Prenalterol
Systematic (IUPAC) name | |
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4-{[(2S)-2-hydroxy-3-(isopropylamino)propyl]oxy}phenol
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Clinical data | |
Legal status |
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Routes of administration |
Oral, IV |
Identifiers | |
CAS Number | 57526-81-5 |
ATC code | C01CA13 (WHO) |
PubChem | CID: 42396 |
IUPHAR/BPS | 537 |
ChemSpider | 38665 |
UNII | M4G34404CX |
ChEMBL | CHEMBL1160714 |
Chemical data | |
Formula | C12H19NO3 |
Molecular mass | 225.284 g/mol |
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Prenalterol is a cardiac stimulant which acts as a β1 adrenoreceptor agonist.[1]
Synthesis
Stereospecific
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.
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 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
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
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See also
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ K. A. Jaeggi, H. Schroeter, and F. Ostermayer, DE 2503968; Chem. Abstr. 84, 5322 (1976).
- ↑ corresp to U.S. Patent 3,978,041 and U.S. Patent 4,049,797 (1975, 1976, 1977, all to Ciba-Geigy).
- ↑ http://www.chemspider.com/Chemical-Structure.9312824.html
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
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