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Prenalterol

Chemical compound

Prenalterol

Chemical compound

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Prenalterol, sold under the brand name Hyprenan, is a sympathomimetic agent and cardiac stimulant which acts as a β1-adrenergic receptor partial agonist and is used in the treatment of heart failure. It has selectivity for the β1-adrenergic receptor. Its partial agonist activity or intrinsic sympathomimetic activity is about 60%. It is said to have much greater impact on myocardial contractility than on heart rate. The drug has been marketed in Denmark, Norway, and Sweden.

Chemistry

Synthesis

Stereospecific

Prenalterol exhibits adrenergic agonist activity in spite of an interposed oxymethylene group. The stereospecific synthesis devised for this molecule relies on the fact that the side chain is very similar in oxidation state to that of a sugar.

Prenalterol synthesis

Condensation of monobenzone (2) with the epoxide derived from α-D-glucofuranose affords the glycosylated derivative (3). Hydrolytic removal of the acetonide protecting groups followed by cleavage of the sugar with periodate gives aldehyde (4). This is reduced to the glycol by means of NaBH4 and the terminal alcohol is converted to the mesylate (5). Displacement of the leaving group with isopropylamine followed by hydrogenolytic removal of the O-benzyl ether affords the β1-adrenergic selective adrenergic agonist prenalterol (6).

Racemic

Several preparations of the racemic mixture have been reported.

References

References

  1. (2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer US.
  2. Schweizerischer Apotheker-Verein. (2000). "Index Nominum 2000: International Drug Directory". Medpharm Scientific Publishers.
  3. (2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Netherlands.
  4. (June 1982). "Prenalterol--a new cardioselective inotropic agent". J Clin Hosp Pharm.
  5. (1989). "The cardiovascular pharmacology of xamoterol, cicloprolol, prenalterol and pindolol in the anaesthetised dog". British Journal of Clinical Pharmacology.
  6. (January 1985). "Prenalterol: a partial beta 1-adrenoceptor agonist or a beta-blocker with intrinsic activity?". Int J Clin Pharmacol Ther Toxicol.
  7. "Optisch aktive Derivate des 1-Phenoxy-2-hydroxy-3-aminopropan und Verfahren zu ihrer Herstellung [Optically active derivatives of 1-phenoxy-2-hydroxy-3-aminopropane and the process for their production]".
  8. corresp to {{US patent. 3978041 and {{US patent. 4049797 (1975, 1976, 1977, all to [[Ciba-Geigy]])
  9. "Α-D-Glucofuranose | C6H12O6". ChemSpider.
  10. (May 2010). "Acetonide Protection of Dopamine for the Synthesis of Highly Pure N-docosahexaenoyldopamine". Tetrahedron Letters.
  11. {{Cite patent
  12. {{US patent. 3637852 (1965, 1972 both to [[Boehringer Ingelheim]])
  13. {{Cite patent
  14. {{US patent. 3501769 (1965, 1970 both to [[Imperial Chemical Industries. ICI]])
  15. (July 1969). "Beta-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols". Journal of Medicinal Chemistry.
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secondary-amines beta1-adrenergic-agonists cardiac-stimulants inotropic-agents phenol-ethers 4-hydroxyphenyl-compounds secondary-alcohols sympathomimetics
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