15903-94-3 Usage
Description
6-Benzyloxyindole is an indole derivative characterized as a colorless crystalline solid. It is a significant compound in the field of organic chemistry, known for its diverse applications in various industries due to its unique chemical properties.
Uses
Used in Pharmaceutical Industry:
6-Benzyloxyindole is used as an antiviral and antitumor agent for its potential therapeutic effects against viral infections and cancerous cells. Its ability to modulate cellular processes and inhibit the growth of pathogens makes it a valuable compound in the development of new drugs.
Used in Enantioselective Synthesis:
6-Benzyloxyindole serves as a reactant for the enantioselective synthesis of quaternary carbon-containing 3-(3-indolyl)isoindolin-1-ones. This application is crucial in the production of chiral molecules, which are essential in the pharmaceutical industry for their specific biological activities.
Used in Friedel-Crafts Alkylation:
As a reactant in Friedel-Crafts alkylation reactions with hydroxyisoindolinones, 6-Benzyloxyindole contributes to the formation of new carbon-carbon bonds, leading to the synthesis of various organic compounds with potential applications in different industries.
Used in Synthesis of β-Heteroarylated Ketones:
6-Benzyloxyindole is employed as a reactant for the direct and regioselective synthesis of β-heteroarylated ketones. These compounds are valuable in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Preparation of HCV Inhibitors:
6-Benzyloxyindole is utilized as a reactant for the preparation of hepatitis C virus (HCV) inhibitors. Its role in the development of antiviral drugs targeting HCV highlights its importance in the fight against this viral infection.
Used in Preparation of PKC Inhibitors:
The compound is also used as a reactant for the preparation of protein kinase C (PKC) inhibitors. PKC inhibitors have potential applications in the treatment of various diseases, including cancer, making 6-Benzyloxyindole a valuable component in the development of these therapeutic agents.
Used in Preparation of CB2 Cannabinoid Receptor Ligands:
6-Benzyloxyindole is used as a reactant for the preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands. These ligands have potential applications in the treatment of various conditions, including inflammation, pain, and neurodegenerative diseases.
Check Digit Verification of cas no
The CAS Registry Mumber 15903-94-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,9,0 and 3 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 15903-94:
(7*1)+(6*5)+(5*9)+(4*0)+(3*3)+(2*9)+(1*4)=113
113 % 10 = 3
So 15903-94-3 is a valid CAS Registry Number.
InChI:InChI=1/C15H13NO/c1-2-4-12(5-3-1)11-17-14-7-6-13-8-9-16-15(13)10-14/h1-10,16H,11H2
15903-94-3Relevant articles and documents
Total Synthesis of Bruceolline i
Scarpi, Dina,Faggi, Cristina,Occhiato, Ernesto G.
, p. 2384 - 2388 (2017)
The first total synthesis of the natural product bruceolline I, isolated in small quantities from the ethanol extract of Brucea mollis stems, was achieved in 29% yield over nine steps and with high enantiomeric purity (>98%). The key step of the process i
Indolyl Azaspiroketal Mannich Bases Are Potent Antimycobacterial Agents with Selective Membrane Permeabilizing Effects and in Vivo Activity
Nyantakyi, Samuel Agyei,Li, Ming,Gopal, Pooja,Zimmerman, Matthew,Dartois, Véronique,Gengenbacher, Martin,Dick, Thomas,Go, Mei-Lin
supporting information, p. 5733 - 5750 (2018/06/20)
The inclusion of an azaspiroketal Mannich base in the membrane targeting antitubercular 6-methoxy-1-n-octyl-1H-indole scaffold resulted in analogs with improved selectivity and submicromolar activity against Mycobacterium tuberculosis H37Rv. The potency enhancing properties of the spiro-fused ring motif was affirmed by SAR and validated in a mouse model of tuberculosis. As expected for membrane inserting agents, the indolyl azaspiroketal Mannich bases perturbed phospholipid vesicles, permeabilized bacterial cells, and induced the mycobacterial cell envelope stress reporter promoter piniBAC. Surprisingly, their membrane disruptive effects did not appear to be associated with bacterial membrane depolarization. This profile was not uniquely associated with azaspiroketal Mannich bases but was characteristic of indolyl Mannich bases as a class. Whereas resistant mycobacteria could not be isolated for a less potent indolyl Mannich base, the more potent azaspiroketal analog displayed low spontaneous resistance mutation frequency of 10-8/CFU. This may indicate involvement of an additional envelope-related target in its mechanism of action.
Structure-based de novo design, synthesis, and biological evaluation of the indole-based PPARγ ligands (I)
Dong, Xiaochun,Zhang, Zhenshan,Wen, Ren,Shen, Jianhua,Shen, Xu,Jiang, Hualiang
, p. 5913 - 5916 (2007/10/03)
MCSS and LeapFrog, two de novo drug design programs, were used for the novel indole-based PPARγ ligands' study. The designed compounds were synthesized and tested for the PPARγ protein binding activities in vitro. Out of the compounds that were synthesize
