171734-73-9

Basic information

• Product Name: 1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde
• Synonyms: 1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde
• CAS NO: 171734-73-9
• Molecular Formula: C₁₆H₁₂BrNO
• Molecular Weight: 314
• Mol File: 171734-73-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde(171734-73-9)
• EPA Substance Registry System: 1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde(171734-73-9)

Safety Data

• Hazardous Substances Data: 171734-73-9(Hazardous Substances Data)

Usage

Description

1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde is a chemical compound with the molecular formula C15H11BrNO. It is a derivative of indole, a heterocyclic aromatic organic compound. 1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde features a bromine atom and an aldehyde group attached to the indole ring, along with a benzyl group. Its unique structure and properties make it a versatile building block in organic synthesis and medicinal chemistry research, particularly for the development of indole-based compounds with potential pharmaceutical applications.

Uses

Used in Pharmaceutical Research:
1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde is used as a building block for the synthesis of various indole-based compounds. Its application in pharmaceutical research is due to its potential to be incorporated into new drugs with specific therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde serves as a key intermediate for creating a range of complex organic molecules. Its utility stems from the presence of the bromine atom, which can be used for further functionalization, and the aldehyde group, which is a versatile handle for chemical reactions.
Used in Medicinal Chemistry:
1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde is used as a starting material in medicinal chemistry to develop new drugs. The indole core is a common structural motif in many bioactive molecules, and the presence of the bromine and benzyl groups in this compound allows for the fine-tuning of its biological activity and pharmacokinetic properties.
Used in Chemical Research:
1-(2-bromobenzyl)-1H-indole-3-carboxaldehyde is also utilized in chemical research to study the reactivity of different functional groups and to explore novel reaction pathways. Its unique structure makes it an interesting subject for academic research and the development of new synthetic methods.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 171734-91-1 1-<2-(2-bromophenyl)-2-oxoethyl>-1H-indole-3-carboxaldehyde 
• 171734-95-5 1-<2-(2-bromophenyl)-1-oxoethyl>-1H-indole-3-carboxaldehyde 
• 120-72-9 indole 

Downstream Products

• 210426-41-8 1-(2-bromobenzyl)-3-hydroxymethyl-1H-indole 
• 1207733-64-9 C₂₀H₁₇BrN₄O 
• 1207615-65-3 (Z)-5-((1-(2-bromobenzyl)-1H-indol-3-yl)methylene)-imidazolidine-2,4-dione 
• 1207615-76-6 C₂₀H₁₄BrN₃O₃ 
• 1536462-83-5 C₂₂H₁₈BrN₃O₃ 
• 1593928-70-1 (E)-3-(1-(2-bromobenzyl)-1H-indol-3-yl)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)prop-2-en-1-one 

Relevant articles and documents

Synthesis, characterization, and biological evaluation of indole aldehydes containing N-benzyl moiety

The present study describes the synthesis, characterization and biological evaluation of N-benzyl indole aldehydes. The biological activities of the newly synthesized compounds were examined by investigating their antioxidant and anti-inflammatory activities. The potential of these compounds as an antioxidant was determined by 2,2-diphenylpicrylhydrazyl, Nitric oxide, Superoxide, peroxide radical scavenging methods. We found that aldehydes 4a, 4b, 4c, and 4e and shows promising in vitro DPPH scavenging antioxidant activity while aldehyde 4b and 4e show good in vitro anti-inflammatory activity.

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.

Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines

The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. The analogs 3a, 3b, 3d-3g, 3k and 3l were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC50 values a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization.