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Usage

Uses

Used in Pharmaceutical Research:
(3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid is used as a compound in pharmaceutical research for its potential role in the development of new drugs. Its unique molecular structure, including the tetrahydro-1H-pyrrole ring and the trifluoromethyl group, may offer specific interactions with biological targets, making it a promising candidate for drug discovery.
Used in Chemical Synthesis:
(3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid is used as a building block in the synthesis of other compounds. Its carboxylic acid functional group and chiral center provide opportunities for further chemical modifications and the creation of novel molecules with potential applications in various industries.

Upstream product

• 169750-31-6 (3S,4S)-1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid 
• 217096-03-2 trans-1-benzyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester 
• 152188-51-7 ethyl (+/-)-(3R,4R)-1-benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylate 
• 93102-05-7 N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine 

Relevant academic research and scientific papers

Discovery of 1-{(3R,4R)-3-[({5-Chloro-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)methyl]-4-methoxypyrrolidin-1-yl}prop-2-en-1-one (PF-06459988), a Potent, WT Sparing, Irreversible Inhibitor of T790M-Containing EGFR Mutants

First generation EGFR TKIs (gefitinib, erlotinib) provide significant clinical benefit for NSCLC cancer patients with oncogenic EGFR mutations. Ultimately, these patients' disease progresses, often driven by a second-site mutation in the EGFR kinase domain (T790M). Another liability of the first generation drugs is severe adverse events driven by inhibition of WT EGFR. As such, our goal was to develop a highly potent irreversible inhibitor with the largest selectivity ratio between the drug-resistant double mutants (L858R/T790M, Del/T790M) and WT EGFR. A unique approach to develop covalent inhibitors, optimization of reversible binding affinity, served as a cornerstone of this effort. PF-06459988 was discovered as a novel, third generation irreversible inhibitor, which demonstrates (i) high potency and specificity to the T790M-containing double mutant EGFRs, (ii) minimal intrinsic chemical reactivity of the electrophilic warhead, (iii) greatly reduced proteome reactivity relative to earlier irreversible EGFR inhibitors, and (iv) minimal activity against WT EGFR.

Synthesis and antibacterial activity of novel 7-(3-substituted-3 or 4- trifluoromethyl-1-pyrrolidinyl)-8-methoxyfluoroquinolones

The titled compounds were synthesized and evaluated for in vitro antibacterial activity. The (3R,4S)3-aminomethyl-4-trifluoromethyl derivative (S-34109) was confirmed to be optimal because of its superior activity against quinolone and methicillin-resistant Staphyrococcus aureus and low side effect potential.