17790-93-1

Usage

InChI:InChI=1/C11H13N/c1-8(2)11-7-9-5-3-4-6-10(9)12-11/h3-8,12H,1-2H3

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 615-43-0 2-iodophenylamine 
• 67-56-1 methanol 
• 134792-65-7 2-(1-Methoxy-1H-indol-2-yl)-propan-2-ol 
• 81784-65-8 4-Methyl-3-oxo-pentanoic acid hydroxy-phenyl-amide 
• 82185-43-1 N-(trimethylsilyl)-o-toluidine 
• 97-62-1 Ethyl isobutyrate 
• 174275-12-8 2-(3-methyl-1-butynyl)aniline 
• 70361-43-2 2-methyl-1-(2-nitrophenyl)butan-2-one 
• 65826-92-8 1-(2-aminophenyl)-3-methyl-2-butanol 
• 26686-10-2 4,7-dihydro-1H-indole 
• 67-64-1 acetone 
• 120-72-9 indole 
• 75-26-3 isopropyl bromide 

Downstream Products

• 329015-27-2 2,5-dichloro-3-(2-isopropyl-1H-indol-3-yl)[1,4]benzoquinone 
• 1143570-96-0 (+)-(S)-2-isopropylindoline 

Relevant academic research and scientific papers

Deconstruction of the α4β2 nicotinic acetylcholine receptor positive allosteric modulator desformylflustrabromine

Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of α4β2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for α4β2 versus α7 nACh receptors. Pharmacophoric features for the allosteric modulation of α4β2 nACh receptors by 1 were identified.

Method for synthesizing 2-substituted indole derivative under catalysis of copper

The invention relates to a method for synthesizing a 2-substituted indole derivative under the catalysis of copper, which comprises the following step of: reacting by taking copper acetylacetonate (Cu (acac) 2) as a catalyst and taking indole and halogenated hydrocarbon as raw materials to obtain the 2-substituted indole derivative. Compared with the prior art, the method has the advantages that the copper acetylacetonate Cu (acac) 2 which is low in price, easy to obtain and stable in property is used as the catalyst, the method is green and economical, the catalyst is used for catalyzing the indole and halogenated hydrocarbon to react to synthesize the 2-substituted indole derivative, the reaction condition is mild, and the selectivity and yield of the product are high; and the synthesis method is simple and green, the 2-substituted indole derivative is directly constructed by using cheap and easily available raw materials indole and halogenated hydrocarbon, and the 2-substituted indole derivative has good substrate universality and has wide application value in the fields of pharmaceutical chemistry, fine chemical industry and the like.

AMINOPYRIMIDINE COMPOUNDS, PREPARATION METHODS AND USES THEREOF

Provided herein are novel compounds, for example, compounds having a Formula (I) or Formula (II), or a pharmaceutically acceptable salt thereof. Also provided herein are methods of preparing the compounds and methods of using the compounds, for example, for treating various cancer described herein, such as lung cancer (e.g., non-small cell lung cancer).

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Lithiation of 1-alkoxyindole derivatives

Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.

CHEMICAL SUBSTANCES WHICH INHIBIT THE ENZYMATIC ACTIVITY OF HUMAN KALLIKREIN-RELATED PEPTIDASE 6 (KLK6)

The invention relates to compounds which are suitable for the treatment of a disease associated with kallikrein-like peptidase 6 overexpression and to pharmaceutical compositions containing such compounds. The invention further relates to a kit of parts comprising such compounds or pharmaceutical compositions.

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.

A facile one-pot method to synthesise 2-alkylated indole and 2,2′-bis(indolyl)methane derivatives using ketones as electrophiles and their anion sensing ability

Indole derivatives are of great importance because of their biological activity and application in technology. This study explores the synthesis of 2-alkylated indoles derivatives and 2,2′-bis(indolyl)methanes, and their application in anion sensing. The synthesis of a wide range of 2-alkylated indoles and some 2,2′-bis(indolyl)methanes, which cannot be synthesized by previously reported methods, was for the first time accomplished employing dipole exchange of the indole ring towards electrophilic substitution. Some of the indole derivatives exhibited selective recognition and sensing ability towards F- and HSO4- anions through naked-eye detectable color changes. The sensing details of the indole derivatives were also evaluated using UV-Vis spectroscopy and 1H NMR titration techniques.

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.

Efficient synthesis of 2-mono and 2,3-disubstituted indoles via palladium-catalyzed oxidation of aminoalcohols

Efficient synthesis of 2-mono- and 2,3-disubstituted indoles has been accomplished via palladium-catalyzed oxidation of aminoalcohols.