142769-36-6

Basic information

• Product Name: 1H-Indol-5-ol, 1-(phenylmethyl)-
• CAS NO: 142769-36-6
• Molecular Formula: C15H13NO
• Molecular Weight: 223.274
• Mol File: 142769-36-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1H-Indol-5-ol, 1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indol-5-ol, 1-(phenylmethyl)-(142769-36-6)
• EPA Substance Registry System: 1H-Indol-5-ol, 1-(phenylmethyl)-(142769-36-6)

Safety Data

• Hazardous Substances Data: 142769-36-6(Hazardous Substances Data)

Usage

Derivative of

Indole

Pharmacological properties

Neuroprotective agent, inhibitory effects on monoamine oxidase

Potential use

Synthesis of novel pharmaceutical compounds

Role in organic chemistry

Reagent for various synthetic transformations

Upstream product

• 16382-24-4 1-benzyl-5-(benzyloxy)-1H-indole 
• 92433-38-0 1-benzyl-5-chloro-1H-indole 
• 1421358-73-7 C₁₈H₁₅NO 
• 100-44-7 benzyl chloride 
• 1006-94-6 5-methoxylindole 
• 100-39-0 benzyl bromide 
• 1215-59-4 5-benzyloxy-1H-indole 
• 16382-21-1 1-benzyl-5-methoxyindole 

Downstream Products

• 710982-51-7 1-benzyl-5-(2-chloro-4-trifluoromethyl-phenoxy)-1H-indole 
• 1616268-51-9 4-([1,4'-bipiperidin]-1'-ylmethyl)-1-benzyl-1H-indol-5-ol 
• 172733-35-6 4-[[3-(2-amino-1,2-dioxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester 
• 1026492-71-6 4-(1-Benzyl-3-chlorooxalyl-1H-indol-5-yloxy)-butyric acid ethyl ester 
• 161459-96-7 YM-32906 
• 161460-39-5 4-[(1-benzyl-1H-indol-5-yl)oxy]-3-chlorobenzonitrile 
• 1000786-91-3 C₂₇H₂₃ClN₂OS 

Relevant articles and documents

Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions

The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).

2-Aryl-3,3,3-trifluoro-2-hydroxypropionic acids: A new class of protein tyrosine phosphatase 1B inhibitors

A new series of non-peptidic, mono-acid protein tyrosine phosphatase 1B (PTP1B) inhibitors has been identified by structure-based design. Compounds with 2-(indol-3-yl)- and 2-phenyl-3,3,3-trifluoro-2-hydroxypropionic acid core units targeted at the enzyme's primary site and a hydrophobic chlorophenylthiazole extension in its 2° site exhibit 3-60 μM IC50s for PTP1B inhibition in an Sf9 cell-based assay.

A novel class of inhibitors for human steroid 5α-reductase: Synthesis and biological evaluation of indole derivatives. II

In a search for novel nonsteroidal inhibitors of human prostatic 5α- reductase, we found a new series of indole derivatives that showed potent inhibitory activities for the human enzyme. Among them, 4-[(1-benzyl-1- Hindol-5-yl)oxy]-3-chlorobenzoic acid (2d, YM-32906) showed more potent inhibitory activity than finasteride with an IC50 value of 0.44 nM. 3- Chloro-4-{[1-(4-phenoxybenzyl)-1H-indol-5-yl]oxy}benzoic acid (2m) showed inhibitory activities for both human and rat prostatic 5α-reductase with IC50 values of 2.1 and 73 nM, respectively. The synthesis and structure- activity relationships of these indole derivatives are presented.