24016-03-3

Basic information

• Product Name: 2-Amino-3-benzyloxypyridine
• Synonyms: TIMTEC-BB SBB000394;3-(BENZYLOXY)PYRIDIN-2-AMINE;3-Benzyloxy-2-pyridylamine;2-AMINO-3-BENZYLOXYPYRIDINE;3-Benzyloxy-2-aminopyridine;3-Benzyloxy-pyridin-2-ylamine;4-(Benzyloxy)-2-pyridinamine;Pyridine, 2-amino-3-(benzyloxy)-
• CAS NO: 24016-03-3
• Molecular Formula: C₁₂H₁₂N₂O
• Molecular Weight: 200.24
• EINECS: 245-983-9
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Series;Pyridine;Pyridines derivates;Nucleotides and Nucleosides;Pyridines;Bases & Related Reagents;Nucleotides;C9 to C46;Heterocyclic Building Blocks;Amines;Aromatics;Heterocycles;A-AM;Bioactive Small Molecules;Building Blocks;C12;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 24016-03-3.mol

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 337.96°C (rough estimate)
• Flash Point: 172.6 °C
• Appearance: Green to brown/Crystalline Powder
• Density: 1.1131 (rough estimate)
• Vapor Pressure: 2.02E-05mmHg at 25°C
• Refractive Index: 1.6660 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.40±0.10(Predicted)
• BRN: 392674
• CAS DataBase Reference: 2-Amino-3-benzyloxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-benzyloxypyridine(24016-03-3)
• EPA Substance Registry System: 2-Amino-3-benzyloxypyridine(24016-03-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-24/25-36/37/39-22,26-36
• RIDADR: UN2811
• WGK Germany: 3
• Hazardous Substances Data: 24016-03-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-3-benzyloxypyridine is used as a key intermediate in the preparation of pyridinyl/pyridazinyloxymethyl substituted Raf kinase inhibitors. These inhibitors are crucial in the development of targeted therapies for various diseases, including cancer, due to their ability to modulate the activity of Raf kinase.
Additionally, 2-Amino-3-benzyloxypyridine is used in the synthesis of 1-acetyl-2-[2-(3-benzyloxypyridinyl)]iminoimidazolidine, which is another important compound in the pharmaceutical industry. 2-Amino-3-benzyloxypyridine has potential applications in the development of new drugs targeting various diseases.
Furthermore, 2-Amino-3-benzyloxypyridine is utilized in the formation of 9-benzyloxy-3-ethoxycarbonylpyrido[1,2-a]pyrimidin-4-one upon condensation with diethyl ethoxymethylene malonate. 2-Amino-3-benzyloxypyridine serves as a building block for the development of novel therapeutic agents with potential applications in the treatment of various medical conditions.

Biochem/physiol Actions

2-Amino-3-benzyloxypyridine is an inhibitor of mitogen-activated protein kinase p38α activity.

InChI:InChI=1/C12H12N2O/c13-12-11(7-4-8-14-12)15-9-10-5-2-1-3-6-10/h1-8H,9H2,(H2,13,14)/p+1

Upstream product

• 16867-03-1 2-amino-3-hydroxypyridine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 123420-42-8 isopropylidene N-(3-benzyloxy-2-pyridyl) aminomethylenemalonate 
• 143702-66-3 1-Benzyloxy-7-nitro-4a,5,10,11-tetraaza-benzo[b]fluorene 
• 143702-80-1 1-Benzyloxy-8-nitro-4a,5,10,11-tetraaza-benzo[b]fluorene 
• 96428-16-9 8-(phenylmethoxy)imidazo[1,2-a]pyridine 
• 146294-93-1 methyl N-(3-benzyloxy-2-pyridyl)-α-p-nitrophenylglycinate 
• 96428-75-0 5-Benzyloxy-2,3-dihydro-1H-cyclopenta[4,5]imidazo[1,2-a]pyridine 
• 146070-56-6 8-benzyloxy-3-hydroxy-2-p-nitrophenylimidazo<1,2-a>pyridine 
• 151322-74-6 3-(benzyloxy)-2-(butylamino)pyridine 
• 85333-18-2 8-Benzyloxy-2-butyl-imidazo[1,2-a]pyridin-3-ylamine 
• 96428-74-9 2-ethyl-3-methyl-8-phenylmethoxyimidazo[1,2-a]pyridine 
• 137044-53-2 9-hydroxy-pyrido<1,2-a>pyrimidin-5-ium perchlorate 
• 96428-73-8 8-Benzyloxy-3-ethyl-2-methyl-imidazo[1,2-a]pyridine 
• 110223-30-8 8-Benzyloxy-3-methoxy-2-methyl-imidazo[1,2-a]pyridine; hydrobromide 
• 146070-54-4 8-benzyloxy-3-hydroxy-2-phenylimidazo<1,2-a>pyridine 

Relevant articles and documents

Highly Selective, Reversible Inhibitor Identified by Comparative Chemoproteomics Modulates Diacylglycerol Lipase Activity in Neurons

Diacylglycerol lipase (DAGL)-α and -β are enzymes responsible for the biosynthesis of the endocannabinoid 2-arachidonoylglycerol (2-AG). Selective and reversible inhibitors are required to study the function of DAGLs in neuronal cells in an acute and temporal fashion, but they are currently lacking. Here, we describe the identification of a highly selective DAGL inhibitor using structure-guided and a chemoproteomics strategy to characterize the selectivity of the inhibitor in complex proteomes. Key to the success of this approach is the use of comparative and competitive activity-based proteome profiling (ABPP), in which broad-spectrum and tailor-made activity-based probes are combined to report on the inhibition of a protein family in its native environment. Competitive ABPP with broad-spectrum fluorophosphonate-based probes and specific β-lactone-based probes led to the discovery of α-ketoheterocycle LEI105 as a potent, highly selective, and reversible dual DAGL-α/DAGL-β inhibitor. LEI105 did not affect other enzymes involved in endocannabinoid metabolism including abhydrolase domain-containing protein 6, abhydrolase domain-containing protein 12, monoacylglycerol lipase, and fatty acid amide hydrolase and did not display affinity for the cannabinoid CB1 receptor. Targeted lipidomics revealed that LEI105 concentration-dependently reduced 2-AG levels, but not anandamide levels, in Neuro2A cells. We show that cannabinoid CB1-receptor-mediated short-term synaptic plasticity in a mouse hippocampal slice model can be reduced by LEI105. Thus, we have developed a highly selective DAGL inhibitor and provide new pharmacological evidence to support the hypothesis that "on demand biosynthesis" of 2-AG is responsible for retrograde signaling.

Multi-substituted amine compound and its preparation and use (by machine translation)

The invention belongs to the field of medical technology, in particular, the present invention provides the following formula I shown multi-substituted amine compound or its isomer or its pharmaceutically acceptable salt, ester, prodrug or hydrate, its pharmaceutical composition, preparation method thereof and its use in the preparation of medicine for treating aids in use. The compound or pharmaceutical composition containing the compound can be used as an inhibitor for inhibiting HIV integrase with LEDGF/p75 between protein - protein interaction and HIV integrase dimerization, then can be used for the treatment of aids. . (by machine translation)

Preparation method of high-purity paliperidone intermediate

The invention belongs to the technical field of medicine, and particularly discloses a preparation method of a high-purity paliperidone intermediate 3-(2-chloroethyl)-9-hydroxyl-2-methyl-6,7,8,9-tetrahydro-4H-pyridino[1,2-a] pyrimidine-4-ketone. The preparation method particularly comprises the following steps: preparing 9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyridino[1,2-a] pyrimidine-4-ketone by taking 2-amino-3-hydroxypyridine as a starting raw material and through benzyl protection, ring closure of alpha-acetyl-gamma-butyrolactone and chloro-substitution; dissolving the 9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyridino[1,2-a] pyrimidine-4-ketone into an alcohol solvent, adding acid and a palladium-charcoal catalyst, controlling hydrogen pressure, and after the reaction is completed, performing processes of filtering, concentrating, adjusting the pH value, extracting, concentrating and refining to obtain white-like powdered 3-(2-chloroethyl)-9-hydroxyl-2-methyl-6,7,8,9-tetrahydro-4H-pyridino[1,2-a] pyrimidine-4-ketone. The preparation method is short in cycle, the product is white-like, the yield reaches 70 percent or higher, the purity reaches 99 percent or higher, related impurities of chlorine-removed byproducts are avoided, and the preparation method is suitable for industrialized enlarged production.

Discovery of 1-(3-(benzyloxy)pyridin-2-yl)-3-(2-(piperazin-1-yl)ethyl)urea: A new modulator for amyloid beta-induced mitochondrial dysfunction

Herein, we report a new series of aliphatic substituted pyridyl-urea small molecules synthesized as potential modulators for amyloid beta (Aβ) induced mitochondrial dysfunction. Their blocking activities against Aβ-induced mitochondrial permeability transition pore (mPTP) opening were evaluated by JC-1 assay which measures the change of mitochondrial membrane potential (ΔΨm). The inhibitory activity of sixteen compounds against Aβ-induced mPTP opening was superior or almost similar to that of the standard Cyclosporin A (CsA). Among them, 1-(3-(benzyloxy)pyridin-2-yl)-3-(2-(piperazin-1-yl)ethyl)urea (5x) effectively maintained mitochondrial function and cell viabilities on ATP assay, MTT assay, and ROS assay. Using CDocker algorithm, a molecular docking model presented a plausible binding mode for 5x with cyclophilin D (CypD) receptor as a major component of mPTP. Moreover, hERG and BBB-PAMPA assays presented safe cardiotoxicity and high CNS bioavailability profiles for 5x. Taken as a whole, this report presents compound 5x as a new nonpeptidyl mPTP blocker may hold a promise for further development of Alzheimer's disease (AD) therapeutics.

COMPOUND, COMPOSITIONS, AND METHODS

Compounds having activity as LRRK2 inhibitors are disclosed. The compounds are of formula (I) including stereoisomers, tautomers, pharmaceutically acceptable salts and prodrugs thereof. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

Synthesis and evaluation of new pyridyl/pyrazinyl thiourea derivatives: Neuroprotection against amyloid-β-induced toxicity

Herein, we report synthesis and evaluation of new twenty six small molecules against β amyloid (Aβ)-induced opening of mitochondrial permeability transition pore (mPTP) using JC-1 assay which measures the change of mitochondrial membrane potential (ΔΨm). The neuroprotective effect of seventeen compounds against Aβ-induced mPTP opening was superior to that of the standard Cyclosporin A (CsA). Fifteen derivatives eliciting increased green to red fluorescence percentage less than 40.0% were evaluated for their impact on ATP production, cell viability and neuroprotection against Aβ-induced neuronal cell death. Among evaluated compounds, derivatives 9w, 9r and 9k had safe profile regarding ATP production and cell viability. In addition, they exhibited significant neuroprotection (69.3, 51.8 and 48.2% respectively). Molecular modeling study using CDocker algorithm predicted plausible binding modes explaining the elicited mPTP blocking activity. Hence, this study suggests compounds 9w, 9r and 9k as leads for further development of novel therapy to Alzheimer's disease.

Synthesis and in-vitro anti-hepatitis B virus activity of ethyl 6-Bromo-8-hydroxyimidazo[1,2-a]pyridine-3-carboxylates

A series of ethyl 6-bromo-8-hydroxyimidazo[1,2-a]pyridine-3-carboxylate derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in HepG2.2.15 cells. Nearly half of the tested compounds were proved to be highly effective in inhibiting the replication of HBV DNA with IC50 values ranging from 1.3 to 9.1 μM. Among them, 10o and 10s were identified as the most promising compounds.

Synthesis of 8-hydroxyimidazo[1,2-a]pyridine-2-carboxylic acid and its derivatives

Two new imidazo[1,2-a]pyridines, 8-hydroxyimidazo[1,2-a]pyridine-2-carboxylic acid (4) and ethyl 8-hydroxyimidazo[1,2-a]pyridine-2-carboxylate (6) were prepared via cyclization of 2-aminopyfidin-3-ol (1) with bromopyruvic acid (2) and ethyl bromopyruvate (3), respectively. 8-Hydroxyimidazo[1,2-a]- pyridine-2-carboxylic acid (4) was successfully coupled with various amino acid derivatives via its active ester intermediate into the corresponding amides 22-27. O-protected ethyl 8-hydroxyimidazo[1,2-a]pyridine-2-carboxylate 11 was transformed into its hydrazide 13, acyl azide 14, and amide 15 derivatives.

One-pot synthesis of 3-bromoimidazo[1,2-a]pyridine derivatives accompanied by dimethyl sulfoxide oxidation

3-Bromoimidazo[1,2-a]pyridine derivatives have been directly synthesized from reaction of 2-aminopyridine derivative with α-haloketone derivatives in DMSO at room temperature, accompanied by DMSO oxidation. Copyright

3-`(HETERO) ARYLMETHOXY ! PYRIDINES AND THEIR ANALOGUES AS P38 MAP KINASE INHIBITORS

Compounds of the formula (I), wherein: -X=Y- is selected from -CR2=CR3- and -CR2=N-; R1 is selected from H, halo, NRR', NHC(=O)R, NHC(=O)NRR', NH2SO2R, and C(=O)NRR'; R2 and R3 (where present) are independently selected from H, optionally substituted C1-7 alkyl, optionally substituted C5-20 aryl, optionally substituted C3-20 heterocyclyl, halo, amino, amido, hydroxy, ether, thio, thioether, acylamido, ureido and sulfonamino; R4 is an optionally substituted C5-20 aryl or C5-20 heteroaryl group; and R5 is selected from R5’, halo, NHR5’, C(=O)NHR5’, OR5’, SR5’, NHC(=O)R5’, NHC(=O)NHR5’, NHS(=O)R5’, wherein R5’ is H or C1-3 alkyl (optionally substituted by halo, NH2, OH, SH) are disclosed for use in therapy and for treating diseases ameliorated by inhibiting p38 MAP kinase.