2-Aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazines, a new class of antidepressants

Some 2-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazines have been shown to possess marked antidepressant activity. The 1,4-oxazines were synthesized by lithium aluminum hydride reduction of the readily available 6-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazin-3-ones. High antidepressant activity was asso...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1975-06, Vol.18 (6), p.573-577
Main Authors: Greenwood, David T, Mallion, Keith B, Todd, Alexander H, Turner, Ralph W
Format: Article
Language:English
Subjects:
Animals
Antidepressive Agents - chemical synthesis
Antidepressive Agents - pharmacology
Body Temperature - drug effects
Electroshock
Male
Mice
Motor Activity - drug effects
Oxazines - chemical synthesis
Oxazines - pharmacology
Reserpine - antagonists & inhibitors
Seizures - prevention & control
Structure-Activity Relationship
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Summary:Some 2-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazines have been shown to possess marked antidepressant activity. The 1,4-oxazines were synthesized by lithium aluminum hydride reduction of the readily available 6-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazin-3-ones. High antidepressant activity was associated with ortho substitution of the 2-phenoxymethyl group and with 1,4-oxazines devoid of 4-substituents.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00240a009