151409-79-9

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule. In this case, the compound has 17 carbon (C) atoms, 15 hydrogen (H) atoms, 1 nitrogen (N) atom, and 1 oxygen (O) atom.

Explanation

This structure describes the arrangement of atoms and the type of chemical bonds between them. It is an aldehyde derivative of indole, which is a heterocyclic aromatic organic compound.

Explanation

The compound contains an aldehyde group (-CHO), an indole ring, and a methylphenyl group (-C6H4-CH3) attached to the indole.

Explanation

The indole ring in the molecule is aromatic, meaning it has a planar structure with delocalized π-electrons, which contributes to its stability and unique chemical properties.

Explanation

The compound is used as a starting material or intermediate in the synthesis of other organic compounds, particularly in the pharmaceutical and chemical industries.

Explanation

Due to its unique chemical structure and properties, the compound has potential applications in the field of organic chemistry and drug discovery. It can also be used in various other industries, making it a versatile and important chemical compound.

Explanation

The solubility of the compound in different solvents is not mentioned in the material provided. However, it is generally expected to be soluble in organic solvents like ethanol, methanol, or acetone, and less soluble in water.

Explanation

The stability of the compound under various conditions (e.g., temperature, pH, light exposure) is not mentioned in the material provided. However, as an aromatic compound, it is generally expected to be stable under normal conditions.

Explanation

The reactivity of the compound with other chemicals or functional groups is not mentioned in the material provided. However, the presence of the aldehyde group suggests that it may be reactive with reducing agents, oxidizing agents, and nucleophiles.

Chemical Structure

1-[(4-METHYLPHENYL)METHYL]-1H-INDOLE-3-CARBALDEHYDE

Functional Groups

Aldehyde, Indole, and Methylphenyl

Aromaticity

Hetrocyclic aromatic compound

Pharmaceutical and Chemical Industries

Synthesis of various organic compounds and building block in drug production

Applications

Organic chemistry, drug discovery, and potential uses in different industries

InChI:InChI=1/C17H15NO/c1-13-6-8-14(9-7-13)10-18-11-15(12-19)16-4-2-3-5-17(16)18/h2-9,11-12H,10H2,1H3

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 104-81-4 4-Methylbenzyl bromide 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 1207733-72-9 C₂₁H₂₀N₄O 
• 1207615-72-2 (Z)-5-((1-(4-methylbenzyl)-1H-indol-3-yl)methylene)imidazolidine-2,4-dione 
• 1376446-96-6 (E)-3-(1-(4-methylbenzyl)-1H-indol-3-yl)acrylic acid 
• 799824-69-4 C₂₃H₂₁N₃O₃ 
• 1399879-54-9 (E)-4,4'-(6-(2-((1-(4-methylbenzyl)-1H-indol-3-yl)methylene)hydrazinyl)-1,3,5-triazine-2,4-diyl)dimorpholine 
• 664317-83-3 1-[(4-methylphenyl)methyl]-1H-indole-3-methanol 
• 1054644-81-3 (3aS,4S,6R,6aR)-2,2-Dimethyl-6-(6-{2-[1-(4-methyl-benzyl)-1H-indol-3-yl]-ethylamino}-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid cyclopropylamide 
• 151410-01-4 2-[1-(4-Methyl-benzyl)-1H-indol-3-yl]-ethylamine 

Relevant academic research and scientific papers

Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones

Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two

Molecular dynamics guided development of indole based dual inhibitors of EGFR (T790M) and c-MET

Secondary acquired mutation in EGFR, i.e. EGFR T790M and amplification of c-MET form the two key components of resistant NSCLC. Thus, previously published pharmacophore models of EGFR T790M and c-MET were utilized to screen an in-house database. On the ba

Design, synthesis and biological evaluation of matrine derivatives as potential anticancer agents

Using matrine (1) as the lead compound, a series of new 14-(N-substituted-2-pyrrolemethylene) matrine and 14-(N-substituted-indolemethylene) matrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H NMR, 13C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity against three human cancer cell lines (SMMC-7721, A549 and CNE2). The results revealed that compound A6 and B21 displayed the most significant anticancer activity against three cancer cell lines with IC50 values in range of 3.42–8.05 μM, which showed better activity than the parent compound (Matrine) and positive control Cisplatin. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound A6 and B21 could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. The cell cycle analysis also revealed that compound A6 could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase.

Identification of low micromolar dual inhibitors for aldose reductase (ALR2) and poly (ADP-ribose) polymerase (PARP-1) using structure based design approach

Clinical studies have revealed that diabetic retinopathy is a multifactorial disorder. Moreover, studies also suggest that ALR2 and PARP-1 co-occur in retinal cells, making them appropriate targets for the treatment of diabetic retinopathy. To find the dual inhibitors of ALR2 and PARP-1, the structure based design was carried out in parallel for both the target proteins. A series of novel thiazolidine-2,4-dione (TZD) derivatives were therefore rationally designed, synthesized and their in vitro inhibitory activities against ALR2 and PARP-1 were evaluated. The experimental results showed that compounds 5b and 5f, with 2-chloro and 4-fluoro substitutions, showed biochemical activities in micromolar and submicromolar range (IC50 1.34–5.03?μM) against both the targeted enzymes. The structure-activity relationship elucidated for these novel inhibitors against both the enzymes provide new insight into the binding mode of the inhibitors to the active sites of enzymes. The positive results of the biochemical assay suggest that these compounds may be further optimized and utilized for the treatment of diabetic retinopathy.

Structure-based design of new poly (ADP-ribose) polymerase (PARP-1) inhibitors

Poly (ADP-ribose) polymerase (PARP-1) is a well-established nuclear protein with prominent role in signaling and DNA repair. Various clinical candidates have been identified with the role in PARP-1 inhibition. Based on the pharmacophoric features identified from previous studies and molecular docking interactions, thiazolidine-2,4-dione derivatives have been evaluated for their PARP inhibitory activity. From an in vitro assay, 5-((1-(4-isopropylbenzyl)-1H-indol-3-yl)methylene)thiazolidine-2,4-dione (16) was identified as a potent inhibitor having low micromolar inhibitory activity (IC50=0.74±0.25μM). Thus, a structure-based design approach utilized in the present study helped to identify thiazolidine-2,4-dione as a novel scaffold against PARP-1 for potential development of potent anticancer therapeutics.

Anti-cardiac-failure compound, preparation method and application thereof

The invention discloses an anti-cardiac-failure compound, a preparation method thereof and an application of the compound in the cardiac failure treatment. The provided preparation method has the advantages of simple and easy process, less by-products, ea

[...] -containing heterocyclic structure and preparation and application of compound miazines

The invention belongs to the field of chemic synthesis and relates to a heterocyclopyrimidine compound containing an aryl hydrazone structure, as well as a stereomer and pharmaceutically acceptable salt, hydrate, solvate or prodrug of the heterocyclopyrim

Synthesis and anti-proliferative activity of aromatic substituted 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H) -trione analogs against human tumor cell lines

Based on previous SAR studies on N-benzylindole and barbituric acid hybrid molecules, we have synthesized a series of aromatic substituted 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H) -trione analogs (3a-i) and evaluated th

Synthesis and antimycobacterial activity of novel thiadiazolylhydrazones of 1-substituted indole-3-carboxaldehydes

A series of novel thiocarbohydrazones of substituted indoles and their corresponding thiadiazole derivatives were prepared, and their structures were confirmed by different analytical and spectroscopic methods. The derivatives were prepared by a sequential synthetic strategy including substitution at N-1 position of indole ring by various aliphatic and benzylic substituents, followed by condensation with thiocarbohydrazide, and finally cyclization by triethyl orthoformate. The derivatives were tested for their antimycobacterial activity against Mycobacterium bovis BCG, and the results revealed that among the synthesized compounds, thiadiazole derivatives 4e, 4f, 4n, 4p, 4q, and 4t exhibited the highest activity with IC50 value of 3.91 μg/mL. The results indicate that the thiadiazole moiety plays a vital role in exerting antimycobacterial activity. A series of indole-based thiadiazole derivatives with various substitutions at N-1 position of indole ring have been synthesized and tested for their antimycobacterial activity. Compounds 4e (R = butyl), 4f (R = pentyl), 4n (R = 4-fluorobenzyl), 4p (R = 4-chlorobenzyl), 4q (R = 4-bromobenzyl) and 4t (R = 4-methoxybenzyl) were the most potent derivatives with IC50 value of 3.91 μg/mL.

Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4- morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents

A series of 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their cytotoxic activities against five cancer cell lines. Most of them exhibited moderate to significant cytotoxic activities and high-selectivity against one or more cell lines, and nearly all of them had higher potency than positive controls against MDA-MB-231 cell line. The most promising compound 15f showed strong cytotoxic activities against H460, HT-29 and MDA-MB-231 cell lines, which were 1.7- to 66.5-folds more active than 2-(1H-Indazol-4-yl)-6-((4-(methylsulfonyl)-1-piperazinyl)methyl)-4-(4- morpholinyl)thieno[3,2-d]pyrimidine(GDC-0941). To investigate the SARs of thieno[3,2-d]pyrimidine derivatives in more details, CoMFA (q2 = 0.436, r2 = 0.937) and CoMSIA (q2 = 0.706, r2 = 0.947) models on H460 cell line were established. The generated 3D-QSAR models can be used for further rational design of novel thienopyrimidines as highly potent and selective cytotoxic agents.