230618-41-4

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-6-PYRROLIDIN-1-YLPYRIDINE is used as a target compound in drug discovery and development for its potential to exhibit biological activity. Its structure may contribute to the treatment of certain medical conditions, making it an interesting subject for further research in medicinal chemistry.
Further studies are necessary to fully explore the properties and potential uses of 2-BROMO-6-PYRROLIDIN-1-YLPYRIDINE, as its current applications are primarily speculative based on its chemical structure and the known activities of similar compounds.

InChI:InChI=1/C9H11BrN2/c10-8-4-3-5-9(11-8)12-6-1-2-7-12/h3-5H,1-2,6-7H2

Upstream product

• 109-96-6 3-Pyrroline 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 626-05-1 2,6-Dibromopyridine 
• 123-75-1 pyrrolidine 

Downstream Products

• 877201-65-5 2-(3-nitrophenyl)-6-(pyrrolidin-1-yl)pyridine 
• 332134-93-7 2-benzyl-6-(3-pyrroline-1-yl)pyridine 
• 877202-74-9 PSNCBAM-1 

Relevant academic research and scientific papers

Novel Electrophilic and Photoaffinity Covalent Probes for Mapping the Cannabinoid 1 Receptor Allosteric Site(s)

Undesirable side effects associated with orthosteric agonists/antagonists of cannabinoid 1 receptor (CB1R), a tractable target for treating several pathologies affecting humans, have greatly limited their translational potential. Recent discovery of CB1R negative allosteric modulators (NAMs) has renewed interest in CB1R by offering a potentially safer therapeutic avenue. To elucidate the CB1R allosteric binding motif and thereby facilitate rational drug discovery, we report the synthesis and biochemical characterization of first covalent ligands designed to bind irreversibly to the CB1R allosteric site. Either an electrophilic or a photoactivatable group was introduced at key positions of two classical CB1R NAMs: Org27569 (1) and PSNCBAM-1 (2). Among these, 20 (GAT100) emerged as the most potent NAM in functional assays, did not exhibit inverse agonism, and behaved as a robust positive allosteric modulator of binding of orthosteric agonist CP55,940. This novel covalent probe can serve as a useful tool for characterizing CB1R allosteric ligand-binding motifs.

ALLOSTERIC MODULATORS OF THE CANNIBINOID 1 RECEPTOR

The present technology relates to compounds and compositions of Formulas I, II, VII, and VIII, and methods using such compounds. The compounds and compositions described herein may be used in the treatment or prophylaxis of addiction, metabolic syndrome, obesity, and/or a CB1 receptor-medited disorder.

Diarylureas as allosteric modulators of the cannabinoid CB1 receptor: Structure-activity relationship studies on 1-(4-chlorophenyl)-3-{3-[6-(pyrrolidin-1-yl)pyridin-2-yl]phenyl}urea (PSNCBAM-1)

The recent discovery of allosteric modulators of the CB1 receptor including PSNCBAM-1 (4) has generated significant interest in CB1 receptor allosteric modulation. Here in the first SAR study on 4, we have designed and synthesized a series of analogs focusing on modifications at two positions. Pharmacological evaluation in calcium mobilization and binding assays revealed the importance of alkyl substitution at the 2-aminopyridine moiety and electron deficient aromatic groups at the 4-chlorophenyl position for activity at the CB1 receptor, resulting in several analogs with comparable potency to 4. These compounds increased the specific binding of [3H]CP55,940, in agreement with previous reports. Importantly, 4 and two analogs dose-dependently reduced the Emaxof the agonist curve in the CB1 calcium mobilization assays, confirming their negative allosteric modulator characteristics. Given the side effects associated with CB1 receptor orthosteric antagonists, negative allosteric modulators provide an alternative approach to modulate the pharmacologically important CB1 receptor.

Access to 2-Aminopyridines - Compounds of great biological and chemical significance

2-Aminopyridines are key structural cores of bioactive natural products, medicinally important compounds, and organic materials and thus, extremely valuable synthetic targets. The few reported 6-substituted 2-aminopyridines and the lack of flexible, efficient and general applicable methods for their synthesis demonstrates the urgent need of new methods for their preparation. Reactions between 2,6-dibromopyridine and primary or secondary, cyclic or acyclic, and aliphatic or aromatic amines were shown to selectively yield the respective 6-bromopyridine-2-amines in very high yields which were successfully used as substrates for subsequent C-C cross-coupling reactions. The recently introduced dichloro-bis[1-(dicyclohexylphosphanyl)piperidine]palladium (1) was used as catalyst for the cross-coupling of 6-bromopyridine-2-amines with arylboronic acids, diaryl- and dialkylzinc reagents or olefins and hence, is also an excellent C-C cross-coupling catalyst for this type of substrate. Moreover, all the reaction protocols presented were in each of the catalyses uniformly applied. The scope of both the amination and the cross-coupling reactions are well defined and allow one to simply adapt the reaction protocols directly to other amines and/or coupling partners and, thus, provide for the first time a very flexible and generally applicable reaction protocol to get access to 2-aminopyridines.

FUSED PYRAZINE DERIVATIVES AS KINASE INHIBITORS

A series of quinoxaline derivatives, and analogues thereof, which are functionalised further by a substituted phenyl or pyridinyl moiety, being selective inhibitors of PO kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

Role of copper in catalyzing aryl and heteroaryl-nitrogen (or -oxygen) bond formation under ligand-free and solvent-free conditions

Formation of aryl- or heteroaryl-nitrogen (or -oxygen) bonds under ligand and solvent-free conditions are highly selective to the presence of copper. While bromoarenes undergo C-N (or -O) coupling in stoichiometric presence of copper, heteroaryl bromides require only catalytic amounts of copper(I) salts depending on the position of bromo substituents. Such selectivity coupled with ligand and solvent-free protocols appear promising from the viewpoint of ecology and economy and are more attractive as compared to the existing protocols.

ARYL UREA DERIVATIVES

A method of treating a condition associated with the CB-1 receptor, in particular obesity, by administering an effective amount of an aryl urea CB-1 receptor modulating compound to a subject in need of such treatment.

Quinuclidine compounds and drugs containing the same as the active ingredient

The present invention provides an excellent squalene synthesizing enzyme inhibitor. Specifically, it provides a compound (I) represented by the following formula, a salt thereof or a hydrate of them. In which R1 represents (1) hydrogen atom or (2) hydroxyl group; HAr represents an aromatic heterocycle which may be substituted with 1 to 3 groups; Ar represents an optionally substituted aromatic ring; W represents a chain represented by (1) —CH2—CH2— which may be substituted, (2) —CH=CH— which may be substituted, (3) —C≡C—, (4) —NH—CO—, (5) —CO—NH—, (6) —NH—CH2—, (7) —CH2—NH—, (8) —CH2—CO—, (9) —CO—CH2—, (10) —NH—S(O)l—, (11) —S(O)l—NH—, (12) —CH2—S(O)— or (13) —S(O)l—CH2— (l denotes 0, 1 or 2); and X represents a chain represented by (1) a single bond, (2) an optionally substituted C1-6 alkylene chain, (3) an optionally substituted C2-6 alkenylene chain, (4) an optionally substituted C2-6 alkynylene chain, (5) a formula —Q— (wherein Q represents oxygen atom, sulfur atom, CO or N(R2) (wherein R2 represents a C1-6 alkyl group or a C1-6 alkoxy group)), (6) —NH—CO—, (7) —CO—NH—, (8) —NH—CH2—, (9) —CH2—NH—, (10) —CH2—CO—, (11) —CO—CH2—, (12) —NH—S(O)m—, (13) —S(O)m—NH—, (14) —CH2—S(O)m—, (15) —S(O)m—CH2— (wherein m denotes 0, 1 or 2) or (16) —(CH2)n—O— (wherein n denotes an integer from 1 to 6).

Palladium-catalysed amination of halopyridines on a KF-alumina surface

Palladium-catalysed C-N hetero cross-coupling reactions between bromopyridines and amines (both primary and secondary) can be efficiently performed on a KF-alumina (basic) surface, thus negating the use of strong bases such as sodium tert-butoxide. The reaction conditions are optimised with reference to catalytic systems, solvents and the surface.

Studies on the mechanism of action of 2-formyl-4-pyrrolidinopyridine: Isolation and characterization of a reactive intermediate

This paper describes the mechanism of action of 2-formyl-4- pyrrolidinopyridine (FPP, 1a) which is a catalyst for the hydroxyl-directed methanolysis of α-hydroxy esters. This species was initially designed to act as a nucleophilic catalyst; however, we have ruled out a nucleophilic mechanism by examining the activity of 6-substituted-FPP derivatives. These compounds are more hindered in the vicinity of the pyridine nitrogen than FPP itself but are also more active catalysts. Furthermore, the presence of p- nitrophenol, a mild acid, was found to accelerate the catalytic reaction. These results are inconsistent with a nucleophilic catalysis mechanism. We provide evidence that the reaction instead proceeds via dioxolanone intermediate 10. Dioxolanone 10 can be obtained by treating either the p- nitrophenyl ester or the pentafluorophenyl ester of glycolic acid with FPP in chloroform in the absence of methanol. It has been isolated, characterized, and shown to be kinetically competent when subjected to the conditions of the catalytic reaction.