474706-38-2

Basic information

• Product Name: 4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE
• Synonyms: 4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE;4-Bromo-5-(4-methoxyphenyl)pyrazole;4-bromo-3-(4-methoxyphenyl)-1H-Pyrazole
• CAS NO: 474706-38-2
• Molecular Formula: C₁₀H₉BrN₂O
• Molecular Weight: 253.1
• Mol File: 474706-38-2.mol

Chemical Properties

• Boiling Point: 399.0±32.0 °C(Predicted)
• Appearance: /
• Density: 1.520±0.06 g/cm3(Predicted)
• PKA: 12.31±0.50(Predicted)
• CAS DataBase Reference: 4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE(474706-38-2)
• EPA Substance Registry System: 4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE(474706-38-2)

Safety Data

• Hazardous Substances Data: 474706-38-2(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE is used as a building block for the synthesis of biologically active compounds, contributing to the development of new pharmaceutical agents.
Used in Drug Discovery:
In the field of drug discovery, 4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE is utilized for its potential biological activities, which may be harnessed in the research and development of novel therapeutic agents.
Used in Pharmaceutical Industry:
4-BROMO-3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE is employed in the pharmaceutical industry for its potential to target specific biological pathways or molecular targets, aiding in the creation of innovative drugs for various medical conditions.

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 18096-70-3 3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one 
• 27069-17-6 3-p-methoxyphenylpyrazole 

Downstream Products

• 474706-44-0 4-bromo-3-(4-methoxyphenyl)-1-trityl-1H-pyrazole 

Relevant articles and documents

Design, synthesis and biological evaluation of novel vicinal diaryl-substituted 1H-Pyrazole analogues of combretastatin A-4 as highly potent tubulin polymerization inhibitors

A series of 3-(3′,4′,5′-trimethoxyphenyl)-4-substituted 1H-pyrazole and their related 3-aryl-4-(3′,4′,5′-trimethoxyphenyl)-1-H-pyrazole regioisomeric derivatives, prepared as cis-rigidified combretastatin A-4 (CA-4) analogues, were synthesized and evaluated for their in vitro antiproliferative against six different cancer cell lines and, for selected highly active compounds, inhibitory effects on tubulin polymerization, cell cycle effects and in vivo potency. We retained the 3′,4′,5′-trimethoxyphenyl moiety as ring A throughout the present investigation, and a structure-activity relationship (SAR) information was obtained by adding electron-withdrawing (OCF3, CF3) or electron-releasing (alkyl and alkoxy) groups on the second aryl ring, corresponding to the B-ring of CA-4, either at the 3- or 4-position of the pyrazole nucleus. In addition, the B-ring was replaced with a benzo[b]thien-2-yl moiety. For many of the compounds, their activity was greater than, or comparable with, that of CA-4. Maximal activity was observed with the two regioisomeric derivatives characterized by the presence of a 4-ethoxyphenyl and a 3′,4′,5′-trimethoxyphenyl group at the C-3 and C-4 positions, and vice versa, of the 1H-pyrazole ring. The data showed that the 3′,4′,5′-trimethoxyphenyl moiety can be moved from the 3- to the 4-position of the 1H-pyrazole ring without significantly affecting antiproliferative activity. The most active derivatives bound to the colchicine site of tubulin and inhibited tubulin polymerization at submicromolar concentrations. In vivo experiments, on an orthotopic murine mammary tumor, revealed that 4c inhibited tumor growth even at low concentrations (5 mg/kg) compared to CA-4P (30 mg/kg).