Typha

by | Mar 22, 2018 | Typha

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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

  1. ^ 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.
  2. ^ US patent 4217305, Kazuo Imai, et al., "Phenylethanolamine derivatives", issued 1980-08-12, assigned to Yamanouchi Pharmaceutical Co. Ltd. 
  3. ^ 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.
  4. ^ "Amosulalol". Pharmaceutical Substances. Thieme. Retrieved 2024-07-12.



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