- Discovery of 5-(pyridin-3-yl)-1H-indole-4,7-diones as indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors
-
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.
- Kong, Kai-min,Liu, Bing-zhi,Meng, Guang-rong,Zhang, Jia-wei,Zhang, Qian
-
supporting information
(2020/01/03)
-
- A simple route to polysubstituted indoles exploiting azide induced furan ring opening
-
A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.
- Abaev, Vladimir T.,Plieva, Anastasiya T.,Chalikidi, Petrakis N.,Uchuskin, Maxim G.,Trushkov, Igor V.,Butin, Alexander V.
-
supporting information
p. 4150 - 4153
(2014/09/30)
-
- Efficient synthesis of novel six-member ring-fused quinoline derivatives via the Friedlaender reaction
-
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.
- Yang, Dingqiao,Guo, Wei,Cai, Yuepeng,Jiang, Lasheng,Jiang, Kailing,Wu, Xiaobing
-
p. 229 - 233
(2008/09/19)
-
- A FRIEDLAENDER APPROACH TO 3-SUBSTITUTED 2,5,8-(1H)-QUINOLINETRIONES
-
An efficient method is proposed for the preparation of 3-substituted carbostyrilquinone derivatives, based on Friedlaender synthesis of the 5,8-dialkoxyquinolines followed by cerium ammonium nitrate oxidative demethylation.
- Blanco, Ma del Mar,Avendano, Carmen,Cabezas, Nieves,Menendez, J. Carlos
-
p. 1387 - 1398
(2007/10/02)
-
- Incorporation of Quinoline-5,8-quinone Moiety into Polyaza Cavities
-
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.
- Thummel, Randolph P.,Chirayil, Sara,Hery, Christophe,Lim, Jean-Luc,Wang, Tie-Lin
-
p. 1666 - 1671
(2007/10/02)
-
- STUDIES ON THE SYNTHESIS OF FUSED HETEROCYCLES FROM o-AMINOCARBONYL COMPOUNDS
-
Convenient preparations of 6-amino-2,5-dimethoxyacetophenone and benzaldehyde (3,6), and heterocyclization of these to produce benzisoxazol, quinoline amd cinnolinesystems are described.
- Fernandez, M.,Lopez, F.,Tapia, R.,Valderrama, J. A.
-
p. 3087 - 3096
(2007/10/02)
-