Ermili A, Balbi A, Roma G
Farmaco Sci. 1976 Sep;31(9):627-48.
The 2-dialkylamino-4-oxo-4H-naphtho [1,2-b]pyrans are obtained by the reaction of N,N-dialkylethoxycarbonylacetamides with alpha-naphthol and with substituted alpha-naphthols. The products on treatment with formaldehyde and morpholine or piperidine or N-methylpiperazine are transformed into the 2-dialkylamino-3-dialkylaminomethyl-4-oxo-4H-naphtho [1,2-b]pyrans. Pharmacological investigation has shown that 2-dimethylamino (K 12164), 2-(N-ethyl, N-methyl)amino- (K 12087) and 2-diethylamino-4-oxox-4H-naphtho [1,2-b]pyran (K 12165) show clear neurotropic activity of the neuroleptic type whereas compounds of the isomeric series, 1H-naphtho-[2,1-b]pyrans, studied previously (1), show anticonvulsive and sedative activity. This difference in pharmacological activity has prompted a more complete comparative examination of the activity of the two series of compounds. Study of antagonism to the effects of reserpine by both 4H-naphtho [1,2-b]pyrans and 1H-naphtho [2,1-b]pyrans has shown that in the latter series the 1-oxo-3-dimethylamino- (K 8291), the 1-oxo-3-(N-ethyl, N-methyl)amino- (K 8409) and the 1-oxo-3-diethylamino-1H-naphtho [2,1-b]-pyran (K 8292) have marked neurotropic activity of the antidepressive type.
2-二烷基氨基-4-氧代-4H-萘并[1,2-b]吡喃是通过N,N-二烷基乙氧羰基乙酰胺与α-萘酚以及取代的α-萘酚反应制得的。用甲醛和吗啉或哌啶或N-甲基哌嗪处理这些产物后，它们会转化为2-二烷基氨基-3-二烷基氨基甲基-4-氧代-4H-萘并[1,2-b]吡喃。药理学研究表明，2-二甲氨基（K 12164）、2-（N-乙基，N-甲基）氨基-（K 12087）和2-二乙氨基-4-氧代-4H-萘并[1,2-b]吡喃（K 12165）表现出明显的抗精神病类型的亲神经活性，而先前研究的（1）异构体系列1H-萘并-[2,1-b]吡喃化合物则表现出抗惊厥和镇静活性。这种药理活性的差异促使对这两个系列化合物的活性进行更全面的比较研究。对4H-萘并[1,2-b]吡喃和1H-萘并[2,1-b]吡喃对利血平作用的拮抗作用研究表明，在后一系列中，1-氧代-3-二甲氨基-（K 8291）、1-氧代-3-（N-乙基，N-甲基）氨基-（K 8409）和1-氧代-3-二乙氨基-1H-萘并[2,1-b]吡喃（K 8292）具有明显的抗抑郁类型的亲神经活性。
