393509-13-2

Basic information

• Product Name: methyl [5-acetyl-4-(4-chlorobenzyl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate
• Synonyms: methyl [5-acetyl-4-(4-chlorobenzyl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate
• CAS NO: 393509-13-2
• Molecular Weight: 473.977
• Mol File: 393509-13-2.mol

Chemical Properties

• CAS DataBase Reference: methyl [5-acetyl-4-(4-chlorobenzyl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl [5-acetyl-4-(4-chlorobenzyl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate(393509-13-2)
• EPA Substance Registry System: methyl [5-acetyl-4-(4-chlorobenzyl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate(393509-13-2)

Safety Data

• Hazardous Substances Data: 393509-13-2(Hazardous Substances Data)

Upstream product

• 393509-12-1 methyl [5-bromo-4-(4-chlorobenzyl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 625820-67-9 (3a,5,8b-tribromo-7-methanesulfonyl-1,2,3,3a,4,8b-hexahydro-cyclopenta[b]indol-3-yl)-acetic acid 
• 393509-10-9 [5-bromo-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 393509-08-5 ethyl [7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 
• 393509-09-6 [7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 251548-94-4 2-iodo-4-(methylsulfonyl)phenylamine 
• 5470-49-5 4-methanesulfonylphenylamine 
• 20826-94-2 ethyl (2-oxocyclopentyl)acetate 
• 393509-11-0 methyl [5-bromo-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 

Downstream Products

• 795281-21-9 [5-acetyl-4-(4-chloro-benzyl)-7-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid 
• 393508-94-6 [5-acetyl-4-(4-chlorobenzyl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 

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.

Cyclopentanoindoles, compositions containing such compounds and methods of treatment

Substituted cyclopentanoindole derivatives are antagonists of prostaglandins, and as such are useful for the treatment of prostaglandin mediated diseases.