104447-78-1

Basic information

• Product Name: 6-indole
• Synonyms: 6-indole
• CAS NO: 104447-78-1
• Molecular Formula: C₁₅H₁₈N₂O
• Molecular Weight: 242.32
• Mol File: 104447-78-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-indole(104447-78-1)
• EPA Substance Registry System: 6-indole(104447-78-1)

Safety Data

• Hazardous Substances Data: 104447-78-1(Hazardous Substances Data)

Upstream product

• 1670-82-2 Indole-6-carboxylic acid 
• 6053-81-2 cyclopentylmethylamine 
• 50820-65-0 indole-6-carboxylic acid methyl ester 
• 7356-11-8 4-methyl-3-nitro-benzoic acid methyl ester 
• 104447-80-5 (E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]ethene 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 104447-79-2 methyl 4-<<6-indol-1-yl>methyl>-3-methoxybenzoate 
• 104448-21-7 4-[6-(N-cyclopentylmethyl)carbamoylindol-1-ylmethyl]-3-methoxybenzoic acid 
• 104448-73-9 N-(4-[6-(N-cyclopentylmethylcarbamoyl)indol-1-ylmethyl]-3-methoxybenzoyl)benzenesulphonamide 

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.

Indazole compounds, pharmaceutical compositions and use

The invention provides a series of novel heterocyclic amides of the formula I in which the group A CRa can be --CRb=CRa--, --CHRb--CHRa-- or --N=CRa--, the amidic group Re.L can be Re.X.CO.NH, Re.X.CS.NH or Re.NH.CO attached at position 4, 5 or 6 of the benzenoid moiety, Z is an acid group selected from the group consisting of carboxy, an acylsulphonamide residue of the formula CO.NH.SOn Rg and a tetrazolyl residue of the formula II, and the radicals Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, n, X, G1, Q and G2 have the meanings defined in the following specification. The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compounds, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.