142563-81-3

Basic information

• Product Name: 3-[1-(4-Benzenesulfonylaminocarbonyl-2-methoxy-benzyl)-6-(2-cyclopentyl-ethoxy)-1H-indol-3-yl]-propionamide
• Synonyms: 3-[1-(4-Benzenesulfonylaminocarbonyl-2-methoxy-benzyl)-6-(2-cyclopentyl-ethoxy)-1H-indol-3-yl]-propionamide
• CAS NO: 142563-81-3
• Molecular Weight: 603.739
• Mol File: 142563-81-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-[1-(4-Benzenesulfonylaminocarbonyl-2-methoxy-benzyl)-6-(2-cyclopentyl-ethoxy)-1H-indol-3-yl]-propionamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[1-(4-Benzenesulfonylaminocarbonyl-2-methoxy-benzyl)-6-(2-cyclopentyl-ethoxy)-1H-indol-3-yl]-propionamide(142563-81-3)
• EPA Substance Registry System: 3-[1-(4-Benzenesulfonylaminocarbonyl-2-methoxy-benzyl)-6-(2-cyclopentyl-ethoxy)-1H-indol-3-yl]-propionamide(142563-81-3)

Safety Data

• Hazardous Substances Data: 142563-81-3(Hazardous Substances Data)

Upstream product

• 2380-86-1 6-hydroxy-1H-indole 
• 99474-13-2 (E)-5-(benzyloxy)-2-<2-(dimethylamino)vinyl>nitrobenzene 
• 142535-29-3 tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate 
• 142535-31-7 4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethyl>indol-1-yl>methyl>-3-methoxybenzoic acid 
• 142535-30-6 (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoic acid 
• 142535-28-2 tert-butyl 4-<<6-(2-cyclopentylethoxy)-3-formylindol-1-yl>methyl>-3-methoxybenzoate 
• 142535-27-1 6-(2-cyclopentylethoxy)-3-formylindole 
• 142535-22-6 6-(2-cyclopentylethoxy)indole 
• 24239-67-6 4-(benzyloxy)-1-methyl-2-nitrobenzene 
• 766-00-7 2-cyclopentyl-ethanol 
• 98-10-2 benzenesulfonamide 
• 142535-32-8 4-<<6-(2-cyclopentylethoxy)-3-(2-carbamoylethyl)indol-1-yl>methyl>-3-methoxybenzoic acid 

Relevant articles and documents

1,3,6-Trisubstituted indoles as peptidoleukotriene antagonists: Benefits of a second, polar, pyrrole substituent

1,6-Substituted and 3,5-substituted indoles and indazoles containing acylamino and N-arylsulfonyl amide appendages are potent antagonists of the peptidoleukotrienes LTD4 and LTE4. A compound from the 3,5-substituted indole series, N-[4-[[5-[[(cyclopentyloxy)carbonyl]amino]-1-methylindol-3- yl]methyl]-3-methoxybenzoyl]-2-methyl-benzenesulfonamide (ICI 204,219), is undergoing clinical evaluation for asthma. Two new elements of structural diversity were introduced to this series of antagonists. An investigation of pyrrole substituents in the 1,6-substituted indoles demonstrated that substitution at C-2 was detrimental to biological activity, but the incorporation of hydrophilic groups at C-3 was beneficial. The introduction of a propionamide moiety at C-3 enhanced activity by 1 order of magnitude; N- [4-[[6-(cyclopentylacetamido)-3-[2-(N-methylcarbamoyl)ethyl]indol-1- yl]methyl]-3-methoxybenzoyl]benzenesulfonamide (15c) has a pK(B) of 10.7 at the LTD4 receptor on guinea pig trachea. Modifications of the acylamino portion of the disubstituted antagonists demonstrated that a transposition of the amide CO and NH atoms was viable. N-Cyclopentylmethyl amides in both the 1,6- and 3,5-disubstituted indole series were 1 order of magnitude less potent than the corresponding cyclopentylacetamides. In both series this potency loss could be regained by the incorporation of a propionamide substituent at either C-3 or N-1, respectively. For example, N-[4-[[6-[N- (cyclopentylmethyl)carbamoyl]-3-[2-(pyrrolidin-1-ylcarbonyl)ethyl]indol-1- yl]methyl]-3-methoxybenzoyl]-2-methylbenzenesulfonamide (39c) has a pK(B) of 9.5.