393509-05-2

Basic information

• Product Name: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
• Synonyms: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
• CAS NO: 393509-05-2
• Molecular Weight: 436.708
• Mol File: 393509-05-2.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid(393509-05-2)
• EPA Substance Registry System: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid(393509-05-2)

Safety Data

• Hazardous Substances Data: 393509-05-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid is used as a potential pharmaceutical intermediate or active pharmaceutical ingredient (API) for drug development. Its carboxylic acid functional group and cyclopenta[b]indol-3-yl core suggest potential activity as an agonist or antagonist at various receptors, such as serotonin receptors. The presence of bromine, chlorine, and fluorine atoms in the molecule may also enhance its pharmacological properties or metabolic stability.
Used in Drug Development Research:
In the field of drug development research, (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid is used as a compound for further research and testing. Its unique structure and functional groups make it a promising candidate for exploring its potential uses and properties in the context of drug development. This may include investigating its interactions with various receptors, its efficacy in treating specific conditions, and its safety profile.
Used in Medicinal Chemistry:
(R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid is utilized in medicinal chemistry as a compound with potential therapeutic applications. Its structural features, including the carboxylic acid group and the presence of halogen atoms, make it an interesting molecule for studying its interactions with biological targets and its potential to be optimized for specific therapeutic purposes.

Upstream product

• 393509-04-1 [5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 371-40-4 4-fluoroaniline 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 
• 393509-24-5 C₁₂H₁₃N*C₂₀H₁₆BrClFNO₂ 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 869194-37-6 (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol 
• 869194-32-1 5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one 
• 869194-30-9 5-bromo-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one 
• 393509-21-2 ethyl (7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 20826-94-2 ethyl (2-oxocyclopentyl)acetate 
• 571170-85-9 (5-bromo-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl)-acetic acid methyl ester 
• 571170-84-8 [2-(2-bromo-4-fluoro-phenylimino)-cyclopentyl]-acetic acid ethyl ester 

Downstream Products

• 1027400-35-6 methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 
• 1026405-15-1 acetic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 
• 1026726-96-4 methanesulfonic acid 5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 
• 1009099-48-2 1-((3S)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)ethane-1,2-diol 
• 1026032-05-2 acetic acid 5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 
• 1009099-50-6 1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone 
• 1009099-49-3 ((3S)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)methanol 
• 571170-77-9 laropiprant 
• 571170-92-8 [4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester 
• 794535-36-7 [5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid 
• 936337-07-4 methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 
• 571170-89-3 [5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester 

Relevant articles and documents

Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4- tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524)

The discovery of the potent and selective prostaglandin D2 (PGD2) receptor (DP) antagonist [(3R)-4-(4-chlorobenzyl)-7-fluoro-5- (methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (13) is presented. Initial lead antagonists 6 and 7 were found to be potent and selective DP antagonists (DP Ki = 2.0 nM for each); however, they both suffered from poor pharmacokinetic profiles, short half-lives and high clearance rates in rats. Rat bile duct cannulation studies revealed that high concentrations of parent drug were present in the biliary fluid (Cmax = 1100 μM for 6 and 3900 μM for 7). This pharmacokinetic liability was circumvented by replacing the 7-methylsulfone substituent present in 6 and 7 with a fluorine atom resulting in antagonists with diminished propensity for biliary excretion and with superior pharmacokinetic profiles. Further optimization led to the discovery of the potent and selective DP antagonist 13.

Method of Treating Pathological Blushing

A method of treating pathological blushing is disclosed wherein the patient is administered a DP receptor antagonist. Compositions containing DP antagonists are also included.

NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT

The present invention encompasses compounds of Formula I: as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating dyslipidemias. Pharmaceutical compositions and methods of use are also included.

METHOD OF TREATING ATHEROSCLEROSIS, DYSLIPIDEMIAS AND RELATED CONDITIONS

A method of treating atherosclerosis, dyslipidemia and related conditions is disclosed wherein a compound of formula I: or a pharmaceutically acceptable salt or solvate thereof is administered to the patient in combination with a DP receptor antagonist. T

NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT

The present invention encompasses compounds of Formula (I); as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating dyslipidemias. Pharmaceutical compositions and methods of use are also included.

On the mechanism of an asymmetric α,β-unsaturated carboxylic acid hydrogenation: Application to the synthesis of a PGD2 receptor antagonist

Ruthenium complexes employing axially chiral ligands were found to be effective asymmetric hydrogenation catalysts for the reduction of α,β-unsaturated ene acid 1-E to give 2, a prostaglandin D2 (PGD2) receptor antagonist. With [(S-B

NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT

The present invention relates to niacin receptor agonists of formula: (I); as well as pharmaceutically acceptable salts and solvates. The compounds are useful for treating dyslipidemias, and in particular, reducing serum LDL, VLDL and triglycerides, and raising HDL levels. Pharmaceutical compositions and methods of treatment are also included.

An efficient enzyme-catalyzed kinetic resolution: Large-scale preparation of an enantiomerically pure indole-ethyl ester derivative, a key component for the synthesis of a prostaglandin D2 receptor antagonist, an anti-allergic rhinitis drug can

Three racemic esters including indole-ethyl ester 1 as well as its related derivatives 3 and 4 in Scheme 1, all synthetic intermediates for the preparation of chiral compound 5, were used as substrates to evaluate the catalytic potentials of a panel of co

Stereoselective formation of carbon-carbon bonds via SN2- displacement: Synthesis of substituted cycloalkyl[b]indoles

A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been accomplished. The key features of this approach are (1) the utilization of a Japp-Klingemann condensation/Fischer cyclization to prepare cycloalkyl[b] indolones, (2) the asymmetric borane reduction of these heterocyclic ketones with (S)-OAB to obtain enantiomerically pure alcohols, and (3) the stereoselective SN2-displacement of these indole alcohol substrates with a carbon nucleophile under Mitsunobu conditions to set the C1 or C3 tertiary carbon stereocenter. The use of trimethylphosphine (PMe3) and bis(2,2,2-trichloroethyl) azodicarboxylate (TCEAD) was found to have an effect on the Mitsunobu dehydrative alkylation.