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Pharmacologically active derivatives of geminally di alkylated indenes and indans 2. synthesis and pharmacological screening of some 3 aminoalkyl 1 1 di alkyl indenes and 1 aminoalkylidene 3 3 di alkyl indans potent reserpine antagonists


Acta Pharmaceutica Suecica 16(3): 173-186
Pharmacologically active derivatives of geminally di alkylated indenes and indans 2. synthesis and pharmacological screening of some 3 aminoalkyl 1 1 di alkyl indenes and 1 aminoalkylidene 3 3 di alkyl indans potent reserpine antagonists
Some 3-(3-tert-aminopropyl)-1,1-dialkylindenes were prepared from the 3,3-dialkylindan-1-ones and the Grignard reagent obtained from the 3-tert-aminopropyl chloride. The Reformatsky reaction of the same indanones with ethyl bromoacetate afforded a series of 3,3-dialkylindan-1-ylideneacetic acids, which were converted into the corresponding amides. Reduction of the latter with lithium aluminium hydride afforded the 1-(2-aminoethylidene)3,3-dialkylindans. On treatment with strong acids, the amines were isomerized to the corresponding 3-(2-aminoethyl)-1,1-dialkylindenes. In screening tests [mice, guinea pigs] for CNS activity, many compounds showed potent antireserpine activity. The most potent ones are 10-30 times as active as a number of reference antidepressants, including imipramine and amitriptyline. One compound, 3'-(2-methylaminoethyl)spiro(cyclopentane-1,1'-indene) (Kabi 1847), was selected for further pharmacological evaluation.


Accession: 006098303



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