Synthetic Studies on the Initially Proposed Structure of Protoaculeine B: Discovery of Neuronally Active Heterotricyclic Amino Acids
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(2022)
摘要
Herein, we report our results on the synthetic studies of the originally proposed structure of protoaculeine B, isolated from a marine sponge. Starting from tryptophan, two candidates of the suitably protected heterotricyclic subunits were stereoselectively synthesized over 8 and 16 steps, respectively. Furthermore, two diastereomeric heterotricyclic amino acids, finally synthesized, were found to be neuroactive: the (9S*,11S*)-isomer with natural-type configuration was hyperactive, whereas diastereomeric (9S*,11R*)-isomer was hypoactive upon mice intracerebroventricular injection.
更多查看译文
关键词
Aculeine, Amino acid, Enamide, Neuronal activity, Tryptophan
AI 理解论文
溯源树
样例
生成溯源树,研究论文发展脉络
Chat Paper
正在生成论文摘要