1217-83-0

Usage

Uses

Used in Organic Synthesis:
2-(4-Chlorophenyl)-1H-indole-3-carbaldehyde is used as a building block in organic synthesis for the creation of heterocyclic compounds. Its unique structure allows for the formation of various complex organic molecules that are valuable in different chemical applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(4-Chlorophenyl)-1H-indole-3-carbaldehyde serves as a key intermediate. It is utilized in the development of pharmaceuticals, taking advantage of its potential biological activities to contribute to the therapeutic effects of new drugs.
Used in Drug Development:
2-(4-Chlorophenyl)-1H-indole-3-carbaldehyde is employed in the development of drugs for various therapeutic purposes. Its pharmacological properties make it a promising candidate for the treatment of a range of conditions, pending further research and development in medicinal applications.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, 2-(4-Chlorophenyl)-1H-indole-3-carbaldehyde is used as a precursor for the synthesis of new drug molecules. Its role in creating bioactive compounds is crucial for advancing the discovery and innovation of novel therapeutic agents.
Each of these applications underscores the versatility and importance of 2-(4-Chlorophenyl)-1H-indole-3-carbaldehyde in the realms of chemical and medicinal research, as well as in the development of new pharmaceuticals.

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

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

Downstream Products

• 82327-15-9 [1-[2-(4-Chloro-phenyl)-1H-indol-3-yl]-meth-(Z)-ylidene]-(4-morpholin-4-yl-phenyl)-amine 
• 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 
• 1228017-20-6 C₂₃H₁₄ClNO₄ 

Relevant academic research and scientific papers

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.

Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives

Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630?μM, comparable to the standard ascorbic acid (0.655?μM).

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.

Preparation of some novel imidazopyridine derivatives of indole as anticancer agents: one-pot multicomponent synthesis, biological evaluation and docking studies

A series of novel imidazopyridine derivatives of indole has been synthesized. All the synthesized derivatives were evaluated for their antiproliferative activity against A-549, T-47D, Hep-G2 and MCF-7 human cancer cell lines. The results demonstrated that some of these derivatives exhibited moderate to excellent cytotoxic activities. Compounds 7a having a cyclohexyl ring substituted to the second amine of imidazopyridyl moiety and phenyl ring of the C-2 indole ring and 7f with a para-methylphenyl ring at the same position exhibited the highest activity against the A-594 cell line with IC50 of 11.48?μM and 10.66?μM, respectively. The results indicate that compounds 7a and 7f are more cytotoxic towards cancer cell lines compared with etoposide in vitro. In addition, compounds, 7d and 7j showed the most potent activity against Hep-G2, equal to etoposide as the standard drug. Also, most of the compounds were inactive against the T-47D and MCF-7 cell lines. The morphological analysis by the acridine orange/ethidium bromide double-staining test and flow cytometry analysis indicated that compounds 7a and 7f induced apoptosis in A-549 cells. Furthermore, in silico and in vitro results of the synthesized compounds showed good correlation with each other. Molecular docking results of the compounds of the 7a–k series with the cyclohexyl ring substituted to the second amine of the imidazopyridyl moiety compared with the 7l–t members with the t-butyl group at the same position confirmed the effect of the higher lipophilicity on hydrophobic interactions with the studied enzymes. Moreover, all the compounds showed higher affinity to tubulin than topoisomerase IIα enzyme.

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.

Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes

A new method for synthesizing 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed intramolecular electrophilic amination of 2-arylindole-3-carbaldehyde O-acetyl oximes was developed.

Chiral Phosphoric Acid Catalyzed Intramolecular Dearomative Michael Addition of Indoles to Enones

An enantioselective intramolecular dearomative Michael addition of indolyl enones is presented. In the presence of catalytic amount of chiral phosphoric acid, various enantioenriched spiro-indolenines bearing a quaternary stereogenic center were obtained

Synthesis and biological evaluation of novel indolyl isoxazoline derivatives as analgesic and antiinflammatory agents

A series of 3-(2-(4-substituted phenyl)-1H-indol-3-yl)-1-(4-substituted phenyl)prop-2-en-1-one 3(a-l) were synthesized from substituted indole aldehydes. Using hydroxylamine hydrochloride the chalcones 3(a-l) were cyclized to afford a novel series of 2-(4-substituted phenyl)-3-(3-(4-substituted phenyl)-4,5-dihydroisoxazol-5-yl)-1H-indole 4(a-l). The structure of all these compounds were established on the basis of spectral (IR, 1H NMR) studies. The compounds 4(a-l) were evaluated for the antiinflammatory and analgesic activity by using different pharmacological models. The most active compounds were subjected to acute ulcerogenesis activity and were found to be less ulcerogenic than the reference drug indomethacin.

Microwave-Assisted synthesis of 30-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity

A new series of indole-based chromene derivatives 4a-4p has been synthesized by one pot cyclocondensation reaction of 2-phenyl-1H-indole-3- carbaldehyde 1a-1h; malononitrile 2; and 1,3-cyclohexanedione/dimedone 3a/b under microwave irradiation catalyzed by an organocatalyst 4-(N,N-dimethylamino) pyridine. Easy experimental procedure, high yield, selectivity, and shorter reaction time are the imperative features of this method. All the compounds were screened against a representative panel of bacteria and fungi. Some of the compounds are found to be equipotent or more potent than that of standard drugs as evident from SAR study. Springer Science+Business Media, LLC 2011.

Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: Hit to lead studies

A series of benzofuran-3-one indole phosphatidylinositol-3-kinases (PI3K) inhibitors identified via HTS has been prepared. The optimized inhibitors possess single digit nanomolar activity against p110α (PI3K-α), good pharmaceutical properties, selectivity versus p110γ (PI3K-γ), and tunable selectivity versus the mammalian target of rapamycin (mTOR). Modeling of compounds 9 and 32 in homology models of PI3K-α and mTOR supports the proposed rationale for selectivity. Compounds show activity in multiple cellular proliferation assays with signaling through the PI3K pathway confirmed via phospho-Akt inhibition in PC-3 cells.