20289-26-3 Usage
Description
4-Benzyloxyindole is an off-white crystalline solid with a few darker (brown) particles. It is an indole derivative that serves as a substrate-binding molecule for cytochrome P 450 2A6, with N297Q and I300V mutants displaying an expansion of substrate specificity for oxidizing substituted indoles.
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
Check Digit Verification of cas no
The CAS Registry Mumber 20289-26-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,2,8 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 20289-26:
(7*2)+(6*0)+(5*2)+(4*8)+(3*9)+(2*2)+(1*6)=93
93 % 10 = 3
So 20289-26-3 is a valid CAS Registry Number.
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
20289-26-3Relevant articles and documents
Synthetic method of 4-hydroxyindole
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, (2021/03/30)
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.
A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides
Sun, Wanwan,Chen, Xiaobei,Hu, Ying,Geng, Huihui,Jiang, Yuanrui,Zhou, Yuxin,Zhu, Wenjing,Hu, Min,Hu, Haohua,Wang, Xingyi,Wang, Xinli,Zhang, Shilei,Hu, Yanwei
supporting information, (2020/10/05)
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.
COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING CFTR
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Paragraph 0205, (2017/08/01)
The present disclosure is directed to disclosed compounds that modulate, e.g., address underlying defects in cellular processing of CFTR activity.