126522-16-5Relevant articles and documents
Discovery of 5-(pyridin-3-yl)-1H-indole-4,7-diones as indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors
Kong, Kai-min,Liu, Bing-zhi,Meng, Guang-rong,Zhang, Jia-wei,Zhang, Qian
, (2020/01/03)
Early studies demonstrated that over expression of indoleamine 2,3-dioxygenase (IDO1) in tumor microenvironment results in tumor immune escape. Herein, in order to simplify the structure of two kinds of IDO1 inhibitors from marine alkaloid, Exiguamine A and Tsitsikammamines, we designed, synthesized a series of 1H-indole-4,7-dione derivatives and evaluated their inhibitory activity in IDO1 enzyme and in IFN-γ stimulated Hela cells in vitro. The structure-activity relationship demonstrated that 5-(pyridin-3-yl)-1H-indole-4,7-dione is a promising scaffold for IDO1 inhibitors and most compounds with this core showed moderate inhibition potency at micromole level. Our further enzyme kinetics experiments reveal that these new developed compounds might act as reversible competitive inhibitors of IDO1.
Efficient synthesis of novel six-member ring-fused quinoline derivatives via the Friedlaender reaction
Yang, Dingqiao,Guo, Wei,Cai, Yuepeng,Jiang, Lasheng,Jiang, Kailing,Wu, Xiaobing
, p. 229 - 233 (2008/09/19)
Novel quinolines fused with a six-member ring 5a-j were prepared in high yields (75-95%) via the Friedlaender reaction of dimethoxy-substituted o-aminobenzaldehydes of 3a or 3b with cyclic ketones 4, respectively. The structures of 5aj were determined by IR, 1H NMR, MS, and elemental analysis.
Incorporation of Quinoline-5,8-quinone Moiety into Polyaza Cavities
Thummel, Randolph P.,Chirayil, Sara,Hery, Christophe,Lim, Jean-Luc,Wang, Tie-Lin
, p. 1666 - 1671 (2007/10/02)
Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde.Friedlaender condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones.The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlaender approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.