32282-07-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(Benzylamino)-3-aminopyridine is used as a key intermediate in the synthesis of various pharmaceuticals for its reactivity and the presence of versatile functional groups that facilitate the creation of diverse medicinal compounds.
Used in Organic Chemistry:
In the field of organic chemistry, 2-(Benzylamino)-3-aminopyridine is utilized as a building block for the production of other organic chemicals, contributing to the development of new materials and compounds with specific properties.
Used in Therapeutic Agent Development:
2-(Benzylamino)-3-aminopyridine is studied for its potential as a therapeutic agent, particularly in the treatment of diseases such as cancer and neurological disorders, due to its unique chemical structure and reactivity.
Used in Dye Production:
2-(Benzylamino)-3-aminopyridine may also be employed as an intermediate in the production of dyes, where its chemical properties contribute to the creation of dyes with specific color characteristics and applications.

InChI:InChI=1/C12H13N3/c13-11-7-4-8-14-12(11)15-9-10-5-2-1-3-6-10/h1-8H,9,13H2,(H,14,15)

Upstream product

• 452-58-4 2,3-Diaminopyridine 
• 100-52-7 benzaldehyde 
• 100-46-9 benzylamine 
• 99314-92-8 N²-amino-N³-benzyloxycarbonylaminopyridine 
• 99314-94-0 (2-Benzoylamino-pyridin-3-yl)-carbamic acid benzyl ester 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 140-75-0 para-fluorobenzylamine 
• 39856-58-1 3-amino-2-bromopyridine 
• 3723-70-4 benzyl-(3-nitro-pyridin-2-yl)-amine 
• 69634-21-5 N-(3-aminopyridin-2-yl)benzamide 

Downstream Products

• 1350571-52-6 3-benzyl-2-(methylthio)-3H-imidazo[4,5-b]pyridine 
• 1415509-02-2 3-benzyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine 
• 1415509-11-3 C₁₉H₁₆N₄ 
• 61532-31-8 3-benzylimidazo[4,5-b]pyridine-2-thione 
• 61532-32-9 3-(Phenylmethyl)-3H-imidazo<4,5-b>pyridine 
• 41010-46-2 1,3-Dihydro-3-(phenylmethyl)-2H-imidazo<4,5-b>pyridin-2-one 
• 1373397-35-3 3-benzyl-3H-[1,2,3]triazolo[4,5-b]pyridine 
• 250342-75-7 3-benzyl-2-(4'-methoxy-biphenyl-4-yl)-3H-imidazo[4,5-b]pyridine 
• 1016-93-9 2-phenyl-1H-imidazo<4,5-b>pyridine 
• 57806-33-4 3-benzyl-2-methylimidazolo-<4,5-b>-pyridine 

Relevant academic research and scientific papers

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903

The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.

1,2,3-Triazole fused with pyridine/pyrimidine as new template for antimicrobial agents: Regioselective synthesis and identification of potent N-heteroarenes

The 1,2,3-triazole ring fused with pyridine/pyrimidine was explored as new template for the identification of potential antimicrobial agents. The regioselective synthesis of these pre-designed N-heteroarenes was achieved via exploring the application of Buchwald's strategy (i.e. C–N bond formation/reduction/diazotization/cyclization sequence) to the N-heteroarene system. Two of them showed promising antibacterial (comparable to streptomycin) and several showed potent antifungal (comparable to mancozeb) activities.

Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues

In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.

AUTOTAXIN INHIBITORY COMPOUNDS

The present invention relates to compounds of formula I, wherein A1, A2, A3, R1, R2, R3, R4, R5, R6, L, Ar and Q are each as defined herein. The compounds of the present invention are inhibitors of autotaxin (ATX) enzyme activity. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions (e.g. fibrosis) in which ATX activity is implicated.

Rapid construction of imidazopyridines from ortho-haloaminopyridines

A practical strategy for the preparation of imidazopyridine derivatives from ortho-haloaminopyridines utilizing a two-step C-N coupling/cyclization reaction sequence has been developed. This procedure provides rapid and efficient access to many medicinally interesting imidazopyridine compounds and related imidazopyrazine/purine heterocycles.

Synthesis and potent cytotoxicity of some novel imidazopyridine derivatives against MCF-7 human breast adenocarcinoma cell line

[Figure not available: see fulltext.] A series of novel 2-phenyl-3H-imidazo[4,5-b]pyridines and 2-phenyl-3H-imidazo[4,5-c]pyridines and their precursors were synthesized. Their in vitro cytotoxicity against MCF-7 human breast adenocarcinoma cell line has been investigated, and some of the tested compounds have shown high cytotoxic activity against MCF-7 cells. N-Hydroxy-4-(3H-imidazo[4,5-b]pyridin-2-yl)benzenecarboximidamide was the most active compound with IC50 equal to 0.082 μM, which is an activity almost as high as that of a commonly used anticancer drugs docetaxel and imatinib mesylate.

Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles

Upon irradiation, cyclic imines containing o-amido groups are shown to produce reactive intermediates, amino azaxylylenes, which undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex N,O-heterocycles having an additional spiro-connected nitrogen heterocyclic moiety. Modular assembly of the photoprecursors allows expeditious increase of the complexity of the target poly-heterocyclic scaffolds with a minimal number of experimentally simple reaction steps. The photocyclization and subsequent postphotochemical transformations are accompanied by an increase of Lovering's fsp3 factor, thus producing unprecedented three-dimensional molecular architectures, and offering extended sampling of chemical space. Rings in three dimensions: Cyclic imines containing an o-amido group undergo excited-state intramolecular proton transfer to generate amino azaxylylenes. The amino azaxylylenes undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex heterocyclic three-dimensional molecular architectures.

Synthesis and biological evaluation of imidazo[4,5-b]pyridine and 4-heteroaryl-pyrimidine derivatives as anti-cancer agents

A series of N-phenyl-imidazo[4,5-b]pyridin-2-amines, 4-indazolyl-N- phenylpyrimidin-2-amines and N-phenyl-4-pyrazolo[3,4-b]pyridin-pyrimidin-2- amines have been synthesized. Their anti-proliferative activities were tested in HCT-116 human colon carcinoma and MCF-7 breast carcinoma cell lines. Many exhibited potent anti-proliferative and CDK9 inhibitory activities. A lead compound 18b demonstrated the ability to reduce the level of Mcl-1 anti-apoptotic protein, to activate caspase 3/7 and induce cancer cell apoptosis.

Imidazopyridines: A novel class of hNav1.7 channel blockers

A series of imidazopyridines were evaluated as potential sodium channel blockers for the treatment of neuropathic pain. Several members were identified with good hNav1.7 potency and excellent rat pharmacokinetic profiles. Compound 4 had good efficacy (52% and 41% reversal of allodynia at 2 and 4 h post-dose, respectively) in the Chung rat spinal nerve ligation (SNL) model of neuropathic pain when dosed orally at 10 mg/kg.