3610-42-2Relevant articles and documents
Synthesis of Vinca Alkaloids and Related Compounds, XXXIV: Synthesis of (3S,14S,16S)-Bromovincamines and Bromoapovincamines by Regioselective Bromination
Szabo, Lajos,Dobay, Laszlo,Kalaus, Gyoergy,Gacs-Baitz, Eszter,Tamas, Jozsef,Szantay, Csaba
, p. 781 - 789 (1987)
By bromimation of the iminium salt 2a (X=Cl), the 9-bromo derivative 2c (X=ClO4) is obtained in isomer-free state.Bromination of the lactam 8d leads to ca. 7.5:1 mixture of 11-bromo (8c) and 9-bromo (8a) lactams.These precursors have been used to synthesize 9-, 10- and 11-bromovincamines (11a-c), and 9-, 10- and 11-bromoapovincamines (12a-c).
Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow
Ranjan, Prabhat,Ojeda, Gerardo M.,Sharma, Upendra K.,Van der Eycken, Erik V.
, p. 2442 - 2446 (2019/01/29)
A metal-free, phosphine-catalyzed intramolecular “umpolung Michael addition” on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope of five- and six-membered spiroindol(en)ines in moderate to excellent yields in batch as well as under continuous-flow conditions. Triphenylphosphine-catalyzed nucleophilic activation of alkynes allows the exclusive formation of exo-product under mild reaction conditions.
Design, synthesis and biological evaluation of tryptamine salicylic acid derivatives as potential antitumor agents
Xiong, Runde,He, Dongxiu,Deng, Xiangping,Liu, Juan,Lei, Xiaoyong,Xie, Zhizhong,Cao, Xuan,Chen, Yanming,Peng, Junmei,Tang, Guotao
, p. 573 - 583 (2019/04/30)
A series of tryptamine salicylic acid derivatives were synthesized and their antiproliferative activity against MGC-803, MCF-7, HepG2, A549 and HeLa cell lines was evaluated. The structure-activity relationship (SAR) study revealed that different substitutions of the C5 and C3′-C5′ positions have certain effects on the anti-proliferation activity. The growth assay revealed that N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide (E20) showed the most potent and broad-spectrum anticancer inhibition of all the cell lines evaluated, and was only more potent than 5-Fu for the gastric cancer cell line. Preliminary studies indicated that compound E20 could inhibit colony formation and migration of MGC-803 cells. The flow cytometry (FCM) results showed that compound E20 arrested the cell cycle in the G2/M phase and induced apoptosis of MGC-803 cells in a concentration-dependent manner. In addition, the western blot results showed that E20 can down-regulate the expression of hexokinase 2. Our studies suggest that the framework of N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide may be consider as a new type of chemical for designing effective anti-cancer drugs targeting gastric cancer cells.