29180-45-8

Usage

Chemical family

Belongs to the piperidine family

Structure

Consists of a piperidine ring with a methyl group attached at the 2 position and a 4-bromobenzyl group attached at the 1 position

Potential uses

May have uses in pharmaceutical research and development due to its potential pharmacological properties

Safety

Should be handled with care and in accordance with proper safety guidelines, as it can be hazardous if not handled properly.

Upstream product

• 589-15-1 1-bromomethyl-4-bromobenzene 
• 109-05-7 2-Methylpiperidin 

Downstream Products

• 1430810-35-7 1-(4-((2-methylpiperidin-1-yl)methyl)phenyl)pyrrolidin-2-one 
• 774547-41-0 N-(4-bromobenzyl)hexylamine 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships for 1-(4-(piperidin-1- ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3

High expression of the aldo-keto reductase enzyme AKR1C3 in the human prostate and breast has implicated it in the development and progression of leukemias and of prostate and breast cancers. Inhibitors are thus of interest as potential drugs. Most inhibitors of AKR1C3 are carboxylic acids, whose transport into cells is likely dominated by carrier-mediated processes. We describe here a series of (piperidinosulfonamidophenyl)pyrrolidin-2-ones as potent (100 nM) and isoform-selective non-carboxylate inhibitors of AKR1C3. Structure-activity relationships identified the sulfonamide was critical, and a crystal structure showed the 2-pyrrolidinone does not interact directly with residues in the oxyanion hole. Variations in the position, co-planarity or electronic nature of the pyrrolidinone ring severely diminished activity, as did altering the size or polarity of the piperidino ring. There was a broad correlation between the enzyme potencies of the compounds and their effectiveness at inhibiting AKR1C3 activity in cells.

Cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage

Described herein is the development of a borane-catalyzed cine-silylative ring-opening of α-methyl azacycles. This transformation involves four-step cascade processes: (i) exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of the resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of the terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal role in the β-amino elimination step.