174367-69-2

Basic information

• Product Name: 1-(3-BROMOBENZYL)-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: IVK/1270475;1-(3-BROMOBENZYL)-1H-INDOLE-3-CARBALDEHYDE;1-(3-bromobenzyl)indole-3-carbaldehyde;1-[(3-bromophenyl)methyl]-3-indolecarboxaldehyde;1-[(3-bromophenyl)methyl]indole-3-carbaldehyde
• CAS NO: 174367-69-2
• Molecular Formula: C₁₆H₁₂BrNO
• Molecular Weight: 314.19
• Mol File: 174367-69-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(3-BROMOBENZYL)-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-BROMOBENZYL)-1H-INDOLE-3-CARBALDEHYDE(174367-69-2)
• EPA Substance Registry System: 1-(3-BROMOBENZYL)-1H-INDOLE-3-CARBALDEHYDE(174367-69-2)

Safety Data

• Hazardous Substances Data: 174367-69-2(Hazardous Substances Data)

Usage

Structure

A derivative of indole with a bromine atom and a benzyl group attached to the 3-position of the indole ring.

Organic synthesis

Used as a building block for various pharmaceutical compounds.

Medicinal chemistry

Serves as a starting material for the development of new drugs.

Antibacterial and antifungal activities

Exhibits potential as a therapeutic agent against bacterial and fungal infections.

Biochemical and cellular studies

Used as a fluorescent probe to interact with biomolecules and study their properties.

Interaction with biomolecules

Capable of binding to specific target molecules, making it useful for detecting and analyzing biological processes.

Potential drug development

Its unique structure and properties make it a valuable tool for the development of new pharmaceutical compounds with various therapeutic applications.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 823-78-9 meta-bromobenzyl bromide 

Downstream Products

• 1593928-72-3 (E)-3-(1-(3-bromobenzyl)-1H-indol-3-yl)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)prop-2-en-1-one 
• 261637-59-6 bis[1-[(3-bromophenyl)methyl]-1H-indole-3-]methane 
• 210426-42-9 1-[(3-bromophenyl)methyl]-1H-indole-3-methanol 

Relevant articles and documents

Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents

A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the most potent cytotoxic activity against all tested cancer cell lines including multidrug resistant phenotype, which inhibits cancer cell growth with IC50 values ranging from 0.22 to 1.80 μM. Furthermore, 49b significantly induced cell cycle arrest in G2/M phase and inhibited the polymerization of tubulin. Molecular docking analysis demonstrated the interaction of 49b at the colchicine binding site of tubulin. In experiments in vivo, 49b exerted potent anticancer activity in HepG2 human liver carcinoma in BALB/c nude mice. These results indicated these compounds are promising inhibitors of tubulin polymerization for the potential treatment of cancer.

3-(Azolylmethyl)-1H-indoles as selective P450 aromatase inhibitors

The synthesis of 1-(halobenzyl) and 1-tosyl-3-(1H-imidazol-1-ylmethyl)-1H-indoles, 1-(halobenzyl) and 1-tosyl-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-indoles and 1-(halobenzyl)-3-(4H-1,2,4-triazol-4-ylmethyl)-1H-indoles is described. 3-(Azolylmethyl)-1H-indoles were obtained in three steps from 1H-indole-3-carbaldehyde (1) by benzylation or tosylation, reduction and azole moiety fixation. In an alternative method, the bromo intermediates issued from the corresponding alcohols were condensed with the azolium sodium salts. Inhibitory activity against P450(arom) and P450(17α), and influence on retinoic acid metabolism were evaluated. Three imidazole compounds exhibited potent and selective aromatase inhibitory activity.