117954-38-8Relevant articles and documents
Cascade Reaction to Selectively Synthesize Multifunctional Indole Derivatives by IrIII-Catalyzed C?H Activation
Chai, Xin-Yue,Xu, Hui-Bei,Dong, Lin
supporting information, p. 13123 - 13127 (2021/08/13)
An effective and condition-controlled way to synthesize with high selectivity a variety of functionalized indoles with potent biological properties has been developed. Notably, 2,4-dialkynyl indole products were obtained by direct double C?H bond alkynylation, whereas alkynyl at the C4 position could convert to carbonyl to generate 2-alkynyl-3,4-diacetyl indoles fast and effectively. Additionally, a one-pot relay catalytic reaction led to 2,5-di-alkynyl-3,4-diacetyl indoles when using a carbonyl group as the directing group and by controlling the type and quantity of additives. A possible mechanism was proposed based on many studies including deuterium-exchange experiments, the necessary conditions of product conversion, and the effect of water on the reaction.
Indol-3-ylcycloalkyl ketones: Effects of N1 substituted indole side chain variations on CB2 cannabinoid receptor activity
Frost, Jennifer M.,Dart, Michael J.,Tietje, Karin R.,Garrison, Tiffany R.,Grayson, George K.,Daza, Anthony V.,El-Kouhen, Odile F.,Yao, Betty B.,Hsieh, Gin C.,Pai, Madhavi,Zhu, Chang Z.,Chandran, Prasant,Meyer, Michael D.
, p. 295 - 315 (2010/06/11)
Several 3-acylindoles with high affinity for the CB2 cannabinoid receptor and selectivity over the CB1 receptor have been prepared. A variety of 3-acyl substituents were investigated, and the tetramethylcyclopropyl group was found to lead to high affinity CB2 agonists (5, 16). Substitution at the N1-indole position was then examined. A series of aminoalkylindoles was prepared and several substituted aminoethyl derivatives were active (23-27, 5) at the CB2 receptor.Astudy of N1 nonaromatic side chain variants provided potent agonists at the CB2 receptor (16, 35-41, 44-47, 49-54, and 57-58). Several polar side chains (alcohols, oxazolidinone) were well-tolerated for CB2 receptor activity (41, 50), while others (amide, acid) led to weaker or inactive compounds (55 and 56). N1 aromatic side chains also afforded several high affinity CB2 receptor agonists (61, 63, 65, and 69) but were generally less potent in an in vitro CB2 functional assay than were nonaromatic side chain analogues.
3-CYCLOALKYLCARBONYL INDOLES AS CANNABINOID RECEPTOR LIGANDS
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Page/Page column 72, (2008/06/13)
The present invention provides novel compounds of Formula (I), which are CB2 selective ligands useful for the treatment of pain.
The synthesis of a Series of (α-Amino)indol-3-yl Ketones
Sanchez, Joseph P.,Parcell, Robert F.
, p. 469 - 474 (2007/10/02)
A series of -2-methyl-1-propanones and cyclopentylmethanones has been synthesized by a variety of reductive reactions performed on the corresponding series of (α-azido)indol-3-yl ketones.One of the more interesting reductive procedures involved the palladium-catalyzed decomposition of formic acid with the formation of hydrogen in situ.The (α-azido)ketones were prepared in excellent yield by the displacement of the tertiary bromine atom from the (α-bromo)ketones using sodium azide in N,N-dimethylformamide.Bromination was accomplished by using either cupric bromide in ethyl acetate/chloroform or phenyltrimethylammonium tribromide in tetrahydrofuran.
