51444-50-9Relevant academic research and scientific papers
Design and synthesis of cyclopropylamide analogues of combretastatin-A4 as novel microtubule-stabilizing agents
Chen, Huan,Li, Yongmei,Sheng, Chunquan,Lv, Zhiliang,Dong, Guoqiang,Wang, Tiantian,Liu, Jia,Zhang, Mingfeng,Li, Lingzhen,Zhang, Tao,Geng, Dongping,Niu, Chunjuan,Li, Ke
, p. 685 - 699 (2013/03/28)
A series of novel cyclopropylamide analogues of combretastatin-A4 (CA-4) were designed and synthesized. Most of them had significant in vitro antiproliferative activities, particularly for compounds 7i4, 7c4, 8a4, and 8c4. Moreover, compound 8c4 was also equally potent against paclitaxel resistant cancer cells. Interestingly, the novel cyclopropylamide analogues had different binding mechanisms from CA-4. Instead of inhibiting tubulin polymerization, these CA-4 derivatives were able to stimulate tubulin polymerization. Flow cytometry revealed that compound 8c4 arrested A549 cancer cells in the G2/M phase and resulted in cellular apoptosis. Further immunofluorescence assays revealed that compound 8c4 induced mitotic arrest in A549 cells through disrupting microtubule dynamics. In addition, compound 8c4 also effectively inhibited the tumor growth in the A549 xenograft model without causing significant loss of body weight. Compound 8c4 represents a novel class of microtubule-stabilizing agent and can be used as a promising lead for the development of new antitumor agents.
Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6- tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates
Wang, Tiantian,Liu, Jia,Zhong, Hanyu,Chen, Huan,Lv, Zhiliang,Zhang, Yikai,Zhang, Mingfeng,Geng, Dongping,Niu, Chunjuan,Li, Yongmei,Li, Ke
scheme or table, p. 3381 - 3383 (2011/06/24)
A series of ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a- carboxylates were prepared through the metal-catalyzed domino reaction of alkylidene malonates and 1,4-butynediol under a one-pot reaction condition at room temperature. Their in vitro anti-proliferative activities were subsequently evaluated in A549, QGY and HeLa cells. The majority of the compounds showed potent anti-tumor activity against HeLa cells. In particular, compound 3l was the most potent compound with IC50 value of 5.4 μM. For the first time, the X-ray structure of the anti-tumor ethyl 3-aryl-4-oxo-3,3a,4,6- tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates is determined.
Total Synthesis of (+/-)-4'-Demethyl-4-epipodophyllotoxin by Insertion-Cyclization
Kende, Andrew S.,King, Margaret Logan,Curran, Dennis P.
, p. 2826 - 2828 (2007/10/02)
The total synthesis of (+/-)-4'-O-demethyl-4-epipodophyllotoxin (3) is accomplished in 13 steps and 2.4percent overall yield from piperonal through the use of an "insertion-cyclization" reaction to form the aryltetralin ring system.
