554448-74-7

Basic information

• Product Name: (2R)-2,3-dihydro-1H-inden-2-yl({[(phenylmethyl)oxy]carbonyl}amino)ethanoic acid
• Synonyms: (2R)-2,3-dihydro-1H-inden-2-yl({[(phenylmethyl)oxy]carbonyl}amino)ethanoic acid
• CAS NO: 554448-74-7
• Molecular Weight: 325.364
• Mol File: 554448-74-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R)-2,3-dihydro-1H-inden-2-yl({[(phenylmethyl)oxy]carbonyl}amino)ethanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2,3-dihydro-1H-inden-2-yl({[(phenylmethyl)oxy]carbonyl}amino)ethanoic acid(554448-74-7)
• EPA Substance Registry System: (2R)-2,3-dihydro-1H-inden-2-yl({[(phenylmethyl)oxy]carbonyl}amino)ethanoic acid(554448-74-7)

Safety Data

• Hazardous Substances Data: 554448-74-7(Hazardous Substances Data)

Usage

Description

(2R)-2,3-dihydro-1H-inden-2-yl([(phenylmethyl)oxy]carbonylamino)ethanoic acid is a complex organic compound derived from the amino acid alanine, featuring an additional phenylmethyl group and an inden-2-yl moiety attached to the alpha carbon. Its unique structure may confer potential pharmaceutical properties, making it a promising candidate for drug development and research in biochemistry and pharmacology.

Uses

Used in Pharmaceutical Development:
(2R)-2,3-dihydro-1H-inden-2-yl([(phenylmethyl)oxy]carbonylamino)ethanoic acid is used as a potential pharmaceutical compound for its unique structure, which may offer specific binding properties or altered solubility and stability. This makes it a valuable entity for drug discovery and development, particularly in the fields of medicine and chemistry.
Used in Biochemical Research:
As a research tool in biochemistry, (2R)-2,3-dihydro-1H-inden-2-yl([(phenylmethyl)oxy]carbonylamino)ethanoic acid can be utilized to study its interactions with biological systems, providing insights into its potential applications and mechanisms of action.
Used in Drug Delivery Systems:
The phenylmethyl group in (2R)-2,3-dihydro-1H-inden-2-yl([(phenylmethyl)oxy]carbonylamino)ethanoic acid may enhance its potential use in drug delivery systems, improving the compound's delivery, bioavailability, and therapeutic outcomes in various medical applications.

Upstream product

• 16655-90-6 amino(2,3-dihydro-1H-inden-2-yl)ethanoic acid 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 181227-46-3 (2R)-amino(2,3-dihydro-1H-inden-2-yl)ethanoic acid 

Downstream Products

• 1159097-48-9 (3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-1-[(1R)-1-(2,6-dimethyl-3-pyridinyl)-2-(4-morpholinyl)-2-oxoethyl]-6-[(1S)-1-methylpropyl]-2,5-piperazinedione benzenesulfonic acid 
• 1354788-56-9 2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-(2-methylpropyl)-2,5-dioxo-1-piperazinyl]-N-(2-hydroxyphenyl)-2-[6-(methyloxy)-3-pyridinyl]acetamide 
• 1354788-57-0 2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-(2-methylpropyl)-2,5-dioxo-1-piperazinyl]-2-[6-(dimethylamino)-3-pyridinyl]-N-(2-hydroxyphenyl)acetamide 
• 1354788-58-1 2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-(2-methylpropyl)-2,5-dioxo-1-piperazinyl]-N-(2-hydroxyphenyl)-2-(6-methyl-3-pyridinyl)ethanamide 
• 1354788-59-2 2-[(2R,5R)-2-(cyclopropylmethyl)-5-(2,3-dihydro-1H-inden-2-yl)-3,6-dioxo-1-piperazinyl]-N-(2-hydroxyphenyl)-2-(6-methyl-3-pyridinyl)acetamide 
• 1354788-60-5 2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-(2,2-dimethylpropyl)-2,5-dioxo-1-piperazinyl]-N-(2-hydroxyphenyl)-2-(6-methyl-3-pyridinyl)acetamide 
• 1354788-63-8 2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-(1-ethylpropyl)-2,5-dioxo-1-piperazinyl]-N-(2-hydroxyphenyl)-2-(6-methyl-3-pyridinyl)acetamide 
• 1354788-64-9 2-{(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-[(1S)-1-methylpropyl]-2,5-dioxo-1-piperazinyl}-2-(2,5-dimethyl-3-pyridinyl)-N-(2-hydroxyphenyl)acetamide 
• 1354788-65-0 C₃₂H₃₆N₄O₄ 

Relevant articles and documents

Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: Synthesis, pharmacokinetics, and in vivo potency

A six-stage stereoselective synthesis of indanyl-7-(3′-pyridyl)-(3R, 6R,7R)-2,5-diketopiperazines oxytocin antagonists from indene is described. SAR studies involving mono- and disubstitution in the 3′-pyridyl ring and variation of the 3-isobutyl group gave potent compounds (pKi > 9.0) with good aqueous solubility. Evaluation of the pharmacokinetic profile in the rat, dog, and cynomolgus monkey of those derivatives with low cynomolgus monkey and human intrinsic clearance gave 2′,6′-dimethyl-3′- pyridyl R-sec-butyl morpholine amide Epelsiban (69), a highly potent oxytocin antagonist (pKi = 9.9) with >31000-fold selectivity over all three human vasopressin receptors hV1aR, hV2R, and hV1bR, with no significant P450 inhibition. Epelsiban has low levels of intrinsic clearance against the microsomes of four species, good bioavailability (55%) and comparable potency to atosiban in the rat, but is 100-fold more potent than the latter in vitro and was negative in the genotoxicity screens with a satisfactory oral safety profile in female rats.

NOVEL COMPOUNDS

Compounds of formula (I) wherein R1 is 2-indanyl, R2 is 1-methylpropyl, R3 is a group selected from 2, 6-dimethyl-3-pyridyl or 4,6-dimethyl-3-pyridyl, R4 represents methyl and R5 represents hydrogen or methyl or, R4 and R5 together with the nitrogen atom to which they are attached represent morpholino and pharmaceutically acceptable derivatives thereof are described, as are processes for their preparation, pharmaceutical compositions containing them and their use in medicine, particularly their use as oxytocin antagonists.