17591-06-9Relevant academic research and scientific papers
Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents
Zhang, Jun,Torabi Kohlbouni, Saeedeh,Borhan, Babak
supporting information, p. 14 - 17 (2019/01/08)
The selective oxidation of C2-alkyl-substituted indoles to 3-oxindole and the selective C-H oxygenation or amination of C2,C3-dialkyl-substituted indoles at C2 are reported under mild conditions. The position of the alkyl substitution on the indole directs the reaction to different pathways under similar conditions.
Visible-light-induced metal and reagent-free oxidative coupling of: Sp 2 C-H bonds with organo-dichalcogenides: Synthesis of 3-organochalcogenyl indoles
Rathore, Vandana,Kumar, Sangit
, p. 2670 - 2676 (2019/06/03)
Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C-H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone at room temperature. This benign protocol allows one to access a wide range of 3-arylselenylindoles, 3-arylthioindoles and even 3-aryltelluroindoles with good to excellent yields. Various functionalities namely, methoxy, and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C-H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene radical cation and a superoxide radical anion. Subsequently, reaction of the radical cation with aryl dichalcogenides provides a diaryl chalcogenyl cation which upon removal of protons gave unsymmetrical 3-indolyl aryl chalcogenides.
Ring-Opening Diarylation of Siloxydifluorocyclopropanes by Ag(I) Catalysis: Stereoselective Construction of 2-Fluoroallylic Scaffold
Song, Xiaoning,Xu, Cong,Du, Dongxu,Zhao, Ziming,Zhu, Dongsheng,Wang, Mang
supporting information, p. 6542 - 6545 (2017/12/26)
A silver-catalyzed, defluorination ring-opening diarylation of siloxy 2,2-difluorocyclopropanes, with two arenes, to directly prepare polysubstituted 2-fluoroallylic compounds, is described. This multicomponent reaction proceeds smoothly in good stereoselectivity, which is due to a chelation-controlled addition of arenes to α-fluorinated ketone intermediate.
3-(3,4,5-Trimethoxyphenylselenyl)-1 H -indoles and their selenoxides as combretastatin A-4 analogs: Microwave-assisted synthesis and biological evaluation
Wen, Zhiyong,Xu, Jingwen,Wang, Zhiwei,Qi, Huan,Xu, Qile,Bai, Zhaoshi,Zhang, Qian,Bao, Kai,Wu, Yingling,Zhang, Weige
, p. 184 - 194 (2015/01/08)
A series of 3-(3,4,5-trimethoxyphenylselenyl)-1H-indoles and their selenoxides were designed as a new class of combretastatin A-4 (CA-4) analogs. The B ring and the cis double bond of CA-4 were replaced by an indole moiety and selenium atom, respectively. A facile and efficient microwave-assisted synthesis of 3-arylselenylindoles was developed to prepare the target compounds, which were then evaluated for antiproliferative activity against three human cancer cell lines using an MTT assay. Most of these compounds exhibited significant antiproliferative activity, with some showing nanomolar IC50 values. Tubulin polymerization and immunostaining experiments revealed that 13a potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a similar manner to CA-4. Docking studies demonstrated that 13a adopts an orientation similar to that of CA-4 at the colchicine binding site on tubulin.
Synthesis of indoles through Rh(III)-catalyzed C-H cross-coupling with allyl carbonates
Gong, Tian-Jun,Cheng, Wan-Min,Su, Wei,Xiao, Bin,Fu, Yao
, p. 1859 - 1862 (2014/03/21)
A practical Rh-catalyzed reaction was developed to achieve 2-alkyl-substituted indole synthesis. The reaction can tolerate a variety of synthetically important functional groups. The indole products can also be transformed into other important skeletons. Two bioactive compounds, that is indomethacin and pravadoline were prepared using the new method.
Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides
Alford, Joshua S.,Davies, Huw M. L.
supporting information, p. 10266 - 10269 (2014/08/05)
An effective method for aminoacylation of indoles and pyrroles has been achieved. The transformation involves a multicomponent one-pot cascade reaction between indoles or pyrroles, ynol ethers, and sulfonyl azides, creating four different bonds regioselectively through N-sulfonyltriazole intermediates. The oxo-tryptamines and oxo-pyrroloethanamines are generated in moderate to high yields under mild reaction conditions.
In situ generation of PhI+CF3 and transition-metal-free oxidative sp2 C-H trifluoromethylation
Xu, Cong,Liu, Jingxin,Ming, Wenbo,Liu, Yingjie,Liu, Jun,Wang, Mang,Liu, Qun
supporting information, p. 9104 - 9109 (2013/07/26)
These things are sent to tri us: The introduction of CF3 units into organic molecules is important and requires the development of convenient trifluoromethylating reagents. Here, PhI+CF3, an acyclic electrophilic "CF3
Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides
Nadres, Enrico T.,Lazareva, Anna,Daugulis, Olafs
supporting information; experimental part, p. 471 - 483 (2011/04/15)
The palladium-catalyzed direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and electron-poor aryl chlorides as well as chloropyridine coupling partners can be used, and arylated heterocycles are obtained in moderate to good yields. Optimization of base, ligand, and solvent is required for achieving best results.
SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN
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Page/Page column 66-67, (2011/05/05)
Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and pro-drugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain)
1H NMR studies on the reductively triggered release of heterocyclic and steroid drugs from 4,7-dioxoindole-3-methyl prodrugs
Ferrer, Sandra,Naughton, Declan P.,Threadgill, Michael D.
, p. 3445 - 3454 (2007/10/03)
Hypoxia is a feature of several disease states, including cancer and rheumatoid arthritis. Prodrug systems which, after bioreduction, selectively release active drugs in these tissues may be important in therapy. An improved preparation of 1,2-dimethyl-3-hydroxymethyl-5-methoxyindole-4,7-dione was developed. Mitsunobu coupling with (5-substituted) isoquinolin-1-ones (potent inhibitors of poly(ADP-ribose)polymerase) gave 1-(1,2-dimethyl-4,7-dioxo-5-methoxyindol-3-ylmethoxy)isoquinolines and N-(1,2-dimethyl-4,7-dioxo-5-methoxyindol-3-ylmethyl)isoquinolin-1-ones. Similar coupling with the anticancer drug pentamethylmelamine gave its potential prodrug 1,2-dimethyl-3-(N-(4,6-bis(dimethylamino)-1,3,5-triazin-2-yl)-N- methylaminomethyl)-5-methoxyindole-4,7-dione. Treatment of sodium prednisolone hemisuccinate with 3-chloromethyl-1,2-dimethyl-5-methoxyindole-4,7-dione gave an analogous candidate prodrug of the anti-inflammatory drug prednisolone. In a chemical model system for bioreduction, SnCl2 in CDCl3/CD3OD triggered rapid stoichiometric release of isoquinolin-1-ones from the O-linked prodrugs but not from the N-linked analogues. Use of this system allowed the release process to be monitored in situ by 1H NMR spectroscopy. Diethyl hydrazine-1,2-dicarboxylate was found to reduce SnIV to SnII, making the overall reductive release catalytic in tin. The reduced (hydroquinone) prodrug may have a short lifetime under these reductive conditions, meaning that only good leaving groups are expelled. Thus 1-(1,2-dimethyl-4,7-dioxo-5-methoxyindol-3-ylmethoxy)isoquinolines and analogues may be useful as reductively triggered prodrugs.
