22083-78-9

Basic information

• Product Name: 2-PYRROLIDIN-2-YLPYRIDINE
• Synonyms: Pyridine, 2-(2S)-2-pyrrolidinyl-
• CAS NO: 22083-78-9
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.20498
• Mol File: 22083-78-9.mol

Chemical Properties

• Boiling Point: 60 °C(Press: 0.4 Torr)
• Appearance: /
• Density: 1.042±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.47±0.10(Predicted)
• CAS DataBase Reference: 2-PYRROLIDIN-2-YLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PYRROLIDIN-2-YLPYRIDINE(22083-78-9)
• EPA Substance Registry System: 2-PYRROLIDIN-2-YLPYRIDINE(22083-78-9)

Safety Data

• Hazardous Substances Data: 22083-78-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-PYRROLIDIN-2-YLPYRIDINE is used as a catalyst for the enantioselective addition of diethylzinc to aldehydes. This reaction is crucial in the formation of optically active secondary alcohols, which are essential building blocks in the synthesis of various pharmaceuticals, agrochemicals, and natural products. The application of 2-PYRROLIDIN-2-YLPYRIDINE as a catalyst in this process enables the production of these valuable compounds in high yields with excellent enantioselectivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-PYRROLIDIN-2-YLPYRIDINE is used as a key intermediate in the synthesis of various drug candidates. Its unique structure and reactivity make it an attractive starting material for the development of novel therapeutic agents with potential applications in the treatment of various diseases and medical conditions.
Used in Research and Development:
2-PYRROLIDIN-2-YLPYRIDINE is also employed as a valuable research tool in academic and industrial laboratories. Its use as a catalyst in enantioselective reactions allows chemists to explore new synthetic routes and develop innovative methodologies for the preparation of complex organic molecules. 2-PYRROLIDIN-2-YLPYRIDINE's versatility and utility in catalysis make it an indispensable asset in the field of chemical research and development.

Upstream product

• 133031-58-0 2-<(2S)-1-benzyloxycarbonyl-2-pyrrolidinyl>pyridine 
• 63808-36-6 (2S)-2-cyanopyrrolidine-1-carboxylic acid benzyl ester 
• 131684-98-5 2-pyridine-γ-oxo butanal 
• 100-70-9 2-Cyanopyridine 
• 1380494-92-7 3-(1,3-dioxolan-2-yl)-1-(pyridin-2-yl)propan-1-one 

Downstream Products

• 68582-51-4 2-nicotine 
• 133031-60-4 2-<1-(α-methoxy-α-trifluoromethylphenylacetyl)-2-pyrrolidinyl>pyridine 
• 133031-59-1 2-<(2S)-1-benzyl-2-pyrrolidinyl>pyridine 

Relevant articles and documents

Metal complexes of chiral pyridine ligands. X-ray structure of nitratobispyridine>copper(II) nitrate

Cobalt(II), nickel(II), and copper(II) complexes of 2-pyridine (L) have been synthesized and characterized.The crystal structure of the complex NO3 has been determined by X-ray diffraction.Crystals are monoclinic, space group P2+, with a = 10.766(3), b = 7.525(2), c = 13.447(4) Angstroem, β = 104.64(2) deg, and Z = 2.The structure consists of + cations and NO3- anions.The copper atom has a distorted trigonal bipyramidal coordination geometry with the two pyrrolidine nitrogens and one nitrate oxygen occupying the equatorial positions and the two pyridine nitrogens at the apices.The crystalline cohesion is ensured by a network of hydrogen bonds involving the pyrrolidine groups as donors and both coordinate and uncoordinate nitrates as acceptors.KEY WORDS: Metal complexes, chiral, pyridine, ligands, pyridine derivatives.

Design, synthesis, and evaluation of pyrrolidine based CXCR4 antagonists with in vivo anti-tumor metastatic activity

The chemokine receptor CXCR4 has been proposed as a drug target based on its important functions in HIV infection, inflammation/autoimmune diseases and cancer metastasis. Herein we report the design, synthesis and evaluation of novel CXCR4 antagonists based on a pyrrolidine scaffold. The structural exploration/optimization identified numerous potent CXCR4 antagonists, represented by compound 46, which displayed potent binding affinity to CXCR4 receptor (IC50 = 79 nM competitively displacing fluorescent 12G5 antibody) and inhibited CXCL12 induced cytosolic calcium flux (IC50 = 0.25 nM). Moreover, in a transwell invasion assay, compound 46 significantly mitigated CXCL12/CXCR4 mediated cell migration. Compound 46 exhibited good physicochemical properties (MW 367, logD7.4 1.12, pKa 8.2) and excellent in vitro safety profiles (e.g., hERG patch clamp IC50 > 30 μM and minimal CYP isozyme inhibition). Importantly, 46 displayed much improved metabolic stability in human and rat liver microsomes. Lastly, 46 demonstrated marked efficacy in a cancer metastasis model in mice. These results strongly support 46 as a prototypical lead for the development of promising CXCR4 antagonists as clinical candidates.

HETEROARYL COMPOUNDS AS CXCR4 INHIBITORS, COMPOSITION AND METHOD USING THE SAME

The present disclosure provides heteroaryl compounds of Formula (I), processes for their preparation, pharmaceutical compositions containing them, and their use in the treatment of diseases and disorders, arising from or related to the CXCR4 pathway.

Synthesis of 1-substituted 2-[2S)-2-pyrrolidinyl]pyridine from L-Proline

The synthesis of optically active 2-[(2S)-2-pyrrolidinyl]pyridine from L-proline is reported. This compound can be further alkylated to give the corresponding N-methyl- and N-benzylpyrrolidinyl derivatives.