3,4-Methylenedioxyphenyl-, isopropylidenedioxyphenyl-, and benzyl-substituted chiral 2-aminosuccinimides and 3-aminopyrrolidines. Stereoselective investigations of potential anti-parkinsonian, antipsychotic, and anticonvulsant activities
| Autor: | Wayne L. Cook, Tribhuwan K. Gupta, Minatelli John Adrian, Donald T. Witiak, Babu R. Vishnuvajjala, Michael C. Gerald |
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| Rok vydání: | 1977 |
| Předmět: |
Male
Pyrrolidines Stereochemistry Hydrochloride medicine.medical_treatment Succinimides Methylenedioxy Antiparkinson Agents chemistry.chemical_compound Mice Succinimide Seizures Drug Discovery medicine Animals Humans Antipsychotic Postural Balance Biological activity Stereoisomerism Rats Anticonvulsant chemistry Molecular Medicine Stereoselectivity Anticonvulsants Enantiomer Stereotyped Behavior Antipsychotic Agents |
| Zdroj: | Journal of medicinal chemistry. 20(6) |
| ISSN: | 0022-2623 |
| Popis: | The chiral title compounds 2--11 were assessed for their potential anti-Parkinsonian, antipsychotic, and anticonvulsant properties. The most striking differences in the biological activity of enantiomeric pairs were noted for D-(R)-2-amino-N-(3,4-methylenedioxyphenyl)succinimide hydrochloride (2) vs. L-(S)-3 and D-(R)-2-amino-N-(3,4-isopropylidenedioxyphenyl)succinimide (4) vs. L-(S)-5. D-(R)-2-partially attenuated amphetamine-induced stereotyped behavior, whereas D-(R)-4 antagonized oxotremorine-induced tremors. Their respective enantiomorphs were inactive in these tests. No differences in anticonvulsant potency of enantiomeric pairs were observed. The stereoselective actions of D-(R)-2 and 4 were rationalized on the basis of the presence or absence of gem-dimethyl functions in isopropylidenedioxy vs. methylenedioxy groups; the data seem to indicate that these methyl groups influence selective receptor site interaction in the D-(R) series. |
| Databáze: | OpenAIRE |
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