Amosulalol

Amosulalol
Clinical data
AHFS/Drugs	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (RS)-5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide;
CAS Number	85320-68-9;
PubChemCID	2169;
ChemSpider	2084;
UNII	C69JI1BAU8;
KEGG	D07451;
ChEMBL	ChEMBL152231;
CompTox Dashboard(EPA)	DTXSID90868893;
Chemical and physical data
Formula	C18H24N2O5S
Molar mass	380.46g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C=C(C=C1)C(CNCCOC2=CC=CC=C2OC)O)S(=O)(=O)N;
	InChI InChI=1S/C18H24N2O5S/c1-13-7-8-14(11-18(13)26(19,22)23)15(21)12-20-9-10-25-17-6-4-3-5-16(17)24-2/h3-8,11,15,20-21H,9-10,12H2,1-2H3,(H2,19,22,23); Key:LVEXHFZHOIWIIP-UHFFFAOYSA-N;

Synthesis

Guaiacol(1) reacts withethylene oxideto give 2-(2-methoxyphenoxy)ethanol (2).Halogenationwiththionyl chlorideconverts the alcohol group to a chloride, (3), which is used toalkylate benzylamine(4) to give thesecondary amine(5). This forms atertiary amine(7) when combined with 5-bromoacetyl-2-methylbenzenesulfonamide (6). The reduction of thecarbonyl groupwithsodium borohydrideproduces (8) andcatalytic hydrogenationremoves thebenzyl group,yielding amosulalol.^[2]^[3]^[4]

^Sponer G, Bartsch W, Hooper RG (1990)."Drugs acting on multiple receptors: β-blockers with additional properties.".Pharmacology of antihypertensive therapeutics.Handbook of Experimental Pharmacology. Vol. 93. Berlin, Heidelberg: Springer. pp. 131–226 (183).doi:10.1007/978-3-642-74209-5_5.ISBN 978-3-642-74209-5.
^US patent 4217305,Kazuo Imai, et al., "Phenylethanolamine derivatives", issued 1980-08-12, assigned to Yamanouchi Pharmaceutical Co. Ltd.
^Arima, H.; Tamazawa, K.; Synthesis of 14C-labeled 5-[1-hydroxy-2-[2-(o-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide hydochloride (YM-09538). J Label Compd Radiopharm 1983, 20, 7, 803-811.
^"Amosulalol".Pharmaceutical Substances.Thieme.Retrieved2024-07-12.

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