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

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

Used in Pharmaceutical Industry:
Methyl-Benzoate,Zafirlukast, is used as an intermediate compound for the synthesis of Zafirlukast (Z125000), which is a potent, selective, and orally active cysteinyl leukotriene type 1 receptor antagonist. This makes it a crucial component in the development of medications targeting various respiratory and inflammatory conditions.
Used in Respiratory Treatments:
Methyl-Benzoate,Zafirlukast, is used as a key component in the development of Zafirlukast, which is an effective treatment for asthma and allergic rhinitis. By acting as a leukotriene receptor antagonist, Zafirlukast helps to reduce inflammation and constriction in the airways, providing relief from respiratory symptoms.
Used in Inflammatory Condition Management:
Methyl-Benzoate,Zafirlukast, contributes to the development of Zafirlukast, which is also used in managing other inflammatory conditions such as eosinophilic esophagitis. By blocking the action of leukotrienes, Zafirlukast can help to alleviate symptoms and improve the quality of life for patients suffering from these conditions.

Upstream product

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

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

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

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.

Synthetic method of zukast intermediate

The invention discloses a synthesis method of a Zarustra intermediate. The synthesis method of the Zarustra intermediate is characterized in that by comprising the steps of a, adding 5-nitroindole toan organic solvent, slowly adding metal hydride, conduct

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.

Boosting Anti-Inflammatory Potency of Zafirlukast by Designed Polypharmacology

Multitarget design offers access to bioactive small molecules with potentially superior efficacy and safety. Particularly multifactorial chronic inflammatory diseases demand multiple pharmacological interventions for stable treatment. By minor structural changes, we have developed a close analogue of the cysteinyl-leukotriene receptor antagonist zafirlukast that simultaneously inhibits soluble epoxide hydrolase and activates peroxisome proliferator-activated receptor γ. The triple modulator exhibits robust anti-inflammatory activity in vivo and highlights the therapeutic potential of designed multitarget agents.

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.

An improved and scalable process for zafirlukast: An asthma drug

An improved and scalable process for the large-scale production of zafirlukast (Accolate), an important drug for asthma, is discussed along with impurity and scale-up-related issues.

PROCESSES FOR PREPARING ZAFIRLUKAST

An improved process for the preparation of substantially pure zafirlukast and pharmaceutical compositions thereof.

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.