136564-68-6

Basic information

• Product Name: (R)-3-Methoxy-4-[1-methyl-5-[N-(2-methyl-4,4,4-trifluorobutyl)carbamoyl]indol-3-ylmethyl]-N-(2-methylphenylsulfonyl)benzamide
• Synonyms: ZD-3523; (R)-3-[2-Methoxy-4-[N-(2-methylphenylsulfonyl)carbamoyl]benzyl]-1-methyl-N-(4,4,4-trifluoro-2-methylbutyl)indole-5-carboxamide; 3-(2-methoxy-4-{[(2-methylphenyl)sulfonyl]carbamoyl}benzyl)-1-methyl-N-[(2R)-4,4,4-trifluoro-2-methylbutyl]-1H-indole-5-carboxamide; Zeneca ZD 3523; Masilukast
• CAS NO: 136564-68-6
• Molecular Formula: C₃₁H₃₂F₃N₃O₅S
• Molecular Weight: 615.6631
• Mol File: 136564-68-6.mol
• Article Data: 2

Chemical Properties

• Density: 1.31g/cm³
• Refractive Index: 1.587
• CAS DataBase Reference: (R)-3-Methoxy-4-[1-methyl-5-[N-(2-methyl-4,4,4-trifluorobutyl)carbamoyl]indol-3-ylmethyl]-N-(2-methylphenylsulfonyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Methoxy-4-[1-methyl-5-[N-(2-methyl-4,4,4-trifluorobutyl)carbamoyl]indol-3-ylmethyl]-N-(2-methylphenylsulfonyl)benzamide(136564-68-6)
• EPA Substance Registry System: (R)-3-Methoxy-4-[1-methyl-5-[N-(2-methyl-4,4,4-trifluorobutyl)carbamoyl]indol-3-ylmethyl]-N-(2-methylphenylsulfonyl)benzamide(136564-68-6)

Safety Data

• Hazardous Substances Data: 136564-68-6(Hazardous Substances Data)

Usage

General Description

"(R)-3-Methoxy-4-[1-methyl-5-[N-(2-methyl-4,4,4-trifluorobutyl)carbamoyl]indol-3-ylmethyl]-N-(2-methylphenylsulfonyl)benzamide" is a complex organic compound. It is characterized by several functional groups, including a methoxy group, a carbamoyl group, a trifluorobutyl group, a benzamide group, and a sulfonyl group. It also includes two different types of aromatic systems, an indole ring and a phenyl ring. The compound's chirality is specified by the (R)-configuration, which indicates the spatial arrangement of the different groups around the chiral center. The exact physical and chemical properties of this compound, such as its melting point, boiling point, solubility, and reactivity, would depend on its specific structure and would need to be determined experimentally.

Upstream product

• 136564-83-5 (R)-2-methyl-4,4,4-trifluorobutylamine hydrochloride 
• 136564-73-3 methyl 4-<<5-carboxy-1-methylindol-3-yl>methyl>-3-methoxybenzoate 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 
• 136564-79-9 (R)-3-methoxy-4-<<1-methyl-5-<(2-methyl-4,4,4-trifluorobutyl)carbamoyl>indol-3-yl>methyl>benzoic acid 
• 136564-84-6 methyl (R)-3-methoxy-4-<<1-methyl-5-<(2-methyl-4,4,4-trifluorobutyl)carbamoyl>indol-3-yl>methyl>benzoate 

Downstream Products

• 143484-03-1 methyl 4-(5-methoxycarbonylindol-3-ylmethyl)-3-methoxybenzoate 
• 143484-12-2 4-(5-methoxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoyl chloride 

Relevant articles and documents

Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of a Series of Fluorinated 3-Benzyl-5-indolecarboxamides: Identification of 4--1-methylindol-3-yl>methyl>-3-methoxy-N-benzamide, ...

The continued exploration of a series of 3-(arylmethyl)-1H-indole-5-carboxamides by the introduction of fluorinated amide substituents has resulted in the discovery of 4--1-methylindol-3-yl>methyl>-3-methoxy-N-benzamide (38p, ZENECA ZD 3523), which has been chosen for clinical evaluation.This compound exhibited a Ki of 0.42 nM for displacement of LTD4 on guinea pig lung membranes, a pKB of 10.13 +/- 0.14 versus LTE4 on guinea pig trachea, and an oral ED50 of 1.14 μmol/kg opposite LTD4-induced bronchoconstriction in guinea pigs.The R enantiomer was found to be modestly more potent than the S enantiomer 38o.Modification of the amide substituent to afford achiral compounds was unsuccessful in achieving comparable levels of activity.Profiling of 38p opposite a variety of functional assays has demonstrated the selectivity of this compound as a leukotriene receptor antagonist.The enantioselective synthesis of 38p, which employed a diastereoselective alkylation of (4R,5S)-3-(1-oxo-4,4,4-trifluorobutyl)-4-methyl-5-phenyl-2-oxazolidinone (27) as the key step to establish the chirality of the amide substituent, provided an efficient route for generating 38p in >99percent enantiomeric purity.