54666-28-3

Basic information

• Product Name: 8-HYDROXY-4-(1H-IMIDAZOL-YL)-2-METHYLQUINOLINE
• Synonyms: 8-HYDROXY-4-(1H-IMIDAZOL-YL)-2-METHYLQUINOLINE;8-Hydroxy-4-(1H-imidazol-1-yl)-2-methylquinoline;4-(1H-imidazol-1-yl)-2-methyl-8-Quinolinol
• CAS NO: 54666-28-3
• Molecular Formula: C₁₃H₁₁N₃O
• Molecular Weight: 225.25
• Mol File: 54666-28-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 477.3°C at 760 mmHg
• Flash Point: 242.5°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 9.81E-10mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 8-HYDROXY-4-(1H-IMIDAZOL-YL)-2-METHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-HYDROXY-4-(1H-IMIDAZOL-YL)-2-METHYLQUINOLINE(54666-28-3)
• EPA Substance Registry System: 8-HYDROXY-4-(1H-IMIDAZOL-YL)-2-METHYLQUINOLINE(54666-28-3)

Safety Data

• Hazardous Substances Data: 54666-28-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H11N3O/c1-9-7-11(16-6-5-14-8-16)10-3-2-4-12(17)13(10)15-9/h2-8,17H,1H3

Upstream product

• 288-32-4 1H-imidazole 
• 28507-46-2 4-chloro-8-hydroxy-2-methylquinoline 
• 144-55-8 sodium hydrogencarbonate 
• 90-04-0 2-methoxy-phenylamine 
• 33267-45-7 ethyl 3-<(2-methoxyphenyl)amino>but-2-enoate 
• 64951-58-2 4-chloro-8-methoxy-2-methylquinoline 
• 15644-89-0 8-methoxy-2-methyl-4-quinolinol 

Downstream Products

• 290345-05-0 1-[[3-(Bromomethyl)-2,4-dichlorophenyl]sulphonyl]-2(S)-(methoxymethyl)-pyrrolidine 
• 290342-79-9 1-[[2,4-Dichloro-3-[[[4-(1H-imidazol-1-yl)-2-methyl-8-quinolinyl)oxy]methyl]-phenyl]sulphonyl]-2(S)-(methoxymethyl)pyrrolidine 
• 290344-80-8 1-[[3-(Bromomethyl)-2,4-dichlorophenyl]sulphonyl]-2(S)-pyrrolidinemethanol 
• 290341-94-5 1-[[2,4-Dichloro-3-[[[4-(1H-imidazol-1-yl)-2-methyl-8-quinolinyl]oxy]methyl]-phenyl]sulphonyl]-2(S)-pyrrolidinemethanol 
• 199106-15-5 2-amino-N-[2,4-dichloro-3-({[4-(1H-imidazol-1-yl)-2-methyl-8-quinolinyl]oxy}methyl)phenyl]-N-methylacetamide 
• 189267-30-9 1-[2,4-dichloro-3-[4-(imidazol-1-yl)-2-methylquinolin-8-yloxymethyl]phenyl]-2-(propionamidomethyl)pyrrole 

Relevant articles and documents

Novel small molecule bradykinin B2 receptor antagonists

Blockade of the bradykinin B2 receptor provides therapeutic benefit in hereditary angioedema (HAE) and potentially in many other diseases. Herein, we describe the development of highly potent B2 receptor antagonists with a molecular weight of approximately 500 g/mol. First, known quinoline-based B2 receptor antagonists were stripped down to their shared core motif 53, which turned out to be the minimum pharmacophore. Targeted modifications of 53 resulted in the highly water-soluble lead compound 8a. Extensive exploration of its structure-activity relationship resulted in a series of highly potent B2 receptor antagonists, featuring a hydrogen bond accepting functionality, which presumably interacts with the side chain of Asn-107 of the B2 receptor. Optimization of the microsomal stability and cytochrome P450 inhibition eventually led to the discovery of the highly potent and orally available B2 receptor antagonist 52e (JSM10292), which showed the best overall properties.

A New Series of Highly Potent Non-Peptide Bradykinin B2 Receptor Antagonists Incorporating the 4-Heteroarylquinoline Framework. Improvement of Aqueous Solubility and New Insights into Species Difference

Introduction of nitrogen-containing heteroaromatic groups at the 4-position of the quinoline moiety of our non-peptide B2 receptor antagonists resulted in enhancing binding affinities for the human B 2 receptor and reducing binding affinities for the guinea pig one, providing new structural insights into species difference. A CoMFA study focused on the diversity of the quinoline moiety afforded correlative and predictive QSAR models of binding for the human B2 receptor but not for the guinea pig one. A series of 4-(1-imidazolyl)quinoline derivatives could be dissolved in a 5% aqueous solution of citric acid up to a concentration of 10 mg/mL. A representative compound 48a inhibited the specific binding of [ 3H]BK to the cloned human B2 receptor expressed in Chinese hamster ovary cells with an IC50 value of 0.26 nM and significantly inhibited BK-induced bronchoconstriction in guinea pigs even at 1 μg/kg by intravenous administration.

Quinoline derivatives, processes for their preparation and their use as medicaments

PCT No. PCT/JP97/01415 Sec. 371 Date Oct. 26, 1998 Sec. 102(e) Date Oct. 26, 1998 PCT Filed Apr. 24, 1997 PCT Pub. No. WO97/15877 PCT Pub. Date Apr. 24, 1997A compound of the formula: wherein R1 is lower alkyl, R2 is hydrogen, lower alkyl or a heterocyclic group, R3 is hydrogen, lower alkyl or halogen, R4 is lower alkyl or halogen, R5 is nitro or amino substituted with substituent(s) selected from the group consisting of lower alkyl and acyl, and A is lower alkylene.