20289-26-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxyindole is used as a substrate-binding molecule for cytochrome P 450 2A6, an enzyme involved in the metabolism of various drugs and other xenobiotics. The N297Q and I300V mutants of this enzyme have an expanded substrate specificity, allowing for the oxidation of substituted indoles, which can be useful in drug metabolism studies and the development of new pharmaceuticals.
Used in Organic Chemistry:
4-Benzyloxyindole is used in the synthesis of 4-alkyloxy-aminoalkyl indole derivatives, which are valuable compounds in organic chemistry with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science. The synthesis of these derivatives can lead to the discovery of new compounds with unique properties and potential uses.

Reactions

4-Benzyloxyindole was used in the synthesis of 4-alkyloxy-aminoalkyl indole derivatives. Reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition Reactant for preparation of indoles by Bartoli reductive cyclization as useful intermediates in medicinal chemistry research Reactant for synthesis of carbon-11-labeled 4-aryl-4H-chromenes as new PET agents for imaging of apoptosis in cancer Reactant for preparation of HCV inhibitors. Reactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands Reactant for preparation of 4-aryl-4H-chromenes as apoptosis inducers

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 34, 1990The Journal of Organic Chemistry, 51, p. 4294, 1986 DOI: 10.1021/jo00372a037Tetrahedron Letters, 24, p. 4561, 1983 DOI: 10.1016/S0040-4039(00)85955-9

InChI:InChI=1/C15H13NO/c1-2-5-12(6-3-1)11-17-15-8-4-7-14-13(15)9-10-16-14/h1-10,16H,11H2

Upstream product

• 2380-94-1 1H-indol-4-ol 
• 100-39-0 benzyl bromide 
• 108-24-7 acetic anhydride 
• 78283-30-4 2-benzyloxy-6-nitrophenyl acetaldehyde 
• 109532-27-6 2-Amino-6-(benzyloxy)-α-chloracetophenon 
• 20876-37-3 2-benzyloxy-6-nitrotoluene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 5762-56-1 tris(dimethylamino)methane 
• 4426-72-6 hydrazine carboxamide 
• 22630-08-6 tris(piperidino)-methane 
• 39731-09-4 4-benzyloxylindole-2-carboxylic acid 
• 4837-88-1 6-methoxy-2-nitrotoluene 
• 83-42-1 6-chloro-2-nitrotoluene 
• 100-44-7 benzyl chloride 

Downstream Products

• 2873-49-6 1-<4-(benzyloxy)indol-3-yl>-2-nitropropane 
• 83788-93-6 E-3-(2-nitrovinyl)-4-benzyloxyindole 
• 87824-18-8 3-(4-benzyloxy-indol-3-yl)-2-nitro-5-oxa-hexanoic acid ethyl ester 
• 30000-78-3 1-benzyl-4-(benzyloxy)-1H-indole 
• 91164-53-3 5-(Benzyloxy)-β-carbolin-3-carbonsaeure-ethylester 
• 7042-71-9 4-benzyloxyindole-3-carbaldehyde 
• 129625-20-3 3,3',3''-Tris(4-benzyloxyindolyl)methane 
• 118052-07-6 2-(4-(benzyloxy)-1H-indol-3-yl)-N-methyl-2-oxoacetamide 
• 173844-32-1 (4-Benzyloxy-1H-indol-3-yl)-phenyl-acetic acid ethyl ester 
• 133437-68-0 4-benzyloxy-1-[2-(4-morpholinyl)ethyl]-1H-indole 
• 250672-67-4 (R,S)-(+/-)-3-(4-benzyloxyindol-3-yl)-N-methylsuccinimide 
• 270588-32-4 4-benzyloxy-1-(triisopropylsilyl)indole 
• 480435-72-1 3-(4-benzyloxy-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
• 840538-48-9 4-benzyloxy-3-iodo-1H-indole 

Relevant academic research and scientific papers

Synthetic method of 4-hydroxyindole

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of 4-hydroxyindole. Aiming at the problems existing in industrial production of 4-hydroxyindole in the prior art, the technical scheme of the invention is as follows: the method comprises the following steps: (1) protecting hydroxyl in a compound 3 by using a protective group to obtaina compound 4; (2) reacting the compound 4 with N, N-dimethylformamide dimethyl acetal to obtain a compound 5; (3) mixing the compound 5 with NH2NH2.H2O and MeOH, and carrying out a reaction to obtaina compound 6; and (4) removing the protective group of the compound 6 to obtain 4-hydroxyindole. According to the method for synthesizing 4-hydroxyindole, the cost of starting materials is low, the reaction conditions in the synthesis process are mild, operation is convenient, aftertreatment is simple, and the yield is high.

INDOLE DERIVATIVES AS ALPHA-1 -ANTITRYPSIN MODULATORS FOR TREATING ALPHA-1 -ANTITRYPSIN DEFICIENCY (AATD)

Indole derivatives as alpha-l-antitrypsin modulators for treating alpha-l-antitrypsin deficiency (AATD).

A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides

A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

mTORC1 MODULATORS

Provided herein, inter alia, are methods and compounds for inhibiting mTORC1 and for treating diseases associated with mTORC1 activity.

COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING CFTR

The present disclosure is directed to disclosed compounds that modulate, e.g., address underlying defects in cellular processing of CFTR activity.

LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF

Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

FLUORINATED LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF

Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

Total synthesis of thiaplakortone A: Derivatives as metabolically stable leads for the treatment of malaria

Thiaplakortone A (3a), an antimalarial natural product, was prepared by an operationally simple and scalable synthesis. In our efforts to deliver a lead compound with improved potency, metabolic stability, and selectivity, the synthesis was diverted to access a series of analogues. Compounds 3a-d showed nanomolar activity against the chloroquine-sensitive (3D7) Plasmodium falciparum line and were more active against the chloroquine- and mefloquine-resistant (Dd2) P. falciparum line. All compounds are "Rule-of-5" compliant, and we show that metabolic stability can be enhanced via modification at either the primary or pyrrole nitrogen. These promising results lay the foundation for the development of this structurally unprecedented natural product.

INDOLE, INDOLINE DERIVATIVES, COMPOSITIONS COMPRISING THEM AND USES THEREOF

The invention provides indole and indoline derivatives and slats thereof, compositions comprising them and uses thereof for the treatment of diseases and disorders.

Highly chemoselective reduction using a Rh/C-Fe(OAc)2 system: Practical synthesis of functionalized indoles

Here, we report a highly effective and chemoselective method of preparing substituted indoles from (E)-2-nitropyrrolidinostyrenes via hydrogenation in the presence of a rhodium catalyst doped by additives such as Ni(NO 3)2·6H2O, Fe(OAc)2 or Co(acac)3. These hydrogenation conditions may also be applied to other substrates. Aromatic nitro compounds and olefins can be selectively reduced in the presence of aromatic benzyl ethers, aromatic halides and aromatic aldehydes.