885521-25-5

Basic information

• Product Name: 4-AMINO-3-BROMO (1H)INDAZOLE
• Synonyms: 4-AMINO-3-BROMO (1H)INDAZOLE;1H-INDAZOL-4-AMINE,3-BROMO-;3-BroMo-1H-indazol-4-aMine;3-Bromo-1H-indazol-4-ylamine
• CAS NO: 885521-25-5
• Molecular Formula: C7H6BrN3
• Molecular Weight: 212.05
• Mol File: 885521-25-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 431.3±25.0 °C(Predicted)
• Appearance: /
• Density: 1.867±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13.43±0.40(Predicted)
• CAS DataBase Reference: 4-AMINO-3-BROMO (1H)INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-3-BROMO (1H)INDAZOLE(885521-25-5)
• EPA Substance Registry System: 4-AMINO-3-BROMO (1H)INDAZOLE(885521-25-5)

Safety Data

• Hazardous Substances Data: 885521-25-5(Hazardous Substances Data)

Usage

General Description

4-Amino-3-Bromo (1H)Indazole is a chemical compound categorized under indazoles, which are nitrogenous aromatic organic compounds featuring a bicyclic structure made of two fused rings, namely benzene and pyrazole. This particular chemical is commonly used in various scientific and pharmaceutical research and development activities due to its reactive nature that allows it to serve as a building block in the synthesis of more complex compounds. Its bromine atom enables halogen bonding which is often leveraged in drug design. As with many chemical compounds, it needs to be handled with care, adhering to safety measures due to potential risks and hazards associated with inappropriate handling.

Upstream product

• 74209-17-9 3-bromo-4-nitro-1H-indazole 
• 64-17-5 ethanol 

Relevant articles and documents

Synthesis, antiproliferative and apoptotic activities of N-(6(4)-indazolyl)-benzenesulfonamide derivatives as potential anticancer agents

Recently, it has been reported that compounds bearing a sulfonamide moiety possess many types of biological activities, including anticancer activity. The present work reports the synthesis and antiproliferative evaluation of some N-(6(4)-indazolyl)benzenesulfonamides and 7-ethoxy-N-(6(4)-indazolyl) benzenesulfonamides. All compounds were evaluated for their in vitro antiproliferative activity against three tumor cell lines: A2780 (human ovarian carcinoma) A549 (human lung adenocarcinoma) and P388 (murine leukemia). The results indicated that sulfonamides 2c, 3c, 6d, 8, 13, 3b and 16 were endowed with a pharmacologically interesting antiproliferative activity with compounds 2c and 3c showing the lower IC50 (from 0.50 ± 0.09 to 1.83 ± 0.52 μM and from 0.58 ± 0.17 to 5.83 ± 1.83 μM, respectively). Moreover, these indazoles were able to trigger apoptosis through the upregulation of the typical apoptosis markers p53 and bax. As regard to the hypothetic targets of these compounds, a preliminary docking analysis showed that all compounds seemed to interact with β-tubulin, in particular compound 3b that showed the lower Ki. The cytofluorimetric analysis of the cell cycle phases indicates that all compounds, when administered at their IC 75, caused a block in the G2/M phase of the cell cycle with the generation of subpopulations of cells with a number of chromosome >4n. When the IC50s were applied we observed a prevalent block in the G0/G1 phase except for compounds 16 and 8 where a partial G2/M block was present with a concomitant decrease of cells in the G0/G1 and S phases of the cell cycle. Altogether these results suggest a possible, but not exclusive, interaction with microtubules.