50823-86-4

Usage

InChI:InChI=1/C12H12N2O2/c15-14(16)8-5-6-12-10(7-8)9-3-1-2-4-11(9)13-12/h5-7,13H,1-4H2

Upstream product

• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 1919-96-6 cyclohexanone p-nitrophenylhydrazone 
• 108-94-1 cyclohexanone 
• 100-16-3 4-nitrophenylhydrazone 
• 7664-93-9 sulfuric acid 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 110-52-1 1,4-dibromo-butane 
• 6146-52-7 5-nitroindole 
• 100-63-0 phenylhydrazine 

Downstream Products

• 65796-52-3 3-amino-5,6,7,8-tetrahydro-9H-carbazole 
• 3077-85-8 3-Nitro-carbazol 
• 39581-69-6 9-methyl-6-nitro-2,3,4,9-tetrahydro-1H-carbazole 

Relevant academic research and scientific papers

Synthesis and evaluation of 2,3,4,9-tetrahydro-1H-carbazole derivatives as selective acetylcholinesterase inhibitors: Potential anti-Alzheimer's agents

Alzheimer's disease is an irreversible, progressive brain disorder that slowly destroys memory and cognition skills. Dysfunction of acetylcholine containing neurons in the brain contributes substantially to the cognitive decline observed in Alzheimer's disease. Hence, our focus is to synthesize cholinesterase inhibitors. A series (22 compounds) of 6- and 9-substituted derivatives of 2,3,4,9-tetrahydro-1H-carbazole have been prepared and in vitro evaluated for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition by Ellman's method. By comparing selectivity with standard drug donepezil, amino derivative 3, methylamino derivative 4 and butyl nitro derivative 17 have been found to be selective AChE inhibitors. Borsche-Drechsel cyclization reaction has been carried out to synthesize 2,3,4,9-tetrahydrocarbazole ring followed by nitration, reduction and derivative synthesis.

Process for synthesizing [b]-cycloindole derivatives

The invention discloses a method for synthesizing [b]-cyclized indole derivatives. The method comprises the steps as follows: alkylation ring-closing domino reactions at C2 and C3 sites of indole aresequentially realized with a one-pot process under the action of alkali and a palladium catalyst with norbornene as a transient guide medium and dihaloalkane as an alkylation reagent, and the [b]-cyclized indole derivatives are effectively synthesized. The method has mild conditions, commercially available indole is directly used as a substrate, a pre-functionalization process is omitted, reactionsteps are reduced, the atom economy is higher, simple indole micromolecular structures are modified, and the [b]-cyclized indole derivatives can be further applied to medicine or total synthesis research and the like and have higher potential value and broad application prospects in medicinal chemistry and other fields.

SBA-15-Pr-SO3H catalyzed one-pot synthesis of indole derivatives via Fischer indole pathway

In this work, an efficient, user-friendly, and simple procedure was reported for the preparation of indole derivatives catalyzed by the heterogeneous SBA-15-Pr-SO3H via Fischer indole pathway. The title compounds were synthesized from various arylhydrazines and ketones in the presence of 3 mol% of the catalyst in the refluxing ethanol.

Annulation of Indoles with 1,n-Dibromoalkanes by a Pd(II)-Catalyzed and Norbornene-Mediated Reaction Cascade

Employing 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane as biselectrophiles, the annulation of indoles was probed in the presence of PdCl 2 (MeCN) 2 as a catalyst and norbornene as a transpositional ligand. Ring formation to a five-membered ring was observed at positions C2 and N, while annulation of a six-membered ring occurred at positions C2 and C3. The latter cascade process was successfully applied to the direct synthesis of 1,2,3,4-tetrahydrocarbazoles from indoles (11 examples, 31-68% yield). Seven-membered-ring annulation was feasible by an initial coupling at positon C2 followed by alkylation at C3.

Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids

An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.

Method for preparing indole compounds through catalysis of ionic liquid

The invention relates to a green synthesis method of one type of indole derivatives. The method is characterized by taking sulfonic acid ionic liquid as a catalyst, taking aliphatic ketone, aromatic ketone and aromatic hydrazine hydrochloride as raw materials, reacting in water, filtering and drying a reaction mixture to obtain indole compounds. The method is simple to operate; the raw materials are low intoxicity and low in costs; the reaction condition is mild; the product is easy to separate; the synthesis process is environmentally-friendly; the indole compounds are high in purity; the catalyst can be directly reused without treatment; the method is green and environmentally-friendly, and is suitable for industrial production.

Discovery of ITX 4520: A highly potent orally bioavailable hepatitis C virus entry inhibitor

The manuscript reports an identification of a highly potent, orally bioavailable hepatitis C virus entry inhibitor through optimization of a previously reported class of molecules (1) that were not stable in the rat plasma. Compound 39 (ITX 4520) exhibited an excellent PK profile in both rats and dogs with good oral exposure, half-life and oral bioavailability. The compound is also well-tolerated in the preliminary in vivo toxicity studies and has been selected as a pre-clinical candidate for our HCV clinical pipeline.

Novel SO3H-functionalized ionic liquids catalyzed a simple, green and efficient procedure for Fischer indole synthesis in water under microwave irradiation

Novel SO3H-functionalized ionic liquids were successfully applied as catalysts for one-pot Fischer indole synthesis under microwave irradiation and in a water medium. Various types of indoles were prepared using single-carbonyl ketones/aldehydes or cyclohexandiones with aryhydrazine hydrochlorides in 86-96% yields in water under microwave irradiation. The indole products could be conveniently separated from the reaction mixture through filtration, and the catalytic system of [(HSO3-p)2im] [CF3SO3]/H2O could be reused directly without any treatment. The entire process is simple, time saving, and environmentally friendly.

Fischer indole synthesis catalyzed by novel SO3H-functionalized ionic liquids in water

Novel SO3H-functionalized ionic liquids bearing two alkyl sulfonic acid groups in the imidazolium cations were designed and successfully applied as catalysts for the one-pot Fischer indole synthesis in water medium. The sequence of the catalytic activity observed in the transformation was in good agreement with the Bronsted acidity order determined by the Hammett method. Various types of indoles from single-carbonyl ketones/aldehydes and cyclohexandiones were provided in 68-96% yields using the catalytic system of [(HSO3-p)2im][HSO4]/H2O. The indole products could be conveniently separated from the reaction mixture by filtration and the dissolved catalyst could be regenerated by treatment with a strongly acidic cation exchange resin, which meant the whole process was performed in water without using any organic solvents.

DERIVATIVES OF SUBSTITUTED FUSED RING CYCLOINDOLES AND METHODS OF THEIR USE

Disclosed herein are derivatives of substituted fused ring cycloindole useful, inter alia, in combating Hepatitis C infection and entry into cells.