Novel kaurane ditepene monoamides were synthesized in good yields directly from kaurenoic ( 1) and grandiflorenic ( 2) acids and unprotected symmetrical diamines, using a modified protocol for monoacylation. Amides from 1 and 2 and monoamines were also obtained and tested against seed germination and growth of radicle and shoot of Lactuca sativa (lettuce), at 10 (-3), 10 (-5), and 10 (-7) M. Amides from symmetrical diamines showed significant inhibitory activity at higher concentrations.
Alzheimer's disease is an irreversible, degenerative and age-related disease which is growing more and more with the increase in life expectancy. Kaurane diterpenes are a class of natural products available in large amounts in nature and isolated from plants grown worldwide. In the present work¸ twenty-seven kaurane diterpenes of natural origin and some readily available derivatives were assayed for acetylcholinesterase inhibition and the structure-activity relationship was analyzed. The kaurenoic acid derivatives screened showed to be promising inhibitors of AChE, which could provide new leads for drugs to fight Alzheimer's disease symptoms. Among them, eleven compounds showed activities comparable or higher than the positive control galantamine. Existence of an allylic hydroxyl group showed to be an important structural feature for AChE inhibition. In addition, presence of free hydroxyl groups at C-17 and C-19, furnished a diol especially active, able to completely inhibit AChE.
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