58697-34-0

Basic information

• Product Name: 2-(3,5-dimethoxyphenyl)-1H-indole
• Synonyms: 2-(3,5-dimethoxyphenyl)-1H-indole
• CAS NO: 58697-34-0
• Molecular Weight: 253.301
• Mol File: 58697-34-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-(3,5-dimethoxyphenyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,5-dimethoxyphenyl)-1H-indole(58697-34-0)
• EPA Substance Registry System: 2-(3,5-dimethoxyphenyl)-1H-indole(58697-34-0)

Safety Data

• Hazardous Substances Data: 58697-34-0(Hazardous Substances Data)

Upstream product

• 1314806-80-8 C₁₆H₁₃BrO₂ 
• 615-43-0 2-iodophenylamine 
• 171290-52-1 1-Ethynyl-3,5-dimethoxy-benzene 
• 1338091-83-0 (E)-N′-(3,5-dimethoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 95-52-3 2-Fluorotoluene 
• 19179-31-8 3,5-dimethoxy-benzonitrile 
• 96406-93-8 3,5-dimethoxyphenylhydrazine 

Relevant articles and documents

Cascade annulative π-extension for the rapid construction of carbazole based polyaromatic hydrocarbons

A Br?nsted acid catalyzed cascade benzannulation strategy for the one-pot synthesis of densely populated poly-aryl benzo[a]carbazole architectures is disclosed from easily affordable fundamental commodities. The efficacy of this technique was further validated via the concise synthesis of structurally unique carbazole based poly-aromatic hydrocarbons. Furthermore, the photo-physical properties of the synthesized compounds are thoroughly investigated.

One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles

A one-pot Barluenga coupling between N-tosylhydrazones and nitro-benzyl bromide, followed by deoxygenation of ortho-nitrostyrenes, and subsequent cyclization has been developed, providing a new way to synthesize various C2-arylindoles. This method exhibits a good substrate scope and functional group tolerance, and it allows an access to NH-free indoles, which can present a potential utility in medicinal chemistry applications.

Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1

In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.