393509-04-1

Basic information

• Product Name: Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-
• CAS NO: 393509-04-1
• Molecular Formula: C20H16BrClFNO2
• Molecular Weight: 436.708
• Mol File: 393509-04-1.mol

Chemical Properties

• CAS DataBase Reference: Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-(393509-04-1)
• EPA Substance Registry System: Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-(393509-04-1)

Safety Data

• Hazardous Substances Data: 393509-04-1(Hazardous Substances Data)

Upstream product

• 923580-07-8 (2E)-[5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-ylidene]acetic acid 
• 393509-22-3 (+/-) 2-(7-fluoro-1,2,3-trihydrocyclopenta[2,3-b]indol-3-yl)acetic acid 
• 393509-23-4 (5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid 
• 571170-84-8 [2-(2-bromo-4-fluoro-phenylimino)-cyclopentyl]-acetic acid ethyl ester 
• 571170-85-9 (5-bromo-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl)-acetic acid methyl ester 
• 622-95-7 4-chlorobenzyl bromide 
• 186581-53-3 diazomethane 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 393509-21-2 ethyl (7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate 
• 371-40-4 4-fluoroaniline 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 20826-94-2 ethyl (2-oxocyclopentyl)acetate 

Downstream Products

• 393509-05-2 [(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 923580-07-8 (2E)-[5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-ylidene]acetic acid 
• 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 
• 936337-07-4 methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 
• 794535-36-7 [5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid 
• 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 
• 571170-77-9 laropiprant 
• 878886-58-9 C₁₂H₁₃N*C₂₀H₁₆BrClFNO₂ 
• 393509-24-5 C₁₂H₁₃N*C₂₀H₁₆BrClFNO₂ 

Relevant articles and documents

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.

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.

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