Sulfinalol

Sulfinalol
Nazivi
	IUPAC naziv 4-[1-Hidroksi-2-[4-(4-metoksifenil)butan-2-ilamino]etil]-2-metilsulfinilfenol
Identifikacija
CAS broj	66264-77-5 ;
3D model (Jmol)	interaktivna slika;
PubChem C ID	44439;
UNII	PH7O14792O ;
	SMILES CC(CCC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)S(=O)C)O; ; ; ; ; ;
Svojstva
Hemijska formula	C20H27NO4S
Molarna masa	377,50 g·mol−1
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	Reference infokutije

Sulfinalol je antagonist beta adrenergičkog receptora.^[3]

Sinteza

Metil grupa na sulfoksidu je dovoljno kisela da zameni fenolni hidroksil.

Priprema ovog kombinovanog α- i β-blokatora, sulfinalola počinje zaštitom fenolnog hidroksila kao njegovog benzoatnog estra. Bromiranje praćeno kondenzacijom sa 4-(4-metoksifenil)butan-2-aminom (ne PMA) daje aminoketon 3. Uzastopna katalitička redukcija i saponifikacija daje aminoalkohol 4. Oksidacija sulfida u sulfoksid sa reagensom kao što je metaperiodal daje sulfinalol (5).

Reference

^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
^ Sybertz, E. J.; Baum, T.; Pula, K. K.; Nelson, S.; Eynon, E.; Sabin, C. (1982). „Studies on the mechanism of the acute antihypertensive and vasodilator actions of several beta-adrenoceptor antagonists”. J. Cardiovasc. Pharmacol. 4 (5): 749—58. PMID 6182405. S2CID 34100646. doi:10.1097/00005344-198209000-00009 .
^ DE 2728641, Philion, Richard Everett, "4-Hydroxyphenylalkanolaminderivate und Verfahren zu deren Herstellung [4-Hydroxyphenylalkanolamine derivatives and processes preparation thereof]", published 1978-01-05, assigned to Sterling Drug Inc.

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[2] Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.

[3] Sybertz, E. J.; Baum, T.; Pula, K. K.; Nelson, S.; Eynon, E.; Sabin, C. (1982). „Studies on the mechanism of the acute antihypertensive and vasodilator actions of several beta-adrenoceptor antagonists”. J. Cardiovasc. Pharmacol. 4 (5): 749—58. PMID 6182405. S2CID 34100646. doi:10.1097/00005344-198209000-00009 .

[4] DE 2728641, Philion, Richard Everett, "4-Hydroxyphenylalkanolaminderivate und Verfahren zu deren Herstellung [4-Hydroxyphenylalkanolamine derivatives and processes preparation thereof]", published 1978-01-05, assigned to Sterling Drug Inc.

[1]