhibition of HDAC1, HDAC2, HDAC3-NCoR1, and HDAC8 by the N-(2-aminophenyl)benzamide 24a gave respective IC50 values of 930, 85, 12, and 4100 nM, exhibiting class I selectivity and potent inhibition of HDAC3-NCoR1. Both imidazolinone and thiazoline rings are shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl) benzamides previously reported, an example of each ring system at 1 μM causing an increase in histone H3K9 acetylation in the human cell lines Jurkat and HeLa and an increase in cell death consistent with induction of apoptosis. Inhibition of the growth of MCF-7, A549, DU145, and HCT116 cell lines by 24a was observed, with respective IC50 values of 5.4, 5.8, 6.4, and 2.2 mM.

HETEROCYCLIC KINASE INHIBITORS

Compounds having the formula (I) are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

Structure-activity relationship of omeprazole and analogues as Helicobacter pylori urease inhibitors

Helicobacter pylori urease belongs to a family of highly conserved urea- hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K+-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K+- ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pK(a)-value of the pyridine, the pK(a)-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of β- mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 μmol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 μmol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.

Possible Anthelmintic Agents: Syntheses of Methyl 5(6)-Substituted-benzimidazole-2-carbamates

Syntheses of α-phenyl-propionitrile (2), α-phenyl-acrylonitrile (3), methyl 5(6)-hydroxymethylbenzimidazole-2-carbamate (6), β-(2-methoxycarbonylamino)-5(6)-benzi

Antiviral thiazolinyl benzimidazoles

Certain thiazolinyl or thiazinyl ketobenzimidazole compounds and derivatives thereof are useful as antiviral agents.

Carbonyl-substituted 1-sulfonylbenzimidazoles

Certain carbonyl-substituted-1-sulfonylbenzimidazole compounds are useful as antiviral agents.