107754-19-8

Basic information

• Product Name: 4-[[5-[[(Cyclopentyloxy)carbonyl]aMino]-1-Methyl-1H-indol-3-yl]Methyl]-3-Methoxy-benzoic Acid Methyl Ester
• Synonyms: 4-[[5-[[(Cyclopentyloxy)carbonyl]aMino]-1-Methyl-1H-indol-3-yl]Methyl]-3-Methoxy-benzoic Acid Methyl Ester
• CAS NO: 107754-19-8
• Molecular Formula: C₂₅H₂₈N₂O₅
• Molecular Weight: 438.5161
• Product Categories: Heterocycles, Impurities, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 107754-19-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 128-132 °C
• Boiling Point: 581.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• PKA: 14.52±0.43(Predicted)
• CAS DataBase Reference: 4-[[5-[[(Cyclopentyloxy)carbonyl]aMino]-1-Methyl-1H-indol-3-yl]Methyl]-3-Methoxy-benzoic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[[5-[[(Cyclopentyloxy)carbonyl]aMino]-1-Methyl-1H-indol-3-yl]Methyl]-3-Methoxy-benzoic Acid Methyl Ester(107754-19-8)
• EPA Substance Registry System: 4-[[5-[[(Cyclopentyloxy)carbonyl]aMino]-1-Methyl-1H-indol-3-yl]Methyl]-3-Methoxy-benzoic Acid Methyl Ester(107754-19-8)

Safety Data

• Hazardous Substances Data: 107754-19-8(Hazardous Substances Data)

Usage

Uses

4-[[5-[[(Cyclopentyloxy)carbonyl]amino]-1-methyl-1H-indol-3-yl]methyl]-3-methoxy-benzoic Acid Methyl Ester is an impurity of Zafirlukast (Z125000), a potent, selective and orally active cysteinyl leukotriene type 1 receptor antagonist.

Upstream product

• 70264-94-7 methyl 4-(bromomethyl)-3-methoxybenzoate 
• 3556-83-0 methyl 4-methyl-3-methoxybenzoate 
• 29906-67-0 1-methyl-5-nitro-1H-indole 
• 7151-68-0 3-methoxy-p-toluic acid 
• 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 
• 50715-28-1 cyclopentyl chloroformate 
• 107754-14-3 methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate 

Downstream Products

• 126502-34-9 {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester 
• 126502-33-8 {3-[4-(2-Chloro-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester 
• 126502-32-7 {3-[2-Methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester 
• 107753-78-6 ZAFIRLUKAST 
• 107753-53-7 N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoyl]benzenesulphonamide 
• 107754-31-4 cyclopentyl N-[3-({4-[(benzenesulfonyl)carbamoyl]-2-methoxyphenyl}methyl)-1-methyl-1H-indol-5-yl]carbamate 
• 107786-91-4 methyl 4-[2-(acetoxyimino)-2-[5-(cyclopentyloxycarbonyl)amino-2-(methylamino)phenyl]ethyl]-3-methoxybenzoate 
• 107786-93-6 methyl 4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(methylamino)phenyl>-2-(hydroxyimino)ethyl>-3-methoxybenzoate 
• 107786-90-3 methyl 4-<<5-<<(cyclopentyloxy)carbonyl>amino>-1-methylindazol-3-yl>methyl>-3-methoxybenzoate 
• 107786-94-7 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid 
• 107786-92-5 methyl 4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(N-formyl-N-methylamino)phenyl>-2-oxoethyl>-3-methoxybenzoate 
• 107754-20-1 4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxy-benzoic acid 

Relevant articles and documents

Dual Farnesoid X Receptor/Soluble Epoxide Hydrolase Modulators Derived from Zafirlukast

The nuclear farnesoid X receptor (FXR) and the enzyme soluble epoxide hydrolase (sEH) are validated molecular targets to treat metabolic disorders such as non-alcoholic steatohepatitis (NASH). Their simultaneous modulation in vivo has demonstrated a triad of anti-NASH effects and thus may generate synergistic efficacy. Here we report dual FXR activators/sEH inhibitors derived from the anti-asthma drug Zafirlukast. Systematic structural optimization of the scaffold has produced favorable dual potency on FXR and sEH while depleting the original cysteinyl leukotriene receptor antagonism of the lead drug. The resulting polypharmacological activity profile holds promise in the treatment of liver-related metabolic diseases.

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.

SUBSTITUTED INDOLES

Disclosed herein are substituted indole cysteinyl leukotriene receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.