17518-01-3

Basic information

• Product Name: 1-Propanone, 1-[3,4-bis(phenylmethoxy)phenyl]-2-bromo-
• CAS NO: 17518-01-3
• Molecular Formula: C23H21BrO3
• Molecular Weight: 425.31500
• Mol File: 17518-01-3.mol

Chemical Properties

• CAS DataBase Reference: 1-Propanone, 1-[3,4-bis(phenylmethoxy)phenyl]-2-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 1-[3,4-bis(phenylmethoxy)phenyl]-2-bromo-(17518-01-3)
• EPA Substance Registry System: 1-Propanone, 1-[3,4-bis(phenylmethoxy)phenyl]-2-bromo-(17518-01-3)

Safety Data

• Hazardous Substances Data: 17518-01-3(Hazardous Substances Data)

Upstream product

• 17269-65-7 1-(3,4-bis(benzyloxy)phenyl)propan-1-one 
• 100-39-0 benzyl bromide 
• 7451-98-1 3',4'-dihydroxypropiophenone 

Downstream Products

• 76467-33-9 N-[2-(3,4-Bis-benzyloxy-phenyl)-1-methyl-2-oxo-ethyl]-N-phenethyl-formamide 
• 1610763-23-9 1-(3,4-bis(benzyloxy)phenyl)-2-((4-(methoxymethoxy)phenyl)amino)propan-1-one 
• 1610763-25-1 2-(3,4-bis(benzyloxy)phenyl)-3-methyl-1H-indol-5-ol 
• 1610763-27-3 3-((2-(3,4-bis(benzyloxy)phenyl)-3-methyl-1H-indol-5-yl)oxy)-propan-1-ol 
• 1610763-29-5 2-((2-(3,4-bis(benzyloxy)phenyl)-3-methyl-1H-indol-5-yl)oxy)ethyl acetate 
• 1610763-31-9 2-((2-(3,4-bis(benzyloxy)phenyl)-3-methyl-1H-indol-5-yl)oxy)ethanol 
• 1610763-32-0 4-(5-hydroxy-3-methyl-1H-indol-2-yl)benzene-1,2-diol 
• 1610763-34-2 4-(5-(2-hydroxyethoxy)-3-methyl-1H-indol-2-yl)benzene-1,2-diol 
• 1610763-36-4 4-(5-(3-hydroxypropoxy)-3-methyl-1H-indol-2-yl)benzene-1,2-diol 
• 1610763-41-1 5-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methyl-1H-indole 
• 1610763-42-2 5-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-1,3-dimethyl-1H-indole 
• 1610763-43-3 5-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methyl-1-propyl-1H-indole 
• 1610763-44-4 1-benzyl-5-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methyl-1H-indole 
• 1610763-45-5 4-(5-hydroxy-1,3-dimethyl-1H-indol-2-yl)benzene-1,2-diol 

Relevant articles and documents

Synthesis, Antiproliferative Effect, and Topoisomerase II Inhibitory Activity of 3-Methyl-2-phenyl-1 H-indoles

A series of 3-methyl-2-phenyl-1H-indoles was prepared and investigated for antiproliferative activity on three human tumor cell lines, HeLa, A2780, and MSTO-211H, and some structure-activity relationships were drawn up. The GI50 values of the most potent compounds (32 and 33) were lower than 5 μM in all tested cell lines. For the most biologically relevant derivatives, the effect on human DNA topoisomerase II relaxation activity was investigated, which highlighted the good correlation between the antiproliferative effect and topoisomerase II inhibition. The most potent derivative, 32, was shown to induce the apoptosis pathway. The obtained results highlight 3-methyl-2-phenyl-1H-indole as a promising scaffold for further optimization of compounds with potent antiproliferative and antitopoisomerase II activities.

Bazedoxifene-scaffold-based mimetics of solomonsterols A and B as novel pregnane x receptor antagonists

Pregnane X receptor (PXR), a member of the NR1I nuclear receptor family, acts as a xenobiotic sensor and a paramount transcriptional regulator of drug-metabolizing enzymes and transporters. The overexpression of PXR in various cancer cells indicates the importance of PXR as a drug target for countering multidrug resistance in anticancer treatments. We describe the discovery of novel bazedoxifene-scaffold-based PXR antagonists inspired by the marine sulfated steroids solomonsterol A and B as natural leads. A luciferase reporter assay on a PXR-transfected HepG2 cell line identified compounds 19-24 as promising PXR antagonists. Further structure-activity relationship studies of the most active PXR antagonist from the series (compound 20, IC50 = 11 μM) revealed the importance of hydroxyl groups as hydrogen-bond donors for PXR antagonistic activity. PXR antagonists 20 and 24 (IC50 = 14 μM), in addition to the downregulation of PXR expression, exhibited inhibition of PXR-induced CYP3A4 expression, which illustrates their potential to suppress PXR-regulated phase-I drug metabolism.