697266-01-6Relevant academic research and scientific papers
Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure–activity relationship of its derivatives
Cao, Li,Lin, Jiahao,Sun, Zhonghao,Tian, Yu,Xu, Chengfang,Xu, Xudong,Yang, Shuxian,Yi, Fan
, (2021/09/20)
Natural products–polyoxygenated cyclohexenes exhibited potent anti-tumor activity, such as zeylenone, which is a natural product isolated from Uvaria grandiflora Roxb. This article will attempt to establish a gram-scale synthesis method of (+)-zeylenone and explain the structure–activity relationship of this kind of compound. Total synthesis of (+)-zeylenone was completed in 13 steps with quinic acid as the starting material in 9.8% overall yield. The highlight of the route was the control of the three carbon's chirality by single step dihydroxylation. In addition, different kinds of derivatives were designed and synthesized. Cell Counting Kit-8 (CCK8) assay was used for evaluating antitumor activity against three human cancer cell lines. The structure–activity relationship suggested that compounds with both absolute configurations exhibited tumor-suppressive effects. Moreover, hydroxyls at the C-1/C-2 position were crucial to the activity, and the esterification of large groups at C-1 hydroxyl eliminated the activity. Hydroxyl at the C-3 position was also important as proper ester substituent could increase the potency.
Synthesis of (+)-zeylenone from shikimic acid
Liu, An,Liu, Zhan Zhu,Zou, Zhong Mei,Chen, Shi Zhi,Xu, Li Zhen,Yang, Shi Lin
, p. 3689 - 3694 (2007/10/03)
Starting from shikimic acid, the total synthesis of zeylenone was studied. The product was proved to be the (+)antipode of zeylenone through analysis and comparison of their respective spectra (including NMR, MS, IR and CD) and optical data. The absolute
