26357-07-3Relevant articles and documents
Design, synthesis and antiproliferative effect of 17β-amide derivatives of 2-methoxyestradiol and their studies on pharmacokinetics
Shi, Xiufang,Wang, Zhihao,Xu, Feng,Lu, Xiang,Yao, Haifeng,Wu, Dandan,Sun, Shuaijun,Nie, Ruifang,Gao, Shuo,Li, Panpan,Xia, Liwen,Zhang, Zhenzhong,Wang, Cong
, p. 6 - 14 (2017/10/27)
A series of 17β-amide-2-methoxyestradiol compounds were synthesized with an aim to enhance the antiproliferative effect of 2-methoxyestradiol. The antiproliferative activity of 2-methoxyestradiol analogs against human cancer cells was investigated. 2-methoxy-3-benzyloxy-17β-chloroacetamide-1,3,5(10)-triene (5e) and 2-methoxy-3-hydroxy-17β-butyramide-1,3,5(10)-triene (6c) had comparable or better antitumor activity than 2-methoxyestradiol. The elimination half-life of 6c (t1/2β = 240.93 min) is ten times longer than 2-ME and the area under the curve was seven times (AUC0-tmin = 2068.20 ± 315.74 μg mL?1 min) higher than 2-ME, respectively. Whereas 5e had similar pharmacokinetic behavior with 2-ME (t1/2β = 22.28 min) with a t1/2β of 29.5 min. 6c had higher blood concentration, longer actuation duration and better suppression rate against S180 mouse ascites tumor than 2-methoxyestradiol.
Synthesis and structure-activity relationships of 16-modified analogs of 2-methoxyestradiol
Agoston, Gregory E.,Shah, Jamshed H.,LaVallee, Theresa M.,Zhan, Xiaoguo,Pribluda, Victor S.,Treston, Anthony M.
, p. 7524 - 7537 (2008/03/28)
A series of 16-modified 2-methoxyestradiol analogs were synthesized and evaluated for antiproliferative activity toward HUVEC and MDA-MB-231 cells, and for susceptibility to conjugation. In addition, the estrogenicity of these analogs was accessed by meas
Effects of altering the electronics of 2-methoxyestradiol on cell proliferation, on cytotoxicity in human cancer cell cultures, and on tubulin polymerization
Edsall, Allison B.,Mohanakrishnan, Arasambattu K.,Yang, Donglai,Fanwick, Philip E.,Hamel, Ernest,Hanson, Arthur D.,Agoston, Gregory E.,Cushman, Mark
, p. 5126 - 5139 (2007/10/03)
A series of new analogues of 2-methoxyestradiol (1) were synthesized to further elucidate the relationships between structure and activity. The compounds were designed to diminish the potential for metabolic deactivation at positions 2 and 17 and were analyzed as inhibitors of tubulin polymerization and for cytotoxicity. 17α-Methyl-β-estradiol (30), 2-propynyl-17α- methylestradiol (39), 2-ethoxy-17-(1′-methylene)estra-1,3,5(10)-triene-3- ol (50) and 2-ethoxy-17α-methylestradiol (51) showed similar or greater tubulin polymerization inhibition than 2-methoxyestradiol (1) and contained moieties that are expected to inhibit deactivating metabolic processes. All of the compounds tested were cytotoxic in the panel of 55 human cancer cell cultures, and generally, the derivatives that displayed the most activity against tubulin were also the most cytotoxic.
