22525-95-7

Basic information

• Product Name: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon
• Synonyms: Einecs 245-052-7;2-(2,3-Epoxypropoxy)-3-phenylpropylophenone;Propafenone IMp. C (EP);Propafenone IMpurity C (EP/BP/USP);1-[2-(oxiran-2-ylMethoxy)phenyl]-3-phenylpropan-1-one;Propafenone EP Impurity C;2'-(2,3-EPOXYPROPOXY)-3-PHENYLPROPLOPHENONE;2'-(oxiranylmethoxy)-3-phenylpropiophenone
• CAS NO: 22525-95-7
• Molecular Formula: C₁₈H₁₈O₃
• Molecular Weight: 282.33
• EINECS: 245-052-7
• Product Categories: Aromatics;Heterocycles
• Mol File: 22525-95-7.mol

Chemical Properties

• Melting Point: 56-58°C
• Boiling Point: 452.8 °C at 760 mmHg
• Flash Point: 219.6 °C
• Appearance: Pale-yellow solid
• Density: 1.164 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate, DMSO (Slightly)
• CAS DataBase Reference: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon(22525-95-7)
• EPA Substance Registry System: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon(22525-95-7)

Safety Data

• Hazardous Substances Data: 22525-95-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-(Oxiranylmethoxy)-3-phenylpropiophenon is used as an impurity in the synthesis of propafenone (P757500) for the pharmaceutical industry. Its presence is significant as it can impact the quality and efficacy of the final drug product. Ensuring the removal or reduction of this impurity is crucial for maintaining the safety and effectiveness of propafenone as a medication for heart rhythm disorders.
Additionally, understanding the properties and behavior of this impurity can aid in the development of improved synthesis methods or purification techniques, which could potentially enhance the overall quality of propafenone and other related pharmaceutical compounds.

Upstream product

• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 
• 106-89-8 epichlorohydrin 
• 118-93-4 o-hydroxyacetophenone 
• 100-52-7 benzaldehyde 
• 16619-51-5 2'-allyloxychalcone 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 

Downstream Products

• 91401-73-9 2-(2',3'-dihydroxy-propoxy)-ω-phenyl-propiophenone 
• 93885-34-8 1-[2-(3-Bromo-2-hydroxy-propoxy)-phenyl]-3-phenyl-propan-1-one 
• 165279-79-8 1-(2-(3-Chlor-2-hydroxy-propoxy)phenyl)-3-phenyl-1-propanon 
• 178691-47-9 1-(2-(3-benzylamino-2-hydroxypropoxy)phenyl)-3-phenyl-1-propanone 
• 165279-75-4 1-chloro-2-(3-(2-phenyl-ethyl)-2-benzofuryl)-ethane 
• 165279-82-3 2-Chloro-1-(3-phenethyl-benzofuran-2-yl)-ethanone 
• 165279-81-2 2-Chlor-1-(2,3-dihydro-3-hydroxy-3-(2-phenylethyl)benzofuran-2-yl)ethanon 
• 165279-80-1 1-Chlor-3-(2-(3-phenylpropionyl)phenyloxy)aceton 
• 183883-07-0 2-[4-(2-methoxyphenyl)-1-piperazinyl]-1-[3-(2-phenylethyl)-2-benzofuryl]ethanone 

Relevant articles and documents

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Preparation methods of propafenone hydrochloride and intermediate 2'-hydroxydihydrochalcone thereof

The invention discloses preparation methods of propafenone hydrochloride and an intermediate 2'-hydroxydihydrochalcone thereof. 2-phenyl-benzothiazoline is adopted as a reducing agent to construct a reduction system, carbon-carbon double bonds are reduced, double bonds in a substrate can be efficiently and selectively reduced, and the problem that the propafenone hydrochloride key intermediate 2'-hydroxydihydrochalcone is synthesized by using hydrogen is avoided. The used reducing agent is simple and easily available, and the preparation methods have the advantages of low requirements on reaction equipment and operation, suitableness for industrial production, no hydrogen and noble metals, safety and environmental friendliness.

Optimization of propafenone analogues as antimalarial leads

Propafenone, a class Ic antiarrythmic drug, inhibits growth of cultured Plasmodium falciparum. While the drug's potency is significant, further development of propafenone as an antimalarial would require divorcing the antimalarial and cardiac activities as well as improving the pharmacokinetic profile of the drug. A small array of propafenone analogues was designed and synthesized to address the cardiac ion channel and PK liabilities. Testing of this array revealed potent inhibitors of the 3D7 (drug sensitive) and K1 (drug resistant) strains of P. falciparum that possessed significantly reduced ion channel effects and improved metabolic stability. Propafenone analogues are unusual among antimalarial leads in that they are more potent against the multidrug resistant K1 strain of P. falciparum compared to the 3D7 strain.

The hERG potassium channel and drug trapping: Insight from docking studies with propafenone derivatives

The inner cavity of the hERG potassium ion channel can accommodate large, structurally diverse compounds that can be trapped in the channel by closure of the activation gate. A small set of propafenone derivatives was synthesized, and both use-dependency and recovery from block were tested in order to gain insight into the behavior of these compounds with respect to trapping and non-trapping. Ligand-protein docking into homology models of the closed and open state of the hERG channel provides the first evidence for the molecular basis of drug trapping.

Structure-activity relationship studies on benzofuran analogs of propafenone-type modulators of tumor cell multidrug resistance

A series of benzofurylethanolamine analogs of propafenone (1a) have been prepared and evaluated for multidrug resistance-reversing activity in two in vitro assay systems. As for propafenones, an excellent correlation of biological data with calculated lipophilicity values was found for benzofurans, whereby the latter generally had lower activity/lipophilicity ratios. Almost identical slopes of the regression lines were obtained for both propafenones and benzofurans. Multiple linear regression analysis of the complete data set yielded an equation with excellent predictive power (r2(cross-valid) = 0.968). Interaction measurements with artificial membranes indicated that the differences in activity between these two series of compounds are not due to differences in the interaction pattern with biological membranes.

Synthesis, Pharmacologic Activity, and Structure-Activity Relationships of a Series of Propafenone-Related Modulators of Multidrug Resistance

A series of propanolamines have been prepared and evaluated for multidrug resistance-reverting activity in a human tumor cell model.Structure-activity relationship studies indicate that the phenylpropiophenone moiety as well as the substitution pattern at the nitrogen atom is crucial for activity of the compounds.Incorporation of the ether oxygen into a benzofuran substructure, which renders the compound an arylethanolamine, decreased biologic activity.Highest activity could be observed with the arylpiparazines 4f-h, which not only completely restored daunomycin sensitivity but also showed moderate activity in restoring etoposide toxicity.

Studies on the metabolism of propafenone. 1st comm.: Synthesis and chromatographic/mass spectrometric properties of the labelled compound and of the reference substances

The synthesis of 14C-propafenone and 2H-propafenone (propafenone: 2-(2'-hydroxy-3'-propylamino-propoxy)-ω-phenyl-propiophenone hydrochloride) and some reference compounds is described. The thin-layer chromatographic, high-performance liquid and gas chromatographic properties of the substances are described. Propafenone and the reference substances were studied by mass spectrometry and compared with each other, with respect to structural elucidation of the metabolites. The chromatographic and mass spectrometric data (key ions) enables the metabolites of propafenone to be identified in biological material.