Prenalterol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Prenalterol
Prenalterol.png
Systematic (IUPAC) name
4-{[(2S)-2-hydroxy-3-(isopropylamino)propyl]oxy}phenol
Clinical data
Legal status
  • (Prescription only)
Routes of
administration
Oral, IV
Identifiers
CAS Registry Number 57526-81-5 N
ATC code C01CA13
PubChem CID: 42396
IUPHAR/BPS 537
ChemSpider 38665 YesY
UNII M4G34404CX YesY
ChEMBL CHEMBL1160714 YesY
Chemical data
Formula C12H19NO3
Molecular mass 225.284 g/mol
 N (what is this?)  (verify)

Prenalterol is a cardiac stimulant which acts as a β1-adrenergic agonist.[1]

Synthesis[edit]

Stereospecific[edit]

Prenalterol interestingly exhibits adrenergic agonist acitivity 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:[2][3]

Condensation of the monobenzyl ether of phenol 1 with the epoxide derived from α-D-Glucofuranose[4] affords the glycosylated derivative (3). Hydrolytic removal of the acetonide protecting groups (cf. eg[5]) followed by cleavage of the sugar with periodate gives aldehyde (4). This is reduced the 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[edit]

Prepns of the racemic mixture: NL 6409883  corresp to H. Köppe et al., U.S. Patent 3,637,852 (1965, 1972 both to Boehringer Ingelheim); NL 301580  corresp to A. F. Crowther, L. H. Smith, U.S. Patent 3,501,769 (1965, 1970 both to ICI);[6]

Further Reading[edit]

Symposium:[7]

See also[edit]

References[edit]

  1. ^ Hadfield SE, Slee SJ, Snow HM (1989). "The cardiovascular pharmacology of xamoterol, cicloprolol, prenalterol and pindolol in the anaesthetised dog". Br J Clin Pharmacol. 28 Suppl 1 (Suppl 1): 78S–81S. doi:10.1111/j.1365-2125.1989.tb03580.x. PMC 1379883. PMID 2572262. 
  2. ^ K. A. Jaeggi, H. Schroeter, and F. Ostermayer, DE 2503968 ; Chem. Abstr. 84, 5322 (1976).
  3. ^ corresp to U.S. Patent 3,978,041 and U.S. Patent 4,049,797 (1975, 1976, 1977, all to Ciba-Geigy).
  4. ^ http://www.chemspider.com/Chemical-Structure.9312824.html
  5. ^ PMID 20543896 (PubMed)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  6. ^ doi:10.1021/jm00304a018
    This citation will be automatically completed in the next few minutes. You can jump the queue or expand by hand
  7. ^ doi:10.1111/joim.1982.211.issue-s659
    This citation will be automatically completed in the next few minutes. You can jump the queue or expand by hand