- Selective inhibitors of monoamine oxidase (MAO). 5.1,2 1-Substituted phenoxathiin inhibitors containing no nitrogen that inhibit MAO a by binding it to a hydrophobic site
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It is believed that a monoamine oxidase (MAO) inhibitor specific for MAO A, which is reversibly bound to this enzyme and displaceable by tyramine, will be an antidepressant which will not cause a rise in blood pressure when tyramine-containing foods are ingested. Some linear tricyclic compounds with a larger and a smaller group forming the central ring and with a lipophilic group ortho to the larger group (here mostly the SO2 function of phenoxathiin 10,10-dioxide) are reported to have the sought properties. Potency appears to require short length and relatively small cross section for the substituent. The 1-ethyl (13), 1-vinyl (22), 1-trifluoromethyl (27), and 1-iodo (76) phenoxathiin dioxides had the best profiles. Structure- activity relationships, syntheses, and a possible rationale for the selectivity of these compounds and related tricyclics are given. Compound 13 was selected for further development. A summary of pharmacological data for 13 is given.
- Harfenist, Morton,McGee, Daniel P.C.,Reeves, Mark D.,White, Helen L.
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p. 2118 - 2125
(2007/10/03)
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- PHARMACOLOGICALLY ACTIVE COMPOUND AND USE
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1-Ethylphenoxathiin 10,10-dioside (I) inhibits monoamine oxidase-A and is useful in the treatment of disorders such as depression.
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