313235-19-7

Usage

Molecular weight

345.43 g/mol

Structure

Esomeprazole has an indole ring, a carboxylic acid group, and a phenylmethyl group.

Stereochemistry

Esomeprazole is the S-enantiomer of omeprazole.

Medicinal use

Esomeprazole is used to treat gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome.

Mechanism of action

Esomeprazole is a proton pump inhibitor that decreases the amount of acid produced in the stomach.

Administration

Esomeprazole is administered orally as delayed-release capsules or tablets.

Efficacy

Esomeprazole is more effective at inhibiting acid production than the racemic mixture of omeprazole.

Upstream product

• 100-39-0 benzyl bromide 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 141410-06-2 (S)-indoline-2-carboxylic acid methyl ester 

Downstream Products

• 912807-49-9 2-((S)-1-benzylindolin-2-yl)propan-2-ol 
• 313234-78-5 1-(2S)-2-fluoromethylindolinyl-2-{4-[(4-chlorophenyl)methyl]piperazinyl}ethan-1-one 
• 313235-21-1 [(2S)-2-(Fluoromethyl)]-1-benzylindoline 
• 313235-20-0 [(2S)-1-benzylindolin-2-yl]methan-1-ol 

Relevant academic research and scientific papers

Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions

Two chiral auxiliaries, 2-[(S)-indolin-2-yl]propan-2-ol 1a and (S)-2-(2-methoxypropan-2-yl)indoline 1b, were synthesised from enantiomerically pure (S)-indoline-2-carboxylic acid 3. High diastereoselectivities in alkylations of enolates of the propanoylamides derived from the two auxiliaries are presented. Surprisingly, both auxiliaries induced the same selectivity at the newly created stereogenic centre. The benzyl bromide and n-butyl iodide alkylation reactions showed diastereomeric ratios that were moderate (81:19) to very good (96:4) and with very good yields (86-98%). When LiCl was used as an enolate coordinating agent, in the benzylation of the enolate from propanoylated auxiliary 1a, a very high crude diastereomeric ratio was obtained (99.7:0.3).

Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 2: Asymmetric synthesis and biological evaluation

A series of chiral benzylpiperazinyl-1-(2,3-dihydro-indol-1-yl)ethanone derivatives were prepared and examined for their affinity at dopamine D2 and D4 receptors. Three compounds having D2/D4 affinity ratios approximating that found for the atypical neuroleptic clozapine were further evaluated in behavioral tests of antipsychotic efficacy and motor side effects.

Benzylpiperazinyl-indolinylethanones

Disclosed are benzylpiperazinyl-indolinylethanone compounds which are useful for the treatment and/or prevention of neuropsychological disorders including, but not limited to, schizophrenia, mania, dementia, depression, anxiety, compulsive behavior, substance abuse, Parkinson-like motor disorders and motion disorders related to the use of neuroleptic agents. Pharmaceutical compositions, including packaged pharmaceutical compositions, are further provided. Compounds of the invention are also useful as probes for the localization of GABAAreceptors in tissue samples.