Total Synthesis, Structural Elucidation, and Structure–Cytotoxic Activity Relationship of (−)-Gummiferol

2013 ◽  
Vol 78 (6) ◽  
pp. 2443-2454 ◽  
Author(s):  
Hiroyoshi Takamura ◽  
Hiroko Wada ◽  
Nan Lu ◽  
Osamu Ohno ◽  
Kiyotake Suenaga ◽  
...  
2008 ◽  
Vol 61 (7) ◽  
pp. 531 ◽  
Author(s):  
Qiang Zhou ◽  
Jing Hou ◽  
Huamin Li ◽  
Li Cui ◽  
Han Jia ◽  
...  

Designed as a new series of molecules that contain the quinoline substructure, several 11H-indolo[3.2-c]quinoline derivatives were synthesized and subjected to biological evaluation. Several compounds were found to exhibit cytotoxic activity against the growth of colon (HTC-8), liver (BEL-7402), gastric (BCG-823), pulmonary gland (A549), and ovary (A2780) cancer cell lines. The structure–activity relationship of these compounds is discussed.


2013 ◽  
Vol 23 (14) ◽  
pp. 4102-4106 ◽  
Author(s):  
Bogumiła Kupcewicz ◽  
Grażyna Balcerowska-Czerniak ◽  
Magdalena Małecka ◽  
Piotr Paneth ◽  
Urszula Krajewska ◽  
...  

Author(s):  
Zhonghao Sun ◽  
Shuxian Yang ◽  
Chengfang Xu ◽  
Guoxu Ma ◽  
Li Cao ◽  
...  

(-)-Zeylenone is a promising cytotoxic agent,which is a natural product isolated from Uvaria grandiflora Roxb. Though substantial antitumor mechanism has been researched , little has focused on its enantiomer (+)-Zeylenone.This article will try to find 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 starting material in 8.8% overall yield. The highlight of the route was the control of the three carbon’s chirality by clever use of single step dihydroxylation under the direction of the key C-3 chirality. In addition, zeylenone derivatives were designed and synthesized and their antitumor activity were evaluated against three human cancer cell lines using the CCK8 assay. Structure-activity relationship suggested compounds with both two absolute configurations exhibited good activity. Besides, hydroxyls at C-1/2 position were crucial for the activity and esterification of C-1 hydroxyl with large groups made the activity disappeared. Hydroxyl at C-3 position was also important as proper ester substituent could increase the potency.


2014 ◽  
Vol 62 (23) ◽  
pp. 5305-5315 ◽  
Author(s):  
Tuti Wukirsari ◽  
Hisashi Nishiwaki ◽  
Kosuke Nishi ◽  
Takuya Sugahara ◽  
Koichi Akiyama ◽  
...  

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