62367-64-0Relevant articles and documents
Photochromic Indolyl Fulgimides as Chromo-pharmacophores Targeting Sirtuins
Simeth, Nadja A.,Altmann, Lisa-Marie,W?ssner, Nathalie,Bauer, Elisabeth,Jung, Manfred,K?nig, Burkhard
, p. 7919 - 7927 (2018/06/11)
Sirtuins are involved in epigenetic regulation, the pathogenesis of cancer, and several metabolic and neurodegenerative diseases. Despite being a promising drug target, only one small molecule passed class II clinical trials to date. Deriving a better mechanistic understanding is hence crucial to find new modulators. We previously reported on a series of dithienyl maleimides as photochromic tool compounds. However, their photochromic behavior was limited. To improve the interconversion and stability of both photoisomers, we replaced the dithienyl maleimide with a fulgimide as a photochromic core to result in biologically active compounds reversibly addressable with purple and orange light. We characterize the obtained compounds regarding their spectroscopic properties, their photostability, and binding characteristics toward sirtuins resulting in a fully remote-controllable Sirtuin modulator using visible light as the external stimulant.
Palladium-catalyzed regioselective C-H fluoroalkylation of indoles at the C4-position
Borah, Arun Jyoti,Shi, Zhuangzhi
supporting information, p. 3945 - 3948 (2017/04/11)
An exclusive catalytic C4-selective fluoroalkylation of indoles with highly active (1H, 1H-perfluoroalkyl)mesityliodonium triflate has been described. The key to its high regioselectivity is the appropriate choice of an easily accessible, cheap and removable directing group at the C3 position in the presence of a Pd(OAc)2 catalyst. Besides indole fluoroalkylation, the application of this strategy in other heteroarenes such as benzo[b]thiophene is also described.
Ruthenium-catalyzed annulation of alkynes with amides via formyl translocation
Wu, Cui-Yan,Hu, Ming,Liu, Yu,Song, Ren-Jie,Lei, Yong,Tang, Bo-Xiao,Li, Rong-Jiang,Li, Jin-Heng
supporting information; experimental part, p. 3197 - 3199 (2012/05/07)
The first example of Ru-catalyzed intramolecular annulation of alkynes with amides via formyl translocation has been developed, which provides an efficient approach for the synthesis of 1H-indole-3-carbaldehydes. The Royal Society of Chemistry 2012.
Intramolecular C-N bond addition of amides to alkynes using platinum catalyst
Shimada, Tomohiro,Nakamura, Itaru,Yamamoto, Yoshinori
, p. 10546 - 10547 (2007/10/03)
The intramolecular aminoacylation of alkynes using ortho-alkynylacetanilides proceeds in very high yields in the presence of PtCl2 catalyst. This reaction provides not only a useful procedure for synthesizing 2,3-disubstituted indoles at once from ortho-alkynylaniline derivatives, but also an interesting mechanistic aspect; the intramolecular C-N bond addition of amides to alkynes takes place readily in the presence of Pt(II) catalyst. Copyright
Electrophilic ipso-Substitutions. Part 1. Reaction of 3-Substituted Indoles with Nitronium and Nitrosonium Ions
Colonna, Martino,Greci, Lucedio,Poloni, Marino
, p. 628 - 632 (2007/10/02)
3-Substituted indoles react with nitronium and nitrosonium ions to yield 3-nitroindole.In both cases the reaction was interpreted as an electrophilic ipso-substitution.The reaction mechanism is interpreted by hypothesizing the formation of a ?-complex-like intermediate, wich is some cases is preceded by an electron-transfer process.An order for the leaving abilities of the different electrofugal groups is discussed.
