Chemistry:Amosulalol
From HandWiki
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
- upright=2
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
- ↑ "Drugs acting on multiple receptors: β-blockers with additional properties.". Pharmacology of antihypertensive therapeutics. Handbook of Experimental Pharmacology. 93. Berlin, Heidelberg: Springer. 1990. pp. 131–226 (183). doi:10.1007/978-3-642-74209-5_5. ISBN 978-3-642-74209-5. https://archive.org/details/pharmacologyofan0093unse.
- ↑ Kazuo Imai, et al., "Phenylethanolamine derivatives", US patent 4217305, 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 hydrochloride (YM-09538). J Label Compd Radiopharm 1983, 20, 7, 803-811.
- ↑ "Amosulalol". Pharmaceutical Substances. Thieme. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0117.
 |  |
