73384-60-8

Basic information

• Product Name: 2-[2-METHOXY-4-(METHYLSULFINYL)PHENYL]-1H-IMIDAZO[4,5-B]PYRIDINE
• Synonyms: 2-[2-METHOXY-4-(METHYLSULFINYL)PHENYL]-1H-IMIDAZO[4,5-B]PYRIDINE;SULMAZOLE;5-b)pyridine,2-(2-methoxy-4-(methylsulfinyl)phenyl)-1h-imidazo(;ar-l115bs;2-(2-methoxy-4-(methylsulfinyl)phenyl)-3H-imidazo[4,5-b]pyridine
• CAS NO: 73384-60-8
• Molecular Formula: C₁₄H₁₃N₃O₂S
• Molecular Weight: 287.34
• EINECS: 277-406-1
• Mol File: 73384-60-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 203-205°
• Boiling Point: 577.7°C at 760 mmHg
• Flash Point: 303.2°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 2.41E-13mmHg at 25°C
• Refractive Index: 1.722
• Storage Temp.: 2-8°C
• PKA: 6?+-.0.20(Predicted)
• CAS DataBase Reference: 2-[2-METHOXY-4-(METHYLSULFINYL)PHENYL]-1H-IMIDAZO[4,5-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-METHOXY-4-(METHYLSULFINYL)PHENYL]-1H-IMIDAZO[4,5-B]PYRIDINE(73384-60-8)
• EPA Substance Registry System: 2-[2-METHOXY-4-(METHYLSULFINYL)PHENYL]-1H-IMIDAZO[4,5-B]PYRIDINE(73384-60-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NJ5749500
• Hazardous Substances Data: 73384-60-8(Hazardous Substances Data)

Usage

Description

2-[2-METHOXY-4-(METHYLSULFINYL)PHENYL]-1H-IMIDAZO[4,5-B]PYRIDINE is an imidazopyridine compound that features a 1H-imidazo[4,5-b]pyridine core substituted at position 2 by a 2-methoxy-4-(methylsulfinyl)phenyl group. It acts as an A1 adenosine receptor antagonist and was previously utilized as a cardiac tonic agent.

Uses

Used in Pharmaceutical Industry:
2-[2-METHOXY-4-(METHYLSULFINYL)PHENYL]-1H-IMIDAZO[4,5-B]PYRIDINE is used as a pharmaceutical agent for its A1 adenosine receptor antagonist properties, which were beneficial in the treatment of cardiac conditions as a cardiac tonic agent.

InChI:InChI=1/C14H13N3O2S/c1-19-12-8-9(20(2)18)5-6-10(12)13-16-11-4-3-7-15-14(11)17-13/h3-8H,1-2H3,(H,15,16,17)

Upstream product

• 77414-25-6 2-(2'-methoxy-4'-methylmercapto-phenyl)-1H-imidazo[4,5-b]pyridine 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 77414-25-6 2-(2-Methoxy-4-methylsulfanyl-phenyl)-3H-imidazo[4,5-b]pyridine 

Downstream Products

• 77439-55-5 6'-hydroxy-2-<2-methoxy-4-(methylsulfinyl)phenyl>-1H-imidazo<4,5-b>pyridine 
• 77414-25-6 2-(2'-methoxy-4'-methylmercapto-phenyl)-1H-imidazo[4,5-b]pyridine 
• 77414-25-6 2-(2-Methoxy-4-methylsulfanyl-phenyl)-3H-imidazo[4,5-b]pyridine 
• 77414-24-5 2-(4-Methanesulfonyl-2-methoxy-phenyl)-3H-imidazo[4,5-b]pyridine 

Relevant articles and documents

Structure-activity relationships of arylimidazopyridine cardiotonics: Discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine

Recently several noncatecholamine, nonglycoside cardiotonic drugs have been discovered that possess both inotropic and vasodilator activities in experimental animals and man. Prototypical compounds include amrinone, sulmazole, and fenoximone. We investigated the structural requirements necessary for optimal inotropic activity in a series of molecules containing a heterocyclic ring fused to 2-phenylimidazole and discovered that 2-phenylimidazo[4,5-c]pyridines were generally 5-10-fold more potent than analogous 2-phenylimidazo[4,5-b]pyridines (e.g., sulmazole) or 8-phenylpurines. Furthermore, all imidazo[4,5-c]pyridine analogues we tested were orally active; in contrast, only one of the imidazo[4,5-b]pyridine derivatives, sulmazole, was significantly active. One of several highly active compounds in the [4,5-c] series was 50 (LY175326, 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H- imidazo[4,5-c]pyridine hydrochloride). The structure-activity relationship of this series is presented and compared to that of the imidazo[4,5-b]pyridine and purine series.