2063-19-6Relevant articles and documents
Total synthesis of chiral falcarindiol analogues using BINOL-Promoted alkyne addition to aldehydes
Li, Wang,Ping-Ping, Shou,Si-Ping, Wei,Chun, Zhang,Shuang-Xun, Li,Ping-Xian, Liu,Xi, Du,Qin, Wang
, (2016)
An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1- yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps.
Synthesis, Anticancer Activity, Structure-Activity Relationship and Mechanistic Investigations of Falcarindiol Analogues
Tan, Wan-Li,Zhang, Chun,Li, Yang,Guo, Kai,Gao, Xiao-Wei,Wei, Jun,Yi, Dong,Pu, Lin,Wang, Qin
, p. 3569 - 3575 (2021)
Forty samples of optically active falcarindiol analogues are synthesized by using the easily available C2 symmetric (R)- and (S)-1,1’-binaphth-2-ol (BINOL) in combination with Ti(OiPr)4, Zn powder and EtI. Their anticancer activities on Hccc-9810, HepG2, MDA-MB-231, Hela, MG-63 and H460 cells are assayed to elucidate their structure-activity relationships. These results showed that the falcarindiol analogue (3R,8S)-2 i with the terminal double bond has the most potent anti-proliferation effect on Hccc-9810 cells with IC50 value of 0.46 μM. The falcarindiol analogue (3R,8S)-2 i can induce obvious Hccc-9810 cell apoptosis in a concentration-dependent manner by Hoechst staining and flow cytometry analysis. The proposed mechanism suggests that the falcarindiol analogue (3R,8S)-2 i increases LDH release and MDA content, and reduces the levels of SOD activity, which lead to the accumulation of oxidative stress and induce apoptosis in Hccc-9810 cells.
Synthesis and Biological Evaluation of Falcarinol-Type Analogues as Potential Calcium Channel Blockers
Li, Yang,Tan, Wan-Li,Guo, Kai,Gao, Xiao-Wei,Wei, Jun,Yi, Dong,Zhang, Chun,Wang, Qin
supporting information, p. 2138 - 2148 (2021/08/20)
A series of enantiomers of falcarinol analogues (2) were synthesized using a chiral 1,1′-binaphth-2-ol (BINOL)-based catalytic system. The neuroprotective effects of falcarinol (1a) and its analogues (2) on PC12 cells injured by sodium azide (NaN3) were investigated. The structure-function relationships and possible mechanism were studied. Pretreatment of PC12 cells with falcarinol analogues (R)-2d and (R)-2i for 1 h following addition of NaN3 and culture in a CO2 incubator for 24 h resulted in significant elevation of cell viability, as determined by a CCK-8 assay and Hoechst staining, with reduction of LDH release and MDA content, increase of SOD activity, and decrease of ROS stress, when compared with the activity of natural falcarinol (1a). These observations indicated that the falcarinol analogues (R)-2d and (R)-2i can protect PC12 cells against NaN3-induced apoptosis via increasing resistance to oxidative stress. For the first time, falcarinol (1a) and its analogue (R)-2i were found to have potential L-type calcium channel-blocking activity, as recorded using a manual patch clamp technique on HEK-293 cells stably expressing hCav1.2 (α1C/β2a/α2δ1). These findings suggest that the mechanism of the L-type calcium channel-blocking activity of falcarinol (1a) and its analogue (R)-2i might be involved in neuroprotection by falcarinol-type analogues by inhibiting calcium overload in the upstream of the signaling pathway.
Chiral falcarinol analog, synthesis method and application thereof
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Paragraph 0062; 0063; 0064, (2019/02/04)
The present invention relates to a chiral falcarinol analog, a synthesis method and application thereof. The chiral falcarinol analog has a structural formula I as shown below. Diastereoselective addition is performed on aldehyde of a terminal 1,3-diyne c
