149167-98-6

Basic information

• Product Name: 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(thiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropionic acid
• CAS NO: 149167-98-6
• Molecular Weight: 543.151
• Mol File: 149167-98-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(thiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(thiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropionic acid(149167-98-6)
• EPA Substance Registry System: 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(thiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropionic acid(149167-98-6)

Safety Data

• Hazardous Substances Data: 149167-98-6(Hazardous Substances Data)

Upstream product

• 136694-17-2 methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropionate 
• 148693-71-4 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoic acid 
• 136558-13-9 ethyl 5-t-butylthio-2,2-dimethyl-4-oxo-pentanoate 
• 147961-24-8 3-[1-(4-Chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoic acid 
• 62646-04-2 1-(4-chlorobenzyl)-1-(4-methoxyphenyl)hydrazine 

Relevant articles and documents

Substituted indoles as potent and orally active 5-lipoxygenase activating protein (FLAP) inhibitors

This paper reports on the SAR investigation of inhibitors of 5- lipoxygenase activating protein (FLAP) based on MK-0591. Emphasis was made on modifications to the nature of the link between the indole and the quinoline moieties, to the substitution pattern around the two heterocycles and to possible replacements of the quinoline moiety. Lead optimization culminated in (3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(pyridin-2-ylmethoxy)-indol-2- yl]-2,2-dimethylpropanoic acid (18k), as a potent inhibitor of leukotriene biosynthesis that is well absorbed and active in functional models.

INDOLE CARBOXYLATE DERIVATIVES WHICH INHIBIT LEUKOTRIENE BIOSYNTHESIS

Compounds of the structure where A is straight or branched divalent alkylene or divalent cycloalkylene, R1 is selected from hydrogen; alkylthio; optionally substituted phenylthio; optionally substituted phenylalkylthio; optionally substituted 2-, 3-, and 4-pyridyl; optionally substituted 2-, and 3-thienylthio; and optionally substituted 2-thiazolythio, R2 is selected from -COOB; -COOalkyl; -COOalkyl(carbocyclic aryl); -CONR5R6 ; -COR6 ; and -OH, R3 is selected from phenylalkyl and heteroarylalkyl, and R4 is selected from optionally substituted alkoxy(carbocyclic aryl); optionally substituted carbocyclic aryloxy; optionally substituted heteroarylalkoxy; and optionally substituted heteroaryloxy are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states