401-25-2Relevant articles and documents
Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones
Li, Zhiping,Luo, Yani,Lv, Leiyang,Nishihara, Yasushi,Tian, Tian
supporting information, p. 9276 - 9279 (2021/09/20)
A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.
Anxiolytic-like effects of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis
Da Settimo, Federico,Simorini, Francesca,Taliani, Sabrina,La Motta, Concettina,Marini, Anna Maria,Salerno, Silvia,Bellandi, Marusca,Novellino, Ettore,Greco, Giovanni,Cosimelli, Barbara,Da Pozzo, Eleonora,Costa, Barbara,Simola, Nicola,Morelli, Micaela,Martini, Claudia
supporting information; experimental part, p. 5798 - 5806 (2009/08/07)
Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R1-R5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal f
3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT2A receptor antagonists
Rowley,Hallett,Goodacre,Moyes,Crawforth,Sparey,Patel,Marwood,Patel,Thomas,Hitzel,O'Connor,Szeto,Castro,Hutson,Macleod
, p. 1603 - 1614 (2007/10/03)
The development of very high affinity, selective, and bioavailable h5-HT2A receptor antagonists is described. By investigation of the optimal position for the basic nitrogen in a series of 2-phenyl-3-piperidylindoles, it was found that with the basic nitrogen at the 3-position of the piperidine it was not necessary to further substitute the piperidine in order to obtain good binding at h5-HT2A receptors. This meant the compounds no longer had high affinity at the IKr potassium channel, an issue with previous series of 2-aryl-3-(4-piperidyl)indoles. Improvements could be made to oral bioavailability in this series by reduction of the pKa of the basic nitrogen, by adding a fluorine atom to the piperidine ring, leading to 3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (17). Metabolic studies with this compound identified oxidation at the 6-position of the indole as a major route in vitro and in vivo in rats. Blocking this position with a fluorine atom led to 6-fluoro-3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (22), an antagonist with 0.06 nM affinity for h5-HT2A receptors, with bioavailability of 80% and half-life of 12 h in rats.
