137892-92-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-ChloroMethyl-1-Methyl-pyrrolidine is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and treatment options. Its unique structure and reactivity allow for the creation of diverse and complex molecular architectures, which can be tailored to target specific medical conditions.
Used in Agrochemical Production:
In the agrochemical industry, (S)-2-ChloroMethyl-1-Methyl-pyrrolidine serves as an intermediate in the production of pesticides and other chemical products. Its incorporation into these compounds can enhance their effectiveness in protecting crops from pests and diseases, ultimately contributing to increased agricultural productivity.
Used in Research and Development:
Due to its versatile reactivity and potential for creating diverse molecular structures, (S)-2-ChloroMethyl-1-Methyl-pyrrolidine is also utilized in the research and development of new drugs and chemical compounds. Scientists and researchers rely on (S)-2-ChloroMethyl-1-Methyl-pyrrolidine to explore novel chemical pathways and develop innovative solutions to various challenges in the fields of medicine, agriculture, and materials science.
It is crucial to handle (S)-2-ChloroMethyl-1-Methyl-pyrrolidine with care, as it is classified as a hazardous chemical. Proper management and safety measures are essential to minimize risks to human health and the environment.

Upstream product

• 34381-71-0 (S)-2-hydroxymethyl-1-methylpyrrolidine 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 147-85-3 L-proline 

Downstream Products

• 174213-44-6 2(S)-(3-Chlorophenoxymethyl)-1-methylpyrrolidine hydrochloride 
• 174213-53-7 1-methyl-2(S)-(phenoxymethyl)pyrrolidine hydrochloride 

Relevant academic research and scientific papers

Synthesis and α4β2 nicotinic affinity of 2- pyrrolidinylmethoxyimines and prolinal oxime ethers

Homochiral E and Z isomers of N-methylprolinal O-isopropyloxime and (1-methyl-2-pyrrolidinyl)methoxyimines were synthesized as candidate bioisosteres of nicotine and its isoxazolic analogue ABT 418. Two of them, namely (S)-2-isopropylideneaminooxymethyl- and (Z)-(S)-2- ethylideneaminooxymethyl-1-methylpyrrolidine, proved to bind at α4β2 nicotinic acetylcholine receptor with submicromolar affinity and remarkable selectivity over α7 and muscarinic receptors thus supporting the hypothesized bioisosteric relationship between their methyloxyimino group and the aromatic heterocycles of the reference ligands.

Asymmetric addition of organolithium reagents to imines favouring (S)-amines

The proline derived chiral catalyst (5) catalyses the asymmetric addition of organolithium reagents to imines, producing (S)-amines in 37-96% yield and up to 21% enantiomeric excess.

A novel series of IKKβ inhibitors part II: Description of a potent and pharmacologically active series of analogs

A novel series of (E)-1-((2-(1-methyl-1H-imidazol-5-yl) quinolin-4-yl) methylene) thiosemicarbazides was discovered as potent inhibitors of IKKβ. In this Letter we document our efforts at further optimization of this series, culminating in 2 with submicromolar potency in a HWB assay and efficacy in a CIA mouse model.

Minimal structural changes determine full and partial nicotinic receptor agonist activity for nicotine analogues

Neuronal α4β2 nicotinic acetylcholine receptors (nAChRs) are ligand-gated ion channels (LGIC) that have been implicated in nicotine addiction, reward, cognition, pain disorders, anxiety, and depression. Nicotine has been widely used as a template for the synthesis of ligands that prefer α4β2 nAChRs subtypes. The most important therapeutic use for α4β2 nAChRs is as replacement therapy for smoking cessation and withdrawal and the most successful therapeutic ligands are partial agonists. In this case, we use the N-methylpyrrolidine moiety of nicotine to design and synthesize new α4β2 nicotinic derivatives, coupling the pyrrolidine moiety to an aromatic group by introducing an ether-bonded functionality. Meta-substituted phenolic derivatives were used for these goals. Radioligand binding assays were performed on clonal cell lines of hα4β2 nAChR and two electrode voltage-clamp experiments were used for functional assays. Molecular docking was performed in the open state of the nAChR in order to rationalize the agonist activity shown by our compounds.

Rigidified acetylcholine mimics: Conformational requirements for binding to neuronal nicotinic receptors

Rigidified derivatives have been designed and synthesized assuming the g+t conformer of acetylcholine (N-C-C-O=+60°, C-C-O-C=180°) as active conformation for binding to cytisine sensitive neuronal nicotinic receptors. The SAR of the compounds evaluated, along with those of more flexible analogues, support the g+t conformer hypothesis and highlight the stringent steric limitation of this nicotinic receptor sub-type. Compound 3e has low μM affinity for cytisine sensitive nicotinic receptor binding sites while being selective with regard to the α-bungarotoxin sensitive subclass. We also report few compounds with μM affinity for the α-bungarotoxin sensitive subclass.

Benzazepine and benzothiazepine derivatives

Vasodilating activity is exhibited by compounds having the formula STR1 wherein X can be --S--or --CH2 --; and R2 is STR2 depending upon the definition of X.