90734-97-7Relevant articles and documents
Effect of 4-Methoxyindole-3-Carbinol on the proliferation of colon cancer cells in vitro, when treated alone or in combination with indole-3-Carbinol
Kronbak, Remy,Duus, Fritz,Vang, Ole
, p. 8453 - 8459 (2010)
Consumption of cruciferous vegetables and cancer prevention seem to be positively associated. We present an easy two-step synthesis for 4-methoxyindole-3-carbinol (4MeOI3C), the expected breakdown product of 4-methoxyglucobrassicin during ingestion. 4MeOI3C inhibited the proliferation of human colon cancer cells DLD-1 and HCT 116 with IC50 values of 116 μM and 96 μM, respectively, after 48 h in vitro, and is therefore a more potent inhibitor than indole-3-carbinol (I3C). 4MeOI3C and I3C combined in different molar ratios inhibited proliferation in a nearly additive to slightly synergistic manner. Proliferation was inhibited by 100 μM 4MeOI3C after 48 h without affecting cell cycle phase distribution, indicating an overall-slowdown effect on the cell cycle. However, 200 μM 4MeOI3C caused a very high level of cell death and an accumulation of living cells in the G0/G 1 phase, indicating a concentration-dependent mode of action. We conclude that 4MeOI3C might play a role in the cancer preventive effect of cruciferous vegetables.
First Electrophilic Substitution of 4-Methoxyindole with Triethyl Orthoformate as an a1-Synthon
Pindur, Ulf,Witzel, Helmut
, p. 77 - 80 (1990)
4-Methoxyindole (2) reacts with triethyl orthoformate (1a) under proton catalysis to yield the functionalized indoles 3a - 3e in dependence on the reaction conditions.The attack of the electrophile takes place regiospecifically at the 3-position of the indole 2.
Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles
Xie, Tao,Sui, Qi-Bang,Qin, Lu-Zhe,Wen, Xiaoan,Sun, Hongbin,Xu, Qing-Long,Zhen, Le
supporting information, p. 5518 - 5529 (2021/05/04)
A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.
Discovery and synthesis of novel indole derivatives-containing 3-methylenedihydrofuran-2(3H)-one as irreversible LSD1 inhibitors
Liu, Hong-Min,Suo, Feng-Zhi,Li, Xiao-Bo,You, Ying-Hua,Lv, Chun-Tao,Zheng, Chen-Xing,Zhang, Guo-Chen,Liu, Yue-Jiao,Kang, Wen-Ting,Zheng, Yi-Chao,Xu, Hai-Wei
, p. 357 - 372 (2019/05/17)
Lysine-specific demethylase 1 (LSD1), demethylase against mono- and di - methylated histone3 lysine 4, has emerged as a promising target in oncology. More specifically, it has been demonstrated as a key promoter in acute myeloid leukemia (AML), and several LSD1 inhibitors have already entered into clinical trials for the treatment of AML. In this paper, a series of new indole derivatives were designed and synthesized based on a lead compound obtained by a high-throughput screening with our in-house compound library. Among the synthetic compounds, 9e was characterized as a potent LSD1 inhibitor with an IC50 of 1.230 μM and can inhibit the proliferation of THP-1 cells effectively. And most importantly, this is the first irreversible LSD1 inhibitor that is not derived from monoamine oxidase inhibitors. Hence, the discovery of 9e may serve as a proof of concept work for AML treatment.
