13400-46-9

Usage

Synthesis

(1H-imidazol-4-yl)methanamine is prepared by adding hydroxylamine hydrochloride to a reaction mixture of 4-imidazolecarboxaldehyde, sodium carbonate and distilled water.Experiment steps：Hydroxylamine hydrochloride (1.27 g, 18.3 mmol) was added to a reaction mixture of 4-imidazolecarboxaldehyde (800 mg, 8.3 mmol), sodium carbonate (445 mg, 4.2mmol) and distilled water (14 ml) and was left to react overnight at room temperature with stirring. The resultant mixture was then concentrated in vacuo to 3 ml and placed in an ice bath for precipitation to occur. Solid formed was collected by filtration, dissolved and recrystallized in ethanol to afford the colourless powder oxime, 1H-imidazole-4-carbaldehyde oxime (330 mg). Acetyl chloride (1.06 ml) was added dropwise into methanol (39 ml) in a round bottom flask at 0 °C under nitrogen purge and left to stir for 30 minutes. The oxime was then added into the reaction mixture followed by addition of palladium on carbon, 5% (296 mg, 2.40 mmol). The reaction mixture was hydrogenated at atmospheric pressure overnight. The resultant mixture was then filtered through celite pad, washed with methanol (30 ml) where the filtrate was then collected and concentrated in vacuo to give (1H-imidazol-4-yl)methanamine as a colourless powder (274 mg, 34%).

InChI:InChI=1/C4H7N3/c5-1-4-2-6-3-7-4/h2-3H,1,5H2,(H,6,7)

Upstream product

• 57090-88-7 1H-imidazole-4-carbonitrile 
• 955132-71-5 4?(azidomethyl)?1H?imidazole 

Downstream Products

• 777062-45-0 allyl {[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-[2-(3-chloro-4-{2-[(1H-imidazol-5-ylmethyl)amino]-2-oxoethyl}phenyl)-2-oxoethyl]-4-oxoazetidin-1-yl]}(triphenylphosphoranilidene)acetate 

Relevant academic research and scientific papers

CANCER TREATMENTS TARGETING CANCER STEM CELLS

Disclosed are compounds, methods, compositions, and kits that allow for treating cancer by, e.g., targeting cancer stem cells. In some embodiments, the cancer is colorectal cancer, gastric cancer, gastrointestinal stromal tumor, ovarian cancer, lung cancer, breast cancer, pancreatic cancer, prostate cancer, testicular cancer, or lymphoma. In some embodiments, the cancer is liver cancer, endometrial cancer, leukemia, or multiple myeloma. The compounds utilized in the disclosure are of Formula (0), (O'), and (I):

SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF

Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.

FACTOR XA INHIBITORS

The present invention is directed to compounds of formula (I) and pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of Factor Xa. The present invention is also directed to intermediates used in making such compounds, pharmaceutical compositions containing such a compound, methods to prevent or treat a number of conditions characterized by undesired thrombosis and methods of inhibiting the coagulation of a blood sample.

Pharmaceutically active compounds

Compounds of the formula pharmaceutically acceptable acid addition, basic addition salts or quaternary amine salts thereof, wherein Z is phenyl, substituted phenyl, wherein the substituents are independently one or more of halogen, lower alkylthio, loweralkylsulfonyl, lower alkoxy, oxazol-2-yl; imidazo-1-yl; lower alkyl substituted imidazo-1-yl; or tert-butyl; X is a bond, STR1 Q is lower alkane-diyl or 5, 6, or 7 carbon atoms optionally substituted by --OH; loweralkylnediyl of 6-8 carbon atoms; methylcyclohexylmethyl; tetrahydrofurandiyl; or (C1 -C2) lower alkane-diyl tetrahydrofurandiyl-C1 -C2 loweralkanediyl; wherein the tetrahydrofuran ring is substituted by 0-2 hydroxy groups; Y is a bond; and W is benzimidazol-1-yl or benzimidazol-2-yl are described. These compounds have antiviral activity, antiinflammatory activity and are PAF inhibitors.

Pharmaceutically active compounds

The disclosed invention is compounds represented by the formula and pharmaceutically acceptable acid addition salts and quarternary amine salts thereof, wherein Z is phenyl, naphthyl or adamantyl; substituted phenyl wherein the substituents are one or more of halogen, lower alkoxy, phenoxy, nitrile, nitro, phenylsulfonyl, methylsulfonyl, isoxazol-2-yl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, lower alkyl, loweralkylthio, phenyl, phenylaminothiocarbonyl, or lower alkylaminothiocarbonyl; 5 or 6 membered unsubstituted or substituted heterocyclic ring containing at least one nitrogen and one carbon in the ring, wherein the substituents are one or more of carboxyl, hydroxymethyl, loweralkyl, loweralkylcarbonyl or aryl lower alkyl; or tertiary butyl; X and Y are each independently a bond, -O-, STR1 Q is a divalent substituted or unsubstituted straight or branched chain lower alkanediyl, -lower alkanedinyl- cycloalkanediyl- lower alkanediyl-, lower alkendiyl, lower alkynediyl, phenylene, tetrahydrofurandiyl or tetrahydropyrandiyl; W is a monovalent substituted or unsubstituted aromatic heterocyclic single or fused ring containing from 5 to 10 ring atoms, at least one hetero atom of which is a nitrogen atom, wherein the substituents are hydroxy, amino, carbamoyl, carboxyl, nitrile, nitro, oxo, lower alkoxy carbonyl, halogen, sulfamyl, lower alkyl, lower alkylthio, lower alkoxy, hydroxyloweralkyl, lower alkoxycarbonylloweralkyl, amino loweralkyl, carboxyloweralkyl, guanidino, thioureido, lower alkylsulfonylamino, aminocarbonylloweralkyl, allyloxycarbonylmethyl or carbamoyloxylowralkyl; and W' is divalent W. The compounds have antiviral activity, antiinflammatory activity and are PAF inhibitors.