1217-83-0

Basic information

• Product Name: 2-(4-CHLOROPHENYL)-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 2-(4-CHLOROPHENYL)-1H-INDOLE-3-CARBALDEHYDE;2-(4-CHLOROPHENYL)-1H-INDOLE-3-CARBOXALDEHYDE;2-(4-CHLOROPHENYL)INDOLE-3-CARBOXALDEHYDE
• CAS NO: 1217-83-0
• Molecular Formula: C₁₅H₁₀ClNO
• Molecular Weight: 255.7
• Mol File: 1217-83-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 485.6 °C at 760 mmHg
• Flash Point: 247.5 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 1.4E-09mmHg at 25°C
• Refractive Index: 1.712
• CAS DataBase Reference: 2-(4-CHLOROPHENYL)-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLOROPHENYL)-1H-INDOLE-3-CARBALDEHYDE(1217-83-0)
• EPA Substance Registry System: 2-(4-CHLOROPHENYL)-1H-INDOLE-3-CARBALDEHYDE(1217-83-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 1217-83-0(Hazardous Substances Data)

Usage

General Description

2-(4-Chlorophenyl)-1H-indole-3-carbaldehyde is a chemical compound with the formula C15H10ClNO. It is an aromatic aldehyde with a substituted indole ring, containing a chlorine atom on the phenyl group. 2-(4-CHLOROPHENYL)-1H-INDOLE-3-CARBALDEHYDE is commonly used in organic synthesis and medicinal chemistry as a building block for the preparation of various heterocyclic compounds and pharmaceuticals. It exhibits potential biological activities and pharmacological properties, making it a valuable intermediate in the synthesis of diverse bioactive molecules. Additionally, 2-(4-Chlorophenyl)-1H-indole-3-carbaldehyde may have applications in the development of drugs for various therapeutic purposes.

InChI:InChI=1/C15H10ClNO/c16-11-7-5-10(6-8-11)15-13(9-18)12-3-1-2-4-14(12)17-15/h1-9,17H

Upstream product

• 1211-35-4 2-(4-chlorophenyl)-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 62-53-3 aniline 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 99-91-2 para-chloroacetophenone 
• 57845-08-6 p-chloroacetophenone phenylhydrazone 
• 100-63-0 phenylhydrazine 

Downstream Products

• 126479-67-2 4-{[1-[2-(4-Chloro-phenyl)-1H-indol-3-yl]-meth-(Z)-ylidene]-amino}-N,N-diphenyl-benzamide 
• 96821-68-0 (4-Phenyl-piperazin-1-yl)-acetic acid [1-[2-(4-chloro-phenyl)-1H-indol-3-yl]-meth-(E)-ylidene]-hydrazide 
• 96821-72-6 (4-o-Tolyl-piperazin-1-yl)-acetic acid [1-[2-(4-chloro-phenyl)-1H-indol-3-yl]-meth-(E)-ylidene]-hydrazide 
• 1392103-84-2 2-(4-chlorophenyl)-3-(4,5-dihydro-3-phenylisoxazol-5-yl)-1H-indole 
• 1392103-85-3 2-(4-chlorophenyl)-3-(3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)-1H-indole 
• 1392103-86-4 3-[3-(4-bromophenyl)-4,5-dihydroisoxazol-5-yl]-2-(4-chlorophenyl)-1H-indole 
• 1392103-87-5 2-(4-chlorophenyl)-3-(4,5-dihydro-3-p-tolylisoxazol-5-yl)-1H-indole 
• 1392103-88-6 2-(4-chlorophenyl)-3-(4,5-dihydro-3-(4-methoxyphenyl)isoxazol-5-yl)-1H-indole 
• 282541-96-2 C₂₃H₁₅Cl₂NO 

Relevant articles and documents

Discovery of novel multi-substituted benzo-indole pyrazole schiff base derivatives with antibacterial activity targeting DNA gyrase

The design and synthesis of novel multi-substituted benzo-indole pyrazole Schiff base derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activities against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella. In addition, we selected 20 compounds for the in vitro antibacterial activities assay of 6 drug-resistant bacteria strains. The result revealed compound 8I-w exhibited excellent antibacterial activity against 4 drug-resistant E. coli bacteria strains with IC50 values of 7.0, 17.0, 13.5, and 1.0 μM, respectively. In vitro enzyme inhibitory assay showed that compound 8I-w displayed potent inhibition against DNA gyrase with IC50 values of 0.10 μM. The molecular docking model indicated that compounds 8I-w can bind well to the DNA gyrase by interacting with various amino acid residues. This study demonstrated that the compound 8I-w can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.

Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study

In this work, two novel series of indole-thiosemicarbazone derivatives were designed, synthesized, and evaluated for their cytotoxic activity against MCF-7, A-549, and Hep-G2 cell lines in comparison to etoposide and colchicine as the reference drugs. Generally, the synthesized compounds showed better cytotoxicity towards A-549 and Hep-G2 than MCF-7. Among them, (2E)-2-{[2-(4-chlorophenyl)-1H-indol-3-yl]methylidene}-N-(4-methoxyphenyl)hydrazinecarbothioamide (8l) was found to be the most potent compound against A-549 and Hep-G2, at least three times more potent than etoposide. The morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that compound 8l induced apoptosis in A-549 cells. Moreover, molecular docking methodology was exploited to elucidate the details of molecular interactions of the studied compounds with putative targets.

Green approach for the synthesis of 3-methyl-1-phenyl-4-((2-phenyl-1H-indol 3-yl)methylene)-1H-pyrazole-5(4H)-ones and their DNA Cleavage, antioxidant, and antimicrobial activities

3-Methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones (5a-i) was prepared by the condensation reaction of different 3-formyl-2-phenylindole derivatives (2a-i) and 3-methyl-1-phenyl-2-pyrazoline-5-one in quantitative yield by applying various green synthetic methods as grinding, microwave irradiation using different catalysts under solvent-free mild reaction conditions with high product yields. The structures of the synthesized compounds were characterized on the basis of elemental analysis, infrared, 1HNMR, 13C NMR, and mass spectral data. The synthesized compounds were screened for free radical scavenging, antimicrobial, and DNA cleavage activities. Most of the tested compounds belonging to the 3-methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones series exhibited promising activities.