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(Top) 1 Synthesis 1.1 Stereospecific 1.2 Racemic 2 See also 3 References 4 Further reading

Prenalterol

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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^N
PubChem CID	42396
IUPHAR/BPS	537
ChemSpider	38665^Y
UNII	M4G34404CX
ChEMBL	ChEMBL1160714^Y
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^Y Key:ADUKCCWBEDSMEB-NSHDSACASA-N^Y
^NY (what is this?) (verify)

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

Synthesis[edit]

Stereospecific[edit]

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:^[2]^[3]

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[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]

References[edit]

^ Hadfield SE, Slee SJ, Snow HM (1989). "The cardiovascular pharmacology of xamoterol, cicloprolol, prenalterol and pindolol in the anaesthetised dog". British Journal of Clinical Pharmacology. 28 (Suppl 1): 78S–81S. doi:10.1111/j.1365-2125.1989.tb03580.x. PMC 1379883. PMID 2572262.

^ DE 2503968, 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 1975-08-14, assigned to Ciba-Geigy AG 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).

^ "Α-D-Glucofuranose | C6H12O6". ChemSpider.

^ Liu Z, Hu BH, Messersmith PB (May 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 AF, Gilman DJ, McLoughlin BJ, Smith LH, Turner RW, Wood TM (July 1969). "Beta-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols". Journal of Medicinal Chemistry. 12 (4): 638–642. doi:10.1021/jm00304a018. PMID 5793156.