107754-15-4

Basic information

• Product Name: Methyl-Benzoate,Zafirlukast,
• Synonyms: Methyl-Benzoate,Zafirlukast,;Methyl-3-Methoxy-4-[(1-Methyl-5-Nitro 1H-Indol-3-yl) Methyl]-Benzoate;Benzoic acid, 3-Methoxy-4-[(1-Methyl-5-nitro-1H-indol-3-yl)Methyl]-, Methyl ester
• CAS NO: 107754-15-4
• Molecular Formula: C₁₉H₁₈N₂O₅
• Molecular Weight: 354.35662
• Mol File: 107754-15-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 149-150 °C
• Boiling Point: 542.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Methyl-Benzoate,Zafirlukast,(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-Benzoate,Zafirlukast,(107754-15-4)
• EPA Substance Registry System: Methyl-Benzoate,Zafirlukast,(107754-15-4)

Safety Data

• Hazardous Substances Data: 107754-15-4(Hazardous Substances Data)

Usage

Uses

Methyl 3-Methoxy-4-[(1-methyl-5-nitro-1H-indol-3-yl)methyl]benzoate is an intermediate in the synthesis of Methyl 4-[(5-Amino-1-methylindol-3-yl)methyl]-3-methoxybenzoate (M258650), also an intermediate in the preparation of Zafirlukast (Z125000), a potent, selective and orally active cysteinyl leukotriene type 1 receptor antagonist.

Upstream product

• 7151-68-0 3-methoxy-p-toluic acid 
• 3556-83-0 methyl 4-methyl-3-methoxybenzoate 
• 74-88-4 methyl iodide 
• 849758-14-1 4-(methoxycarbonyl)-2-methoxyphenylboronic acid 
• 3558-10-9 5-nitro-1-methyl-1H-indole-3-carbaldehyde 
• 6625-96-3 5-nitro-1H-indole-3-carbaldehyde 
• 29906-67-0 1-methyl-5-nitro-1H-indole 
• 70264-94-7 methyl 4-(bromomethyl)-3-methoxybenzoate 
• 107786-36-7 4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester 
• 6146-52-7 5-nitroindole 

Downstream Products

• 107754-14-3 methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate 
• 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 
• 126502-31-6 2-Chloro-N-{4-[5-(3-cyclopentyl-ureido)-1-methyl-1H-indol-3-ylmethyl]-3-methoxy-benzoyl}-benzenesulfonamide 
• 126502-32-7 {3-[2-Methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester 
• 126502-29-2 N-{3-[4-(2-Chloro-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide 
• 107753-78-6 ZAFIRLUKAST 

Relevant articles and documents

Ferric Chloride Catalyzed 1,3-Rearrangement of (Phenoxymethyl)heteroarenes to (Heteroarylmethyl)phenols

A highly useful and robust method to (heteroarylmethyl)phenols, derivatives of arylheteroarylmethanes, was developed based on iron(III)-catalyzed 1,3-rearrangement of (phenoxymethyl)heteroarenes. It features cheap catalyst, mild reaction conditions, short

Proton-exchanged montmorillonite-mediated reactions of hetero-benzyl acetates: Application to the synthesis of Zafirlukast

Proton-exchanged montmorillonite (H-mont) with outstanding surface characteristics can provide abundant acidic sites in the mesopores, and serve as an efficient heterogeneous catalyst for the synthesis of heterocycle-containing diarylmethanes via Friedel-Crafts-like alkylation of (hetero)arenes by heterobenzyl acetates under mild reaction conditions without requiring any additives or an inert atmosphere. Using this strategy, the gram-scale synthesis of indole-containing diarylmethane 13 has been accomplished in good yield for the preparation of Zafirlukast. In addition, H-mont can be applied to the nucleophilic substitution reactions of heterobenzyl acetate 5p with a variety of alcohols and 1,3-dicarbonyl compounds.

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.