76195-80-7

Usage

Chemical structure

1H-Indole-3-carboxaldehyde, 2-(4-methoxyphenyl)consists of an indole ring with a carboxaldehyde and a 4-methoxyphenyl group attached.

Usage

Commonly used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and dyes.

Biological activities

Studied for its potential anti-cancer, anti-inflammatory, and antimicrobial properties.

Optoelectronic applications

Investigated for its potential use in organic light-emitting diodes (OLEDs) and other optoelectronic devices due to its fluorescent properties.

Industry applications

Versatile applications in both the pharmaceutical and materials science industries.

Upstream product

• 5784-95-2 2-(4-methoxyphenyl)-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 62-53-3 aniline 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 100-97-0 hexamethylenetetramine 
• 157869-15-3 2-((4-methoxyphenyl)ethynyl)aniline 
• 1616706-98-9 N-benzyl-2-((4-methoxyphenyl)ethynyl)aniline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 107-02-8 acrolein 
• 24310-46-1 4-methoxyacetophenone phenylhydrazone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 82327-14-8 [1-[2-(4-Methoxy-phenyl)-1H-indol-3-yl]-meth-(Z)-ylidene]-(4-morpholin-4-yl-phenyl)-amine 
• 126479-68-3 4-{[1-[2-(4-Methoxy-phenyl)-1H-indol-3-yl]-meth-(Z)-ylidene]-amino}-N,N-diphenyl-benzamide 
• 76699-13-3 (E)-1-(4-Chloro-phenyl)-3-[2-(4-methoxy-phenyl)-1H-indol-3-yl]-propenone 
• 76699-12-2 (E)-3-[2-(4-Methoxy-phenyl)-1H-indol-3-yl]-1-(4-nitro-phenyl)-propenone 
• 71654-74-5 3-[5-(4-Chloro-phenyl)-2-(4-nitro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-2-(4-methoxy-phenyl)-1H-indole 
• 71491-06-0 3-[5-(4-Chloro-phenyl)-2-(2,4-dinitro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-2-(4-methoxy-phenyl)-1H-indole 
• 126479-72-9 3-Chloro-4-[2-(4-methoxy-phenyl)-1H-indol-3-yl]-1-(4-morpholin-4-yl-phenyl)-azetidin-2-one 
• 126479-79-6 3-(2-Chloro-phenoxy)-4-[2-(4-methoxy-phenyl)-1H-indol-3-yl]-1-(4-morpholin-4-yl-phenyl)-azetidin-2-one 
• 126479-76-3 4-{3-Chloro-2-[2-(4-methoxy-phenyl)-1H-indol-3-yl]-4-oxo-azetidin-1-yl}-N,N-diphenyl-benzamide 
• 126479-83-2 4-{3-(2-Chloro-phenoxy)-2-[2-(4-methoxy-phenyl)-1H-indol-3-yl]-4-oxo-azetidin-1-yl}-N,N-diphenyl-benzamide 
• 920514-61-0 {[2-(4-methoxyphenyl)-1H-indol-3-yl]methylene}malononitrile 
• 1351939-84-8 2-amino-4-(2-(4-methoxyphenyl)-1H-indol-3-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1351939-86-0 2-amino-4-(2-(4-methoxyphenyl)-1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 

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.

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.

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3

A variety of structurally novel polycyclic sulfonyl indolines have been synthesized via FeCl2-catalyzed or UV-driven intramolecular formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methyl)propiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.

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.

Method for microwave-assisted preparation of 2-phenyl-3-formylindole compound

The invention discloses a method for microwave-assisted preparation of a 2-phenyl-3-formylindole compound. The method comprises: carrying out a complete reaction on an aniline compound, acrolein and abrominated benzene compound by using an organic solvent

A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles

In this paper, a copper(ii)-catalyzed reaction of o-alkynylanilines with dimethylformamide (DMF) in the presence of oxygen has been developed for synthesizing multisubstituted 3-formyl indole scaffolds. This one-pot reaction proceeds through a cascade 5-endo-dig cyclization followed by formylation to construct 1,2-disubstituted 3-formyl indoles. The key aspects of this synthesis method are the broad substrate scope (with 38 examples), and well tolerating various functional groups. In addition, a detailed mechanism has been proposed, where DMF may serve as a carbon source for the in situ C3 formylation of the obtained indole derivatives.

Design and synthesis of bis(indolyl)ketohydrazide-hydrazones: Identification of potent and selective novel tubulin inhibitors

A novel series of ketohydrazide-hydrazones as analogues of naturally occurring coscinamides has been synthesized and evaluated for their anticancer activity against five cancer cell lines. Of the twenty-synthesized ketohydrazide-hydrazones, compounds, 21c, 21f, 21g, 21k and 21o showed cytotoxic effects (less than 50% cell survival) against multiple cancer cell lines when tested at a final concentration of 10?μM. IC50 of three compounds 21f, 21k and 21o was determined to be less than 5?μM for all tested cancer cell lines. Compound 21k exhibited significant anticancer activity against MCF-7, MDA-MB-231, HCT-116 and JURKAT cancer cell lines with IC50 values of 0.8?μM, 0.50?μM, 0.15?μM, and 0.22?μM, respectively. Also, 21k was found to be more selectively cytotoxic against tumor cells when compared to normal cells. Preliminary mechanism of action studies indicated that the most active compound 21k induced caspase-dependent apoptosis in cells. 21k arrests cell cycle in G2/M phase by inhibiting of tubulin polymerization (IC50?=?0.6?μM).