107381-32-8

Basic information

• Product Name: (S)-Propafenone
• Synonyms: (-)-(S)-Propafenone;(S)-Propafenone;1-Propanone, 1-[2-[(2S)-2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl- (9CI);1-Propanone, 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-, (S)-;(-)-Propafenon;1-[2-[(S)-2-Hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone;2'-[(2S)-2-Hydroxy-3-(propylamino)propoxy]-β-phenylpropiophenone;1-[2-[(2S)-2-hydroxy-3-(propylaMino)propoxy]phenyl]-3-phenyl-
• CAS NO: 107381-32-8
• Molecular Formula: C₂₁H₂₇NO₃
• Molecular Weight: 341.448
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 107381-32-8.mol

Chemical Properties

• Boiling Point: 519.6°Cat760mmHg
• Flash Point: 268°C
• Appearance: /
• Density: 1.096g/cm³
• Vapor Pressure: 1.27E-11mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (S)-Propafenone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Propafenone(107381-32-8)
• EPA Substance Registry System: (S)-Propafenone(107381-32-8)

Safety Data

• Hazardous Substances Data: 107381-32-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3/t18-/m0/s1

Upstream product

• 74748-75-7 (S)-(+)-<<(trifluoromethanesulfonyl)oxy>methyl>oxirane 
• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 
• 107300-59-4 propafenone 

Downstream Products

• 107325-60-0 1-{(S)-2-Hydroxy-3-[2-(3-phenyl-propionyl)-phenoxy]-propyl}-3-((R)-1-phenyl-ethyl)-1-propyl-urea 

Relevant articles and documents

Colistin sulfate chiral stationary phase for the enantioselective separation of pharmaceuticals using organic polymer monolithic capillary chromatography ?

A new functionalized polymer monolithic capillary with a macrocyclic antibiotic, namely colistin sulfate, as chiral selector was prepared via the copolymerization of binary monomer mixtures consisting of glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDMA) in porogenic solvents namely 1-propanol and 1,4-butanediol, in the presence of azobisiso-butyronitrile (AIBN) as initiator and colistin sulfate. The prepared capillaries were investigated for the enantioselective nano-LC separation of a group of racemic pharmaceuticals, namely, α- and β-blockers, anti-inflammatory drugs, antifungal drugs, norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, antihistaminics, anticancer drugs, and antiarrhythmic drugs. Acceptable separation was achieved for many drugs using reversed phase chromatographic conditions with no separation achieved under normal phase conditions. Colistin sulfate appears to be useful addition to the available macrocyclic antibiotic chiral phases used in liquid chromatography.

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.

Therapeutic agents containing enantiomers of propafenone

Therapeutic agents containing enantiomers of propafenone, the preparation of the said agents and their use for certain groups of patients.

Optical Resolution of Propafenone and Diprafenone, Configuration of Propafenone Enantiomers

The chiral antiarrhythmic drugs propafenone (rac-1) and diprafenone (rac-3) were resolved by fractional crystallization of the diastereoisomeric salts with optically active di-O,O'-p-toluoyltartaric acid and tartaric acid, respectively.Derivatization with (+)-1-phenylethyl isocyanate and analytical separation of the diastereoisomers 2 and 4 by HPLC confirmed the optical purity of the enantiomers.CD spectra of (+)- and (-)-propafenone as copper complexes established the absolute configuration: (-)-1 is R-, (+)-1 S-configurated.