69245-79-0

Upstream product

• 6050-58-4 4-morpholin-4-yl-butan-2-one 
• 34461-00-2 nitromalondialdehyde sodium salt 
• 100-02-7 4-nitro-phenol 
• 110-91-8 morpholine 
• 50-00-0 formaldehyd 

Downstream Products

• 76226-59-0 4-amino-2-morpholinomethylphenol 
• 109-77-3 malononitrile 

Relevant academic research and scientific papers

Cathepsin B inhibitors: Further exploration of the nitroxoline core

Human cathepsin B is a cysteine protease with many house-keeping functions, such as intracellular proteolysis within lysosomes. Its increased activity and expression have been strongly associated with many pathological processes, including cancers. We present here the design and synthesis of novel derivatives of nitroxoline as inhibitors of cathepsin B. These were prepared either by omitting the pyridine part, or by modifying positions 2, 7, and 8 of nitroxoline. All compounds were evaluated for their ability to inhibit endopeptidase and exopeptidase activities of cathepsin B. For the most promising inhibitors, the ability to reduce extracellular and intracellular collagen IV degradation was determined, followed by their evaluation in cell-based in vitro models of tumor invasion. The presented data show that we have further defined the structural requirements for cathepsin B inhibition by nitroxoline derivatives and provided additional knowledge that could lead to non-peptidic compounds with usefulness against tumor progression.

Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols

A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2-Csp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical coupling mechanism involving a six-membered transition state is proposed to rationalize the high levels of ortho-selectivity in the reaction. This protocol provides straightforward access to ortho-aminomethyl-substituted phenols, unnatural amino acids and other bioactive small molecules.

Pyrazole compounds

Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

Cyclocondensation of nitromalonaldehyde sodium salt with substituted 1-amino-3-butanones

Cyclocondensation of nitromalonaldehyde sodium salt with substituted 1-amino-3-butanones afforded 2-dimethyl-, diethylaminomethyl-4-nitrophenols and 2-piperidylo-, morpholylomethyl-4-nitrophenols.

Synthesis of phenols and naphthol with n-morpholinomethyl pendants and their dimethylgallium complexes: Crystal structure of dimethylgallium-[4-nitro-2-(n-morpholinomethyl)-1-phenoxide]

The one-pot Mannich reaction was used to synthesize 2-(n-morpholinomethyl)-1-phenol (1a), 4-methyl-2-(n-morpholinomethyl)-1-phenol (1b), 4-chloro-2-(n-morpholinomethyl)-1-phenol (1c), 4-nitro-2-(n-morpholinomethyl)-1-phenol (1d), and 1-(n-morpholinomethyl)-naphthol (1e). The dimethylgallium complexes of these compounds have been prepared, and compound 2d has been determined by X-ray crystallography. The complex 2d crystallized with one unit having two identical molecules which have intermolecular contacts between the two phenyls caused by face to face π-π stacking. The Ga-O bond distances are noticeably shorter than in the other dimethylgallium phenoxides reported.