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Structure-Activity Relationship of 39 Analogs of Laetispicine with Antidepressant Properties.
- Source :
- American Journal of Chinese Medicine; 2013, Vol. 41 Issue 6, p1377-1392, 16p, 2 Black and White Photographs, 3 Charts, 4 Graphs
- Publication Year :
- 2013
-
Abstract
- The natural product Laetispicine (N-isobutyl-(3,4-methylendioxyphenyl)-2E, 4E, 9E-undecatrienoamide), was isolated from the Piper laetispicum C. DC and screened, for its antidepressant activity and antinociceptive effects. Structure-functional activities of five natural products indicated that biological activity is dependent on double bonds present within the benzene ring and a conjugated double bond located at positions 2-3 and 4-5 in the molecular structure. To further understand the structural-activity relationship of Laetispicine as a new potent and safe antidepressant, the structural-activity relationship of 39 analogs of Laetispicine were synthetized and tested in forced swimming tests in mice whilst also in protective effects against glutamate or H<subscript>2</subscript>O<subscript>2</subscript> induced apoptosis in PC12 cells. The results show that the compound 30 — N-isobutyl-11-(4-chlorophenyl) undeca-2E,4E,9E-trienamide exhibited the same activity as the parental compound Laetispicine, and furthermore, the effective dose of this compound is lower than Laetispicine. Therefore, the compound 30 might be a potentially useful therapy in the treatment of depression. For structure, the conjugated double bonds located at 2-3, 4-5 and isolated double bonds from benzene ring are necessary for the antidepressant activities no matter the different length of carbon chain; the isobutyl connected with acylamino also are necessary; and the benzodioxole moiety is replaceable, the halogen atom in phenyl ring at the para-position could enhance this kind of activity. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 0192415X
- Volume :
- 41
- Issue :
- 6
- Database :
- Complementary Index
- Journal :
- American Journal of Chinese Medicine
- Publication Type :
- Academic Journal
- Accession number :
- 91967531
- Full Text :
- https://doi.org/10.1142/S0192415X13500924