124993-40-4

Basic information

• Product Name: 4-(2-Quinolinylmethoxy)phenol
• Synonyms: 4-(2-Quinolinylmethoxy)phenol;Phenol, 4-(2-quinolinylmethoxy)-;4-(QUINOLIN-2-YL)METHOXYPHENOL(WXG01246)
• CAS NO: 124993-40-4
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.27992
• Mol File: 124993-40-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(2-Quinolinylmethoxy)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Quinolinylmethoxy)phenol(124993-40-4)
• EPA Substance Registry System: 4-(2-Quinolinylmethoxy)phenol(124993-40-4)

Safety Data

• Hazardous Substances Data: 124993-40-4(Hazardous Substances Data)

Upstream product

• 125439-41-0 4-(2-quinolinylmethoxy)phenyl benzoate 
• 1076-28-4 2-methylquinoline N-oxide 
• 123-31-9 hydroquinone 
• 187879-24-9 1-(4-Hydroxy-phenoxy)-3-(triphenyl-λ⁵-phosphanylidene)-propan-2-one 
• 4377-41-7 2-Chloromethylquinoline 
• 2444-19-1 4-hydroxyphenyl benzoate 
• 3747-74-8 2-(chloromethyl)quinoline monohydrochloride 
• 91-63-4 2-methylquinoline 

Downstream Products

• 125439-20-5 4-[4-(Quinolin-2-ylmethoxy)-phenoxy]-butyric acid ethyl ester 
• 124993-48-2 2-<<4-(2-quinolinylmethoxy)phenoxy>methyl>benzyl chloride 
• 123225-68-3 α-(3-(4-(2-quinolinylmethyloxy)phenoxymethyl)phenoxy) acetonitrile 
• 124993-52-8 2-<<4-(2-quinolinylmethoxy)phenoxy>methyl>phenoxyacetonitrile 
• 188255-05-2 2-{4-[2-(2-Trityl-2H-tetrazol-5-ylmethyl)-benzyloxy]-phenoxymethyl}-quinoline 
• 120128-20-3 2-[[4-[[2-(1H-tetrazol-5-ylmethyl)phenyl]methoxy]phenoxy]methyl]quinoline 
• 124993-49-3 2-<<4-(2-quinolinylmethoxy)phenoxy>methyl>benzyl cyanide 
• 125439-19-2 4-[4-(Quinolin-2-ylmethoxy)-phenoxy]-butyric acid 
• 123225-95-6 5-(3-(4-(2-quinolinylmethyloxy)phenoxymethyl)phenyl)-tetrazole 
• 123225-98-9 5-(4-(4-(2-quinolinylmethyloxy)phenoxymethyl)benzyl)tetrazole 
• 125439-18-1 N-{4-[4-(Quinolin-2-ylmethoxy)-phenoxy]-butyryl}-benzenesulfonamide 
• 123247-23-4 5-(3-(4-(2-QUINOLINYLMETHYLOXY)-PHENOXYMETHYL)PHENOXYMETHYL)TETRAZOLE 
• 128760-43-0 4-(2-(4-((quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)-4-carboxybutyric acid 
• 128760-77-0 ethyl 2,3-oxido-3-(2-(4-((quinolin-2-yl)methyloxy)phenoxymethyl)phenyl)propionate 

Relevant articles and documents

The process development of RG 12525 (2-{[4-(Tetrazol-5-ylmethylphenyl)-methoxy]phenoxymethyl}quinoline)

This contribution describes process improvements to provide a practical and cost-effective synthesis for the manufacture of RG 12525 which resulted in a 3-fold increase in overall yield. Improved solvent systems for chlorination and azidation reactions are described. Adjustments to the tetrazole-forming step eliminated azide sublimation and minimised this risk on scale-up. A robust solvent system was found to control the polymorphic form during crystallisation, which had hitherto been difficult due to the near-equivalence of melting points (154 and 157 °C) of the two known forms.

Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 1. Initial structure-activity relationships

This series of reports describes the development of orally active, highly potent, specific antagonists of the peptidoleukotrienes containing a (2-quinolinylmethoxy)phenyl moiety. Described in this first report are the structure-activity relationships that led to more than a 20-fold improvement of the potency and selectivity of the initial chemical lead (RG 5901). From this series of compounds, RG 7152 (16) was identified and selected for further evaluation in the clinic as an antiasthmatic agent. Compound 16 competitively inhibits [3H]LTD4 binding to membranes from guinea pigs lung (K(i) = 38 ± 6 nM) and the spasmogenic activity of LTC4, LTD4, and LTE4 in parenchymal lung strips from guinea pigs. Unlike the original lead (RG 5901), compound 16 does not inhibit 5-lipoxygenase from guinea pig PMNs. Following oral administration to guinea pigs, 16 blocks LTD4-induced dermal permeability (ED50 = 6.9 mg/kg), LTD4-induced bronchoconstriction (ED50 = 1.1 mg/kg), antigen-induced bronchoconstriction (ED50 = 2.5 mg/kg), and anaphylactic-induced mortality (ED50 = 16 mg/kg). These studies on structure-activity relationships indicate that there is a requirement for an acidic function and the presence of the (2-quinolinylmethoxy)phenyl moiety in a specific geometric arrangement.