25365-71-3

Basic information

• Product Name: 2-PHENYLINDOLE-3-CARBOXALDEHYDE
• Synonyms: OTAVA-BB BB7214110035;AURORA 23280;ART-CHEM-BB B023284;2-PHENYLINDOLE-3-ALDEHYDE;2-PHENYLINDOLE-3-CARBOXALDEHYDE;2-PHENYL-1H-INDOLE-3-CARBALDEHYDE;3-FORMYL-2-PHENYL-INDOLE;AKOS SVR00140
• CAS NO: 25365-71-3
• Molecular Formula: C₁₅H₁₁NO
• Molecular Weight: 221.25
• Product Categories: Indoles and derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 25365-71-3.mol

Chemical Properties

• Melting Point: 249-253 °C(lit.)
• Boiling Point: 462.9 °C at 760 mmHg
• Flash Point: 237.5 °C
• Appearance: /
• Density: 1.237 g/cm³
• Vapor Pressure: 9.47E-09mmHg at 25°C
• Refractive Index: 1.709
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 15.30±0.30(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2-PHENYLINDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLINDOLE-3-CARBOXALDEHYDE(25365-71-3)
• EPA Substance Registry System: 2-PHENYLINDOLE-3-CARBOXALDEHYDE(25365-71-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 25365-71-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used as a reactant for the preparation of various bioactive compounds, making it a valuable building block in drug discovery and development.
As Tryptophan Dioxygenase Inhibitors:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used as a reactant for the synthesis of pyridyl-ethenyl-indoles, which are potential anticancer immunomodulators. These compounds can modulate the immune response and exhibit anticancer properties.
As Antimicrobial Agents:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the preparation of pyrimidinones via the Biginelli reaction. These compounds exhibit antimicrobial activity, making them useful in the development of new antibiotics.
As Antiinflammatory Agents and Analgesics:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of [(phenyl)pyrazolyl]indole derivatives, which possess antiinflammatory and analgesic properties. These compounds can be used in the treatment of inflammation and pain.
As Antimicrobial and Antioxidant Agents:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the preparation of indole thiophene chalcones via Claisen-Schmidt condensation. These chalcones exhibit both antimicrobial and antioxidant activities, making them potential candidates for use in pharmaceutical and cosmetic products.
As PI3K Inhibitors:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of benzofuranone attached indole derivatives, which act as PI3K inhibitors. These compounds can be used in the development of targeted cancer therapies.
As Novel Antiandrogens:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the preparation of ionone-based chalcones, which have been found to possess antiandrogen properties. These compounds can be used in the treatment of prostate cancer and other androgen-dependent conditions.
As Antiinflammatory Agents for Edema:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of oxazolylindoles, which exhibit antiinflammatory properties and can be used in the treatment of edema and other inflammatory conditions.

InChI:InChI=1/C15H11NO/c17-10-13-12-8-4-5-9-14(12)16-15(13)11-6-2-1-3-7-11/h1-10,16H

Upstream product

• 948-65-2 2-phenyl-indole 
• 67-66-3 chloroform 
• 93-61-8 N-methyl-N-phenylformamide 
• 14300-21-1 2-phenylbenzo[d][1,3]oxazepine 
• 64-17-5 ethanol 
• 143360-89-8 o-(phenylethynyl)trifluoroacetanilide 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 1262057-02-2 (E)-1-((2-(phenylethynyl)phenyl)diazenyl)piperidine 
• 100-97-0 hexamethylenetetramine 
• 64-19-7 acetic acid 
• 4660-96-2 N,N-dimethyl-1-(2-phenyl-1H-indol-3-yl)methanamine 
• 59-48-3 2-oxoindole 
• 5059-30-3 2-chloroindole-3-carboxaldehyde 
• 98-80-6 phenylboronic acid 

Downstream Products

• 138469-55-3 2-{[1-(2-Phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenol 
• 142677-04-1 1-benzyl-2-phenyl-1H-indole-3-carbaldehyde 
• 120607-82-1 [(2-phenyl-1H-indol-3-y)lmethylene]malononitrile 
• 1392103-82-0 3-[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]-2-phenyl-1H-indole 
• 263892-02-0 3-[3-(4-bromophenyl)-4,5-dihydroisoxazol-5-yl]-2-phenyl-1H-indole 
• 1392103-83-1 3-[4,5-dihydro-3-(4-methoxyphenyl)isoxazol-5-yl]-2-phenyl-1H-indole 
• 596807-63-5 C₂₄H₁₉NO₂ 
• 1416038-47-5 4-((1H-indol-3-yl)(5-methyl-2-phenyl-1H-indol-3-yl)methyl)-3-methyl-1H-pyrazol-5(4H)-one 
• 1416038-48-6 4-((5-chloro-2-phenyl-1H-indol-3-yl)(1H-indol-3-yl)methyl)-3-methyl-1H-pyrazol-5(4H)-one 
• 1416038-49-7 4-((1H-indol-3-yl)(5-methoxy-2-phenyl-1Hindol-3-yl)methyl)-3-methyl-1H-pyrazol-5(4H)-one 
• 5460-84-4 2-phenyl-1H-indole-3-carbaldehyde oxime 
• 76869-08-4 3-ethoxymethyl-2-phenyl-indole 
• 127302-21-0 4-[1-(4-Methoxy-phenyl)-5-(2-phenyl-1H-indol-3-yl)-4,5-dihydro-1H-pyrazol-3-yl]-phenylamine 
• 127302-11-8 3-(2-Methoxy-phenylamino)-1-(4-{[1-(2-phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-propan-1-one 

Relevant articles and documents

An Efficient, Eco-Friendly Synthesis of Pyran Annulated Indole Analogs under Conventional Heating and Microwave Irradiation, and Their Anticancer and Antioxidant Activity

A rapid, facile, green, eco-friendly, cost effective, and efficient method for the synthesis of pyran annulated indole analogs via one-pot, three components reaction is developed. According to the developed method 2,5-disubstituted-1H-indol-3-carboxaldehyde, malononitrile and various phenols react under MW assisted solvent-free conditions. These compounds can be also prepared under a conventional method that is characterized by some disadvantages in comparison with the above approach. Structures of products are confirmed by FT-IR, 1H and 13C NMR, and mass spectral data. The in vitro antioxidant and cytotoxic activities of the products are evaluated against three tumor cell lines and discussed in terms of structure―activity analysis. Among the screened compounds 3d, 4a, 4b, 5a, and 5b exhibit excellent antioxidant activity. Compounds 4b, 5a, and 5b demonstrate strong cytotoxic activity.

A CONVENIENT SYNTHETIC METHOD OF 2-SUBSTITUTED INDOLES AND ITS APPLICATION FOR THE SYNTHESIS OF NATURAL ALKALOID, BORRERINE

A simple synthetic method of 2-substituted indoles is developed.Total synthesis of natural alkaloid, borrerine, is also reported

C3-Formylation of Indoles in Continuous Flow

We have developed a continuous flow C3-formylation technique for indoles using hexamethylenetetramine (HMTA) and iodine. A mixed solvent system of DMF–H2O (1:1, vol/vol) completely dissolves reagents and prevents clogging of microchannels during fluid flow. The continuous flow technique provides maximized mixing and excellent heat transfer efficiency. Thus, flow chemistry accelerates the rate of C3-formylation of indoles in the absence of a strong acid, base, or metal catalyst. We show that high yields of C3-formylated indoles (up to 83%) can be obtained at 150°C when the residence time is as low as 8 min.

Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes

The oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved by employing molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The important reaction of C3 formylation of free NH and substituted indoles containing various substituents is accomplished from the corresponding Mannich bases. This methodology can also be extended for the synthesis of aryl and other heteroaryl aldehydes and ketones. Furthermore, the usefulness of the method is successfully demonstrated on a gram scale.

Investigation of indole functionalized pyrazoles and oxadiazoles as anti-inflammatory agents: Synthesis, in-vivo, in-vitro and in-silico analysis

There are several potential side and adverse effects are found to be associated with the anti-inflammatory drugs in clinical practice. The long-term use of these clinical agents highly unsafe. It encouraged the development of novel heterocyclic compounds with potential anti-inflammatory activity and low to no toxicity. In present investigation, a total of 12 indole functionalized pyrazole and oxadiazole derivatives were designed, synthesized and evaluated for the in-vivo anti-inflammatory and analgesic potential. These compounds displayed comparable anti-inflammatory and analgesic potential to the reference drugs. Finally, molecular docking analysis was performed considering different anti-inflammatory targets to determine the mechanistic target of the designed molecules. Detailed analysis suggested that the molecules inhibit COX-2, preferably over other anti-inflammatory targets. The results suggested that two compounds (15c and 15f) were found promising candidates for the development of novel anti-inflammatory agents.

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.COPYRIGHT KIPO 2020

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.

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

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).