150726-89-9

Basic information

• Product Name: Dimethyl 2-(2-methoxyphenoxy)malonate
• Synonyms: DIMETHYL (2-METHOXYPHENOXY)MALONATE;Dimethyl-2-(2-methoxyphenoxy)malonate;(2-Methoxyphenoxy)-propanedioic Acid Dimethyl Ester;Dimethyl (o-Methoxyphenoxy)malonate;2-(2-Methoxyphenoxy)malonic acid dimethyl ester;1,3-diMethyl 2-(2-Methoxyphenoxy)propanedioate;2-MethoxyphenoxyMalonate
• CAS NO: 150726-89-9
• Molecular Formula: C₁₂H₁₄O₆
• Molecular Weight: 254.24
• EINECS: 604-747-9
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 150726-89-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 320.47 °C at 760 mmHg
• Flash Point: 138.381 °C
• Appearance: White solid
• Density: 1.206 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane, Methanol
• PKA: 12.17±0.59(Predicted)
• CAS DataBase Reference: Dimethyl 2-(2-methoxyphenoxy)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 2-(2-methoxyphenoxy)malonate(150726-89-9)
• EPA Substance Registry System: Dimethyl 2-(2-methoxyphenoxy)malonate(150726-89-9)

Safety Data

• Hazardous Substances Data: 150726-89-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Dimethyl 2-Methoxyphenoxymalonate (cas# 150726-89-9) is a compound useful in organic synthesis.

InChI:InChI=1/C12H14O6/c1-15-8-6-4-5-7-9(8)18-10(11(13)16-2)12(14)17-3/h4-7,10H,1-3H3

Upstream product

• 28868-76-0 2-chlorodimethylmalonate 
• 90-05-1 2-methoxy-phenol 
• 38768-62-6 methyl (2-methoxyphenoxy) ethanoate 
• 616-38-6 carbonic acid dimethyl ester 
• 1878-85-9 (2-methoxyphenoxy)acetic acid 

Downstream Products

• 167403-76-1 5-(2-methoxy-phenoxy)-2-(morpholin-4-yl)-4,6(1H,5H)-pyrimidinedione 
• 184779-24-6 4,6-dihydroxy-5-(2-methoxyphenoxy)-2-methylthiopyrimidine 
• 441797-61-1 C₂₂H₁₉ClN₆O₄S 
• 441797-50-8 C₂₃H₂₀ClN₅O₄S 
• 441797-53-1 C₂₁H₂₁ClN₄O₄S 
• 441797-63-3 C₁₈H₁₇ClN₄O₄S 
• 441797-09-7 N-(6-(2-hydroxyethoxy)-2-methylsulfanyl-5-(2-methoxyphenoxy)pyrimidin-4-yl)-N'-benzylsulfamide 
• 441797-10-0 N-(6-(2-hydroxyethoxy)-2-methylsulfonyl-5-(2-methoxyphenoxy)pyrimidin-4-yl)-N'-benzylsulfamide 
• 1393813-68-7 N-(6-(2-hydroxyethoxy)-2-(2-methoxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl)-N'-benzylsulfamide 
• 473537-04-1 4,6-dichloro-5-(2-methoxy-phenoxy)-2-pyrazin-2-yl-pyrimidine 
• 150727-72-3 4,6-dichloro-5-(o-methoxyphenoxy)-2-(pyridin-4-yl)-pyrimidine 
• 167403-77-2 4,6-dichloro-5-(2-methoxy-phenoxy)-2-(morpholin-4-yl)pyrimidine 
• 329924-27-8 4,6-dichloro-5-(2-methoxyphenoxy)-2-cyclopropyl-pyrimidine 
• 184779-19-9 2,4,6-trichloro-5-(2-methoxyphenoxy)pyrimidine 

Relevant articles and documents

Metabolism study and biological evaluation of bosentan derivatives

Bosentan, the first-in-class drug used in treatment of pulmonary arterial hypertension, is principally metabolized by the cytochromes P450, and it is responsible for cytochromes induction and drug-drug interaction events with moderate to severe consequences. A strategy to reduce drug-drug interactions consists of increasing the metabolic stability of the perpetrator, and fluorinated analogues are often designed to block the major sites of metabolism. In this paper bosentan analogues were synthesized, and their metabolism and biological activity were evaluated. All synthesized compounds showed an improved metabolic stability towards CYP2C9, with one maintaining a moderate antagonist effect towards the ETA receptor.

The discovery of N -[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy] ethoxy]-4-pyrimidinyl]- N ′-propylsulfamide (macitentan), an orally active, potent dual endothelin receptor antagonist

Starting from the structure of bosentan (1), we embarked on a medicinal chemistry program aiming at the identification of novel potent dual endothelin receptor antagonists with high oral efficacy. This led to the discovery of a novel series of alkyl sulfamide substituted pyrimidines. Among these, compound 17 (macitentan, ACT-064992) emerged as particularly interesting as it is a potent inhibitor of ETA with significant affinity for the ET B receptor and shows excellent pharmacokinetic properties and high in vivo efficacy in hypertensive Dahl salt-sensitive rats. Compound 17 successfully completed a long-term phase III clinical trial for pulmonary arterial hypertension.

Arylalkane-sulfonamides having endothelin-antagonist activity

The invention relates to novel aryl-alkane-sulfonamides and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.