1039826-29-3

Usage

Uses

Used in Organic Synthesis:
(R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate is used as a building block for the construction of various bioactive molecules and pharmaceutical compounds. Its unique structure and functional groups make it a versatile component in the synthesis of complex organic molecules.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
(R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate is used as a chiral auxiliary in asymmetric synthesis to control the stereochemistry of reactions, leading to the formation of enantiomerically pure products. This is crucial in the development of new drugs and materials where stereochemistry plays a key role in biological activity and selectivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate is used as a key intermediate in the synthesis of chiral drugs. Its specific (R)-configuration allows for the production of drugs with desired biological activities and reduced side effects, contributing to the development of more effective and safer medications.
Used in Material Science:
(R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate is also used in material science for the development of new materials with specific properties. Its unique structure and functional groups can be incorporated into polymers, coatings, and other materials to impart desired characteristics such as chirality, bioactivity, or specific interactions with biological systems.

Upstream product

• 132482-10-1 (R)-1-<(1,1-dimethylethoxy)carbonyl>-2-pyrrolidinemethanolmethanesulfonate 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 

Relevant academic research and scientific papers

Discovery of (R)-5-(benzo[d][1,3]dioxol-5-yl)-7-((1-(vinylsulfonyl)pyrrolidin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (B6) as a potent Bmx inhibitor for the treatment of NSCLC

Described as a Btk inhibitor, ibrutinib also potently inhibits Bmx and EGFR, two good targets for lung cancer. Owing to its high CLogP (4.07) and low aqueous solubility (a potent anti-cancer agent B6, with beneficial physicochemical parameters (CLogP = 2.56, solubility in water ≈ 0.1 mg/ml) meeting the principles of oral drugs. B6 exhibited anti-proliferation activities against EGFR-expressing cells, especially the mutant ones, such as H1975 (L858R/T790M, IC50 = 0.92 ± 0.19 μM) and HCC827 (Del119 IC50 = 0.014 ± 0.01 μM). Moreover, B6 significantly slowed down H1975 tumor growth with anti-tumor rate of 73.9% (p 50 = 35.7 ± 0.1 nM) over other kinases. So, as a potent Bmx inhibitor, B6 has the potential to be an efficacious treatment for NSCLC with acquired drug resistance.

Trisubstituted Pyridinylimidazoles as Potent Inhibitors of the Clinically Resistant L858R/T790M/C797S EGFR Mutant: Targeting of Both Hydrophobic Regions and the Phosphate Binding Site

Inhibition of the epidermal growth factor receptor represents one of the most promising strategies in the treatment of lung cancer. Acquired resistance compromises the clinical efficacy of EGFR inhibitors during long-term treatment. The recently discovered EGFR-C797S mutation causes resistance against third-generation EGFR inhibitors. Here we present a rational approach based on extending the inhibition profile of a p38 MAP kinase inhibitor toward mutant EGFR inhibition. We used a privileged scaffold with proven cellular potency as well as in vivo efficacy and low toxicity. Guided by molecular modeling, we synthesized and studied the structure-activity relationship of 40 compounds against clinically relevant EGFR mutants. We successfully improved the cellular EGFR inhibition down to the low nanomolar range with covalently binding inhibitors against a gefitinib resistant T790M mutant cell line. We identified additional noncovalent interactions, which allowed us to develop metabolically stable inhibitors with high activities against the osimertinib resistant L858R/T790M/C797S mutant.

5-PYRIDINONE SUBSTITUTED INDAZOLES

Various 5-substituted 1-substituted indazoles are described, as are pharmaceutical compositions containing these compounds and methods of treatment of diseases using these compounds. Other embodiments are also described.