79183-26-9

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-METHYLBENZYL)-1H-INDOLE-2,3-DIONE is used as a chemical precursor for the synthesis of various pharmaceuticals and natural products, due to its ability to be incorporated into complex molecular structures, enhancing the development of new therapeutic agents.
Used in Organic Chemistry:
1-(4-METHYLBENZYL)-1H-INDOLE-2,3-DIONE is used as a key intermediate in organic synthesis for creating a range of chemical compounds, leveraging its reactivity and structural properties to facilitate the formation of diverse organic molecules.
Used in Drug Discovery:
1-(4-METHYLBENZYL)-1H-INDOLE-2,3-DIONE is utilized as a lead compound in drug discovery, owing to its potential anti-inflammatory, anti-cancer, and anti-viral properties, which make it a promising candidate for the development of novel therapeutics.
Used as a Fluorescent Dye:
1-(4-METHYLBENZYL)-1H-INDOLE-2,3-DIONE is employed as a fluorescent dye in various applications, capitalizing on its optical properties to serve in imaging and detection processes.
Used in the Production of Synthetic Indigo:
1-(4-METHYLBENZYL)-1H-INDOLE-2,3-DIONE is used in the manufacturing process of synthetic indigo, a significant blue dye, due to its role in the chemical reactions that produce this pigment.

InChI:InChI=1/C16H13NO2/c1-11-6-8-12(9-7-11)10-17-14-5-3-2-4-13(14)15(18)16(17)19/h2-9H,10H2,1H3

Upstream product

• 104-81-4 4-Methylbenzyl bromide 
• 91-56-5 indole-2,3-dione 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 1443437-36-2 1-(4-methylbenzyl)-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one 
• 1509929-33-2 (S)-3-allyl-3-hydroxy-1-(4-methylbenzyl)indolin-2-one 
• 1621419-51-9 C₄₀H₄₃N₃O₄ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of isatin derivatives containing 1,3,4-thiadiazole as potent a-glucosidase inhibitors

A series of (Z)-3-(2-(1,3,4-thiadiazol-2-yl)hydrazono)-1-substituted indolin-2-ones derivatives (3a-3m) were designed and synthesized. All newly synthesized compounds were evaluated for their a-glucosidase inhibitory activity with resveratrol as positive control in vitro. Except for 3i and 3j, all of the compounds showed a potent inhibitory activity against a-glucosidase with IC50 values in the range of 3.12 ± 1.25 to 45.95 ± 1.26 μM and the purity of these compounds was greater than 95%. The IC50 values were being compared to the standard resveratrol (IC50 = 22.00 ± 1.15 μM) and it was found that compounds 3b, 3d-3h were found to be more active than resveratrol. Specifically, (Z)-3-(2-(1,3,4-thiadiazol-2-yl)hydrazono)-1-(4-chlorobenzyl)indolin-2-one (3d) exhibited the most potent a-glucosidase inhibitory activity with IC50 value of 3.12 ± 1.25 μM. The kinetic analysis revealed that compound (3d) is noncompetitive inhibitor. Structure activity relationship has been established for all compounds. Furthermore, the binding interactions of compound 3d with the active site of a-glucosidase were confirmed through molecular docking. This study has identified a new class of potent a-glucosidase inhibitors for further investigation.

NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates

An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.

Novel Multitarget Directed Triazinoindole Derivatives as Anti-Alzheimer Agents

The multifaceted nature of Alzheimer's disease (AD) demands treatment with multitarget-directed ligands (MTDLs) to confront the key pathological aberrations. A novel series of triazinoindole derivatives were designed and synthesized. In vitro studies revealed that all the compounds showed moderate to good anticholinesterase activity; the most active compound 23e showed an IC50 value of 0.56 ± 0.02 μM for AChE and an IC50 value of 1.17 ± 0.09 μM for BuChE. These derivatives are also endowed with potent antioxidant activity. To understand the plausible binding mode of the compound 23e, molecular docking studies and molecular dynamics simulation studies were performed, and the results indicated significant interactions of 23e within the active sites of AChE as well as BuChE. Compound 23e successfully diminished H2O2-induced oxidative stress in SH-SY5Y cells and displayed excellent neuroprotective activity against H2O2 as well as Aβ-induced toxicity in SH-SY5Y cells in a concentration dependent manner. Furthermore, it did not show any significant toxicity in neuronal SH-SY5Y cells in the cytotoxicity assay. Compound 23e did not show any acute toxicity in rats at doses up to 2000 mg/kg, and it significantly reversed scopolamine-induced memory deficit in mice model. Additionally, compound 23e showed notable in silico ADMET properties. Taken collectively, these findings project compound 23e as a potential balanced MTDL in the evolution process of novel anti-AD drugs.

Synthesis, spectroscopic characterization and antimicrobial potential of certain new isatin-indole molecular hybrids

Molecular hybridization has a wide application in medicinal chemistry to obtain new biologically active compounds. New isatin-indole molecular hybrids 5a-n have been synthesized and characterized by various spectroscopic tools. The in vitro antimicrobial potential of the prepared compounds 5a-n was assessed using diameter of the inhibition zone (DIZ) and minimum inhibitory concentration (MIC) assays against a panel of Gram-negative bacteria, Gram-positive bacteria and fungi. Most of the synthesized compounds 5a-n showed weak activities against Gram-negative bacteria while compounds 5b and 5c exhibited good activities against Gram-positive bacteria. On the other hand, compound 5j emerged as the most active compound towards Candida albicans (C. albicans), with an MIC value of 3.9 μg/mL, and compound 5g as the most active congener towards Asperagillus Niger (A. Niger), with an MIC value of 15.6 μg/mL. Moreover, compound 5h manifested the best anti-P. notatum effect, with an MIC value of 7.8 μg/mL, making it equipotent with compound 5g.

Electrocatalytic C-H/N-H Coupling of 2′-Aminoacetophenones for the Synthesis of Isatins

2′-Aminoacetophenones undergo a C(sp3)-H oxidation followed by intramolecular C-N bond formation by virtue of a simple electrochemical oxidation in the presence of n-Bu4NI, providing various isatins with moderate to good yields. The reaction intermediates were detected, and a radical-based pathway was proposed.

PTEN INHIBITORS

The therapeutic use of inhibitors of PTEN activity in the treatment of PTEN-mediated diseases, conditions, and injuries is disclosed.