Prenalterol
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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.[1][2][3][4][5] It has selectivity for the β1-adrenergic receptor.[1][2][3][4] Its partial agonist activity or intrinsic sympathomimetic activity is about 60%.[6] It is said to have much greater impact on myocardial contractility than on heart rate.[4] The drug has been marketed in Denmark, Norway, and Sweden.[2]
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.[7][8]
Condensation of monobenzone (2) with the epoxide derived from α-D-glucofuranose[9] affords the glycosylated derivative (3). Hydrolytic removal of the acetonide protecting groups[10] 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.[11][12][13][14][15]
See also
References
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- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Jaeggi KA, Schröter H, Ostermayer F, "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]", published Script error: No such module "auto date formatter"., assigned to Ciba-Geigy AGScript error: No such module "Check for unknown parameters". Chem. Abstr. 84, 5322 (1976).
- ↑ corresp to U.S. patent 3978041 and U.S. patent 4049797 (1975, 1976, 1977, all to Ciba-Geigy)
- ↑ Script error: No such module "citation/CS1".
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- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make linkScript error: No such module "Check for unknown parameters". H. Köppe et al.
- ↑ U.S. patent 3637852 (1965, 1972 both to Boehringer Ingelheim)
- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make linkScript error: No such module "Check for unknown parameters". A. F. Crowther, L. H. Smith
- ↑ U.S. patent 3501769 (1965, 1970 both to ICI)
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Further reading
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