Resolution and adrenergic activities of the optical isomers of 4‐[1‐(1‐Naphthyl)ethyl]‐1H‐imidazole

Seoung S. Hong, Karl J. Romstedt, Dennis R. Feller, Fu‐Lian ‐L Hsu, Clifford George, Thomas L. Cupps, Robert A. Lyon, Duane Miller

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Recently we synthesized a naphthalene analog of medetomidine, 4‐[1‐(1‐naphthyl)ethyl]‐1H‐imidazole hydrochloride (1), and found it to be highly potent in adrenergic systems. The separation of optical isomers of this naphthalene analog was achieved by using the isomers of tartaric acid. The optical purities of the isomers were determined by HPLC using a chiral column. Using X‐ray analysis the (+)‐isomer was determined to have the S absolute configuration. It has been reported that the (+)‐isomer of medetomidine (2) is the most potent enantiomer on α2‐adrenergic receptors. There were both qualitative and quantitative differences in biological activities of the optical isomers of 1 in α1‐ and α2‐adrenergic receptor systems of guinea pig ileum and human platelets. (+)‐(S)‐1, but not (—)‐(R)‐1 was a selective agonist of α2‐mediated responses in ileum whereas (—)‐(R)‐1 was more potent than (+)‐(S)‐1 as an inhibitor of α2‐mediated platelet aggregation. © 1992 Wiley‐Liss, Inc.

Original languageEnglish (US)
Pages (from-to)432-438
Number of pages7
JournalChirality
Volume4
Issue number7
DOIs
StatePublished - Jan 1 1992
Externally publishedYes

Fingerprint

Medetomidine
Optical Rotation
Ileum
Isomers
Adrenergic Agents
Platelet Aggregation Inhibitors
Guinea Pigs
Blood Platelets
High Pressure Liquid Chromatography
X-Rays
Naphthalene
Platelets
Enantiomers
Bioactivity
naphthalene
Agglomeration
Acids

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Resolution and adrenergic activities of the optical isomers of 4‐[1‐(1‐Naphthyl)ethyl]‐1H‐imidazole. / Hong, Seoung S.; Romstedt, Karl J.; Feller, Dennis R.; Hsu, Fu‐Lian ‐L; George, Clifford; Cupps, Thomas L.; Lyon, Robert A.; Miller, Duane.

In: Chirality, Vol. 4, No. 7, 01.01.1992, p. 432-438.

Research output: Contribution to journalArticle

Hong, SS, Romstedt, KJ, Feller, DR, Hsu, FLL, George, C, Cupps, TL, Lyon, RA & Miller, D 1992, 'Resolution and adrenergic activities of the optical isomers of 4‐[1‐(1‐Naphthyl)ethyl]‐1H‐imidazole', Chirality, vol. 4, no. 7, pp. 432-438. https://doi.org/10.1002/chir.530040706
Hong, Seoung S. ; Romstedt, Karl J. ; Feller, Dennis R. ; Hsu, Fu‐Lian ‐L ; George, Clifford ; Cupps, Thomas L. ; Lyon, Robert A. ; Miller, Duane. / Resolution and adrenergic activities of the optical isomers of 4‐[1‐(1‐Naphthyl)ethyl]‐1H‐imidazole. In: Chirality. 1992 ; Vol. 4, No. 7. pp. 432-438.
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