107786-49-2

Basic information

• Product Name: methyl 4-<<5-(2-cyclopentylacetamido)-1-methylindol-3-yl>methyl>-3-methoxybenzoate
• Synonyms: methyl 4-<<5-(2-cyclopentylacetamido)-1-methylindol-3-yl>methyl>-3-methoxybenzoate
• CAS NO: 107786-49-2
• Molecular Weight: 434.535
• Mol File: 107786-49-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 4-<<5-(2-cyclopentylacetamido)-1-methylindol-3-yl>methyl>-3-methoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-<<5-(2-cyclopentylacetamido)-1-methylindol-3-yl>methyl>-3-methoxybenzoate(107786-49-2)
• EPA Substance Registry System: methyl 4-<<5-(2-cyclopentylacetamido)-1-methylindol-3-yl>methyl>-3-methoxybenzoate(107786-49-2)

Safety Data

• Hazardous Substances Data: 107786-49-2(Hazardous Substances Data)

Upstream product

• 29906-67-0 1-methyl-5-nitro-1H-indole 
• 6146-52-7 5-nitroindole 
• 107754-15-4 3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)-benzoic acid methyl ester 
• 107786-36-7 4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester 
• 70264-94-7 methyl 4-(bromomethyl)-3-methoxybenzoate 
• 1123-00-8 2-cyclopentylacetic acid 
• 107754-14-3 methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate 

Downstream Products

• 107786-57-2 4-{[5-(2-cyclopentylacetamido)-1-methyl-1H-indol-3-yl]methyl}-3-methoxybenzoic acid 

Relevant articles and documents

Breathing new life into West Nile virus therapeutics; discovery and study of zafirlukast as an NS2B-NS3 protease inhibitor

The West Nile virus (WNV) has spread throughout the world causing neuroinvasive diseases with no treatments available. The viral NS2B-NS3 protease is essential for WNV survival and replication in host cells and is a promising drug target. Through an enzymatic screen of the National Institute of Health clinical compound library, we report the discovery of zafirlukast, an FDA approved treatment for asthma, as an inhibitor for the WNV NS2B-NS3 protease. Zafirlukast was determined to inhibit the protease through a mixed mode mechanism with an IC50 value of 32 μM. A structure activity relationship study of zafirlukast revealed the cyclopentyl carbamate and N-aryl sulfonamide as structural elements crucial for NS2B-NS3 protease inhibition. Replacing the cyclopentyl with a phenyl improved inhibition, resulting in an IC50 of 22 μM. Experimental and computational docking analysis support the inhibition model of zafirlukast and analogs binding at an allosteric site on the NS3 protein, thereby disrupting the NS2B cofactor from binding, resulting in protease inhibition.