Liquid chromatographic resolution of fendiline and its analogues on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.

Abstract

Fendiline, an effective anti-anginal drug for the treatment of coronary heart diseases, and its sixteen analogues were resolved on a CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Fendiline was resolved quite well with the separation factor (α) of 1.25 and resolution (RS) of 1.55 when a mobile phase consisting of methanol-acetonitrile-trifluoroacetic acid-triethylamine at a ratio of 80/20/0.1/0.5 (v/v/v/v) was used. The comparison of the chromatographic behaviors for the resolution of fendiline and its analogues indicated that the 3,3-diphenylpropyl group bonded to the secondary amino group of fendiline is important in the chiral recognition and the difference in the steric bulkiness between the phenyl group and the methyl group at the chiral center of fendiline is also important in the chiral recognition.

• Authors: Ga Ram Lee, Myung Ho Hyun
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 19 Issue 12 Pg. 21386-97 (Dec 19 2014) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 25532838 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Acetonitriles
• Cardiovascular Agents
• Crown Ethers
• Ethylamines
• Solvents
• 18-crown-6 2,3,11,12-tetracarboxylic acid
• Trifluoroacetic Acid
• Fendiline
• triethylamine
• Methanol
• acetonitrile

Topics

• Acetonitriles (chemistry)
• Cardiovascular Agents (isolation & purification)
• Chromatography, Liquid
• Crown Ethers (chemistry)
• Ethylamines (chemistry)
• Fendiline (analogs & derivatives, isolation & purification)
• Methanol (chemistry)
• Solvents (chemistry)
• Trifluoroacetic Acid (chemistry)