74190-66-2

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(4-Methoxy-phenyl)-pyrrolidine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of biologically active compounds.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-(4-Methoxy-phenyl)-pyrrolidine is utilized as a building block to explore its potential in creating new therapeutic agents.
Used in Pain Management:
2-(4-Methoxy-phenyl)-pyrrolidine is used as an analgesic agent for its potential to manage pain, thanks to its inherent pain-relieving properties.
Used in Inflammation Treatment:
In the medical industry, 2-(4-Methoxy-phenyl)-pyrrolidine is considered for its anti-inflammatory properties, making it a candidate for the development of drugs aimed at reducing inflammation.
Used in Drug Development:
2-(4-Methoxy-phenyl)-pyrrolidine is used as a potential therapeutic candidate in drug development due to its interaction with various biological targets, which may lead to the creation of new treatments for different conditions.

InChI:InChI=1/C11H15NO/c1-13-10-6-4-9(5-7-10)11-3-2-8-12-11/h4-7,11-12H,2-3,8H2,1H3/p+1/t11-/m1/s1

Upstream product

• 128100-35-6 5-(4-methoxyphenyl)pyrrolidin-2-one 
• 100-09-4 4-methoxybenzoic acid 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 5724-81-2 1-pyrroline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 52244-70-9 4-(4-methoxyphenyl)butan-1-ol 
• 123-75-1 pyrrolidine 
• 14774-77-7 p-methoxyphenyllithium 
• 22217-80-7 2-(4-methoxyphenyl)-1-pyrroline 
• 727418-56-6 3-(4-methoxy-benzoyl)-1-vinyl-pyrrolidin-2-one 
• 94-30-4 ethyl 4-methoxybenzoate 
• 874-90-8 4-methoxybenzonitrile 
• 937652-78-3 4-amino-4-(4-methoxyphenyl)butan-1-ol 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Identification of the first structurally validated covalent ligands of the small GTPase RAB27A

Rab27A is a small GTPase, which mediates transport and docking of secretory vesicles at the plasma membrane via protein-protein interactions (PPIs) with effector proteins. Rab27A promotes the growth and invasion of multiple cancer types such as breast, lung and pancreatic, by enhancing secretion of chemokines, metalloproteases and exosomes. The significant role of Rab27A in multiple cancer types and the minor role in adults suggest that Rab27A may be a suitable target to disrupt cancer metastasis. Similar to many GTPases, the flat topology of the Rab27A-effector PPI interface and the high affinity for GTP make it a challenging target for inhibition by small molecules. Reported co-crystal structures show that several effectors of Rab27A interact with the Rab27A SF4 pocket ('WF-binding pocket') via a conserved tryptophan-phenylalanine (WF) dipeptide motif. To obtain structural insight into the ligandability of this pocket, a novel construct was designed fusing Rab27A to part of an effector protein (fRab27A), allowing crystallisation of Rab27A in high throughput. The paradigm of KRas covalent inhibitor development highlights the challenge presented by GTPase proteins as targets. However, taking advantage of two cysteine residues, C123 and C188, that flank the WF pocket and are unique to Rab27A and Rab27B among the >60 Rab family proteins, we used the quantitative Irreversible Tethering (qIT) assay to identify the first covalent ligands for native Rab27A. The binding modes of two hits were elucidated by co-crystallisation with fRab27A, exemplifying a platform for identifying suitable lead fragments for future development of competitive inhibitors of the Rab27A-effector interaction interface, corroborating the use of covalent libraries to tackle challenging targets. This journal is

α,α′-C-H Bond Difunctionalization of Unprotected Alicyclic Amines

A simple one-pot procedure enables the sequential, regioselective, and diastereoselective introduction of the same or two different substituents to the α- and α′-positions of unprotected azacycles. Aryl, alkyl, and alkenyl substituents are introduced via their corresponding organolithium compounds. The scope of this transformation includes pyrrolidines, piperidines, azepanes, and piperazines.

O-benzoylhydroxylamines as alkyl nitrene precursors: Synthesis of saturated N-heterocycles from primary amines

We introduce O-benzoylhydroxylamines as competent alkyl nitrene precursors. The combination of readily available, stable substrates and a proficient rhodium catalyst provides a straightforward means for the construction of various pyrrolidine rings from the corresponding primary amines. Preliminary mechanistic investigation suggests that the structure of the nitrene precursor plays a role in determining the nature of the resulting reactive intermediate.

Design, synthesis and biological evaluation of N-hydroxy-aminobenzyloxyarylamide analogues as novel selective κ opioid receptor antagonists

Aminobenzyloxyarylamide derivatives 1a-i and 2a-t were designed and synthesized as novel selective κ opioid receptor (KOR) antagonists. The benzoyl amide moiety of LY2456302 was changed into N-hydroxybenzamide and benzisoxazole-3(2H)-one to investigate whether it could increase the binding affinity or selectivity for KOR. All target compounds were evaluated in radioligand binding assays for opioid receptor binding affinity. These efforts led to the identification of compound 1c (κ Ki = 179.9 nM), which exhibited high affinity for KOR. Moreover, the selectivity of KOR over MOR and DOR increased nearly 2-fold and 7-fold, respectively, compared with (±)LY2456302.

Direct α-C-H bond functionalization of unprotected cyclic amines

Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.

Design, synthesis and biological evaluation of aminobenzyloxyarylamide derivatives as selective κ opioid receptor antagonists

Opioid receptors play an important role in both behavioral and mood functions. Based on the structural modification of LY2456302, a series of aminobenzyloxyarylamide derivatives were designed and synthesized as κ opioid receptor antagonists. The κ opioid receptor binding ability of these compounds were evaluated with opioid receptors binding assays. Compounds 1a-d showed high affinity for κ opioid receptor. Especially for compound 1c, exhibited a significant Kivalue of 15.7?nM for κ opioid receptor binding and a higher selectivity over μ and δ opioid receptors compared to (±)LY2456302. In addition, compound 1c also showed potent κ antagonist activity with κ IC50?=?9.32?nM in [35S]GTP-γ-S functional assay. The potential use of the representative compounds as antidepressants was also investigated. The most potent compound 1c not only exhibited potent antidepressant activity in the mice forced swimming test, but also displayed the effect of anti-anxiety in the elevated plus-maze test.

Synthesis of 2-substituted pyrrolidines from nitriles

A novel and synthetically facile production of 2-substituted pyrrolidines from commercially available nitriles is reported herein. This methodology is operationally simple, and only requires the use of an extraction and a single chromatographic purificati

Hammett correlation of nornicotine analogues in the aqueous aldol reaction: Implications for green organocatalysis

(Chemical Equation Presented) A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with ρ = 1.14 (R2 = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organocatalyst.

(Pyrrolidinyl)phenyl carbamates, compositions and use

Novel (pyrrolidinyl)phenyl carbamates and related compounds, intermediates and processes for the preparation thereof, and methods of relieving memory dysfunction utilizing the carbamates and related compounds, or compositions thereof are disclosed.