Amosulalol
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Amosulalol (INN) is an antihypertensive drug. It has much higher affinity for α1-adrenergic receptors than for β-adrenergic receptors.[1] It is not approved for use in the United States.
Synthesis
Guaiacol (1) reacts with ethylene oxide to give 2-(2-methoxyphenoxy)ethanol (2). Halogenation with thionyl chloride converts the alcohol group to a chloride, (3), which is used to alkylate benzylamine (4) to give the secondary amine (5). This forms a tertiary amine (7) when combined with 5-bromoacetyl-2-methylbenzenesulfonamide (6). The reduction of the carbonyl group with sodium borohydride produces (8) and catalytic hydrogenation removes the benzyl group, yielding amosulalol.[2][3][4]
References
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- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Kazuo Imai, et al., "Phenylethanolamine derivatives", issued Script error: No such module "auto date formatter"., assigned to Yamanouchi Pharmaceutical Co. Ltd.Script error: No such module "Check for unknown parameters".
- ↑ Arima, H.; Tamazawa, K.; Synthesis of 14C-labeled 5-[1-hydroxy-2-[2-(o-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide hydrochloride (YM-09538). J Label Compd Radiopharm 1983, 20, 7, 803-811.
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