Prenalterol

Prenalterol
Clinical data
Routes of; administration	Oral, IV
ATC code	C01CA13 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 4-{[(2S)-2-hydroxy-3-(isopropylamino)propyl]oxy}phenol;
CAS Number	57526-81-5 ;
PubChem CID	42396;
IUPHAR/BPS	537;
ChemSpider	38665 ;
UNII	M4G34404CX;
ChEMBL	ChEMBL1160714 ;
CompTox Dashboard (EPA)	DTXSID8023507 ;
ECHA InfoCard	100.055.246
Chemical and physical data
Formula	C12H19NO3
Molar mass	225.288 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1ccc(O)cc1)C[C@@H](O)CNC(C)C;
	InChI InChI=1S/C12H19NO3/c1-9(2)13-7-11(15)8-16-12-5-3-10(14)4-6-12/h3-6,9,11,13-15H,7-8H2,1-2H3/t11-/m0/s1 ; Key:ADUKCCWBEDSMEB-NSHDSACASA-N ;
	(what is this?) (verify)

Prenalterol is a cardiac stimulant which acts as a β₁ adrenoreceptor agonist.^[1]

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.

Condensation of monobenzone (2) with the epoxide derived from α-D-glucofuranose^[4] affords the glycosylated derivative (3). Hydrolytic removal of the acetonide protecting groups^[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]

References

^ 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.
^ 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
^ Liu, Z; Hu, B. H.; Messersmith, P. B. (2010). "Acetonide Protection of Dopamine for the Synthesis of Highly Pure N-docosahexaenoyldopamine". Tetrahedron Letters. 51 (18): 2403–2405. doi:10.1016/j.tetlet.2010.02.089. PMC 2882309. PMID 20543896.
^ Crowther, Albert F.; Gilman, D. J.; McLoughlin, B. J.; Smith, Leslie Harold; Turner, R. W.; Wood, T. M. (1969). ".beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols". Journal of Medicinal Chemistry. 12 (4): 638–42. doi:10.1021/jm00304a018. PMID 5793156.

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

[pmid2572262-1] 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] rresp to U.S. patent 3,978,041 and U.S. patent 4,049,797 (1975, 1976, 1977, all to Ciba-Geigy).

[4] ttp://www.chemspider.com/Chemical-Structure.9312824.html

[5] Liu, Z; Hu, B. H.; Messersmith, P. B. (2010). "Acetonide Protection of Dopamine for the Synthesis of Highly Pure N-docosahexaenoyldopamine". Tetrahedron Letters. 51 (18): 2403–2405. doi:10.1016/j.tetlet.2010.02.089. PMC 2882309. PMID 20543896.

[6] Crowther, Albert F.; Gilman, D. J.; McLoughlin, B. J.; Smith, Leslie Harold; Turner, R. W.; Wood, T. M. (1969). ".beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols". Journal of Medicinal Chemistry. 12 (4): 638–42. doi:10.1021/jm00304a018. PMID 5793156.

[1]

[2]

[3]

[4]

[5]

[6]

Prenalterol

Synthesis

Stereospecific

Racemic

Further reading

See also

References