Synthesis and anticholinergic activity of the four stereoisomers of 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide.

Abstract

The four stereoisomers of 4-(dimethylamino)-2-phenyl-(2-pyridyl)pentanamide were synthesized, and the absolute configurations were determined by X-ray crystallography. Pharmacological testing for anticholinergic activity revealed great differences in potency among 10 (2R,4R,IC50 = 0.40 microM), 11 (2S,4S,31 microM), 12 (2R,4S,170 microM), and 13 (2S,4R,0.13 microM). A new drug application for the racemate 8 (FK176, vamicamide) has been filed in Japan for the treatment of overactive detrusor syndrome.

• Authors: H Oyasu, M Nagano, A Akahane, M Tomoi, T Tada, M Matsuo
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 37 Issue 9 Pg. 1378-81 (Apr 29 1994) ISSN: 0022-2623 [Print] United States
• PMID: 8176715 (Publication Type: Journal Article)

Chemical References

• Parasympatholytics
• Pyridines
• vamicamide

Topics

• Animals
• Crystallography, X-Ray
• Guinea Pigs
• Ileum (drug effects, physiology)
• Molecular Structure
• Muscle Contraction (drug effects)
• Parasympatholytics (chemical synthesis, chemistry, pharmacology)
• Pyridines (chemical synthesis, chemistry, pharmacology)
• Stereoisomerism