166882-70-8

Basic information

• Product Name: 2H-Indol-2-one,1,3-dihydro-1-methyl-5-[[4-[(2S,4R)-tetrahydro-4-hydroxy-2-methyl-2H-pyran-4-yl]-2-thienyl]thio]-
• Synonyms: 2H-Indol-2-one,1,3-dihydro-1-methyl-5-[[4-(tetrahydro-4-hydroxy-2-methyl-2H-pyran-4-yl)-2-thienyl]thio]-,(2S-trans)-; ZD 4407
• CAS NO: 166882-70-8
• Molecular Formula: C19H21 N O3 S2
• Molecular Weight: 375.513
• Mol File: 166882-70-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2H-Indol-2-one,1,3-dihydro-1-methyl-5-[[4-[(2S,4R)-tetrahydro-4-hydroxy-2-methyl-2H-pyran-4-yl]-2-thienyl]thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Indol-2-one,1,3-dihydro-1-methyl-5-[[4-[(2S,4R)-tetrahydro-4-hydroxy-2-methyl-2H-pyran-4-yl]-2-thienyl]thio]-(166882-70-8)
• EPA Substance Registry System: 2H-Indol-2-one,1,3-dihydro-1-methyl-5-[[4-[(2S,4R)-tetrahydro-4-hydroxy-2-methyl-2H-pyran-4-yl]-2-thienyl]thio]-(166882-70-8)

Safety Data

• Hazardous Substances Data: 166882-70-8(Hazardous Substances Data)

Upstream product

• 166883-20-1 1-methyl-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 
• 61-70-1 N-methyl-2-indolinone 
• 166883-22-3 5-mercapto-1-methylindolin-2-one 
• 166883-21-2 di-(1-methyl-2-oxoindolin-5-yl) disulphide 
• 82110-21-2 (S)-2-methyl-3,4,5,6-tetrahydro-2H-pyran-4-one 
• 3140-92-9 2,4-dibromothiophene 
• 851724-01-1 1-methyl-5-thiocyanato-1,3-dihydro-indol-2-one 
• 14221-01-3 tetrakis(triphenylphosphine) palladium⁽⁰⁾ 
• 20870-90-0 5-bromo-1-methyl-1,3-dihydro-indol-2-one 
• 166882-94-6 (2S,4R)-4-hydroxy-4-(2-mercaptothien-4-yl)-2-methyltetrahydropyran 

Relevant articles and documents

Efficient syntheses of AZD4407 via thioether formation by nucleophilic attack of organometallic species on sulphur

The development of two efficient strategies for the synthesis of AZD4407 is reported, both of which are considered suitable for large-scale manufacture. In the first approach, 3-bromothiophene is coupled with (2S)-2- methyltetrahydropyran-4-one using Grignard chemistry. Following hydroxyl protection and lithiation at thiophene C-2, reaction with a protected 5-mercapto-1-methyl-1,3-dihydro-indol-2-one derivative bearing a leaving group on sulphur provides AZD4407 after acid-catalysed deprotection and epimerisation. The second approach starts from 2,4-dibromothiophene, which undergoes a selective Grignard exchange reaction at C-2 followed by reaction with similar protected mercapto-oxindole derivatives. Reprotection of the oxindole ring, followed by a second Grignard exchange, and reaction with (2S)-2- methyltetrahydropyran-4-one provides AZD4407 after acid-catalysed deprotection and epimerisation.

ETHER DERIVATIVES HAVING 5-LIPOXYGENASE INHIBITORY ACTIVITY

The invention concerns ether derivatives of the formula I Q1?X?Ar?Q2 wherein Q1 is an optionally substituted 9-, 10- or 11-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur; X is oxy, thio, sulphinyl or sulphonyl; Ar is optionally substituted phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl, thiazolediyl, oxazoiediyl, thiadiazoiediyl or oxadiazolediyl; and Q2 is selected from the groups of the formulae II and III: wherein R1 is hydrogen, (2-5C)alkanoyl or optionally substituted benzoyl; R2 is (l-4C)alkyl; and R3 is hydrogen or (l-4C)alkyl; or R2 and R3 are linked to form a methylene, vinylene, ethylene or trimethylene group; or a pharmaceutically-acceptable salt thereof; processes for their preparation; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.