3476-86-6

Upstream product

• 59-48-3 2-oxoindole 
• 459-57-4 4-fluorobenzaldehyde 
• 91-56-5 indole-2,3-dione 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 34203-08-2 (E)-3-(4-fluorobenzylidene)-1-methylindolin-2-one 
• 34203-09-3 (Z)-3-(4-fluorobenzylidene)-1-methylindolin-2-one 
• 90828-17-4 (Z)-3-[(4-fluorophenyl)methylidene]-1,3-dihydro-2H-indol-2-one 
• 1250954-17-6 C₂₅H₂₀BrFN₂O₃ 

Relevant academic research and scientific papers

Chalcone scaffolds as photofunctional hybrid material of indolin-2-one-functionalized siloxy framework for optical sensing of Cu2+

Owing to their easy approachability and high degree of structural and functional diversity, many multicomponent reactions such as 1,3-dipolar cycloaddition have been a rich source of conjugated π-systems, functionalised chromophores and active molecules. Despite their high potential for investigation and practical benefits, few products have thus far been scrutinized for their metal sensing abilities. In the present study, indolin-2-one chalcones bearing siloxy molecular systems were synthesized by a [2+3] cycloaddition-based reaction sequence. A designed chemosensor exhibited an optical (absorption spectra) response toward Cu2+ ions in an acetonitrile solution. Different aspects of the sensing phenomena such as selectivity and association constants were studied in detail using UV-vis spectroscopy. The calibration plot was linear (R2 = 0.9966) over a large range of Cu2+ ion concentrations (10 μM). This novel effort has initiated a well-organized method for the efficient improvement of cation sensors with triazole for detecting heavy metal pollutants in environmental and healthcare fields on a large scale.

New cell cycle checkpoint pathways regulators with 2-Oxo-indoline scaffold as potential anticancer agents: Design, synthesis, biological activities and in silico studies

3-Arylidene-2-oxo-indoline derivatives are at the heart of a wide range of clinically, medicinally and biologically important compounds among the 2-oxo-indolines. A number of 3-arylidene-2-oxo-indolines have been approved for clinical application. Accordi

Discovery of novel indolin-2-one compounds as potent inhibitors of HsClpP for cancer treatment

Human caseinolytic protease proteolytic subunit (HsClpP) is a highly conserved serine protease that plays an essential role in cell homeostasis through removal of the damaged and/or misfolded proteins. Recently, due to its critical role in cancer prolifer

Inversion kinetics of someE/Z3-(benzylidene)-2-oxo-indoline derivatives and theirin silicoCDK2 docking studies

The structure-based design of some CDK2 inhibitors with a 3-(benzylidene)indolin-2-one scaffold as potential anticancer agents was realized. Target compounds were obtained asE/Zmixtures and were resolved to correspondingE- andZ-diastereomers.In silicostudies using MOE 2019.01 software revealed better docking on the targeted enzyme for theZ-diastereomer compared to theE-one. A time-dependent kinetic isomerization study was carried out for the inversion ofE/Zdiastereomers in DMSO-d6at room temperature, and were found to obey the first order kinetic reactions. Furthermore, a determination of the kinetic inter-conversion rate order by graphical analysis method and calculation of the rate constant and half-life of this kinetic process were carried out. For the prediction of the stability of the diastereomer(s), a good multiple regression equation was generated between the reaction rates of isomerization and some QM parameters with significantpvalue.

A facile synthesis of novel polycyclic spiropyrrolidine oxindoles incorporating the 1,3-dipolar cycloaddition of azomethine ylides

This study describes the synthesis of novel polycyclic spiropyrrolidine oxindoles through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ with 3-(arylmethylene)-indolin-2-ones. Effect of substituents of azomethine ylides and various d

Microfluidic Visible-Light Paternò–Büchi Reaction of Oxindole Enol Ethers

A novel microfluidic visible-light process for the functionalisation of oxindoles is reported. The chemistry is based on the reactivity of the corresponding enol ethers, which participate in a site-, regio- and diastereoselective [2+2] heterocycloaddition (Paternò–Büchi) process. The mild reaction conditions, the use of available ketones, together with the high generality (23 examples) and robustness (up to gram scale) make this process a useful synthetic platform for the construction of structurally strained heterocycles.

Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

An enantioselective hetero-Diels-Alder reaction of alkylidene oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N, N ′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spirooxindole class of small molecules. exo -Cycloadducts formed via stereospecific cycloaddition with Z -olefin displayed potent activity in modulation of hedgehog pathway.

Macrocyclic Modalities Combining Peptide Epitopes and Natural Product Fragments

"Hot loop" protein segments have variable structure and conformation and contribute crucially to protein-protein interactions. We describe a new hot loop mimicking modality, termed PepNats, in which natural product (NP)-inspired structures are incorporated as conformation-determining and-restricting structural elements into macrocyclic hot loop-derived peptides. Macrocyclic PepNats representing hot loops of inducible nitric oxide synthase (iNOS) and human agouti-related protein (AGRP) were synthesized on solid support employing macrocyclization by imine formation and subsequent stereoselective 1,3-dipolar cycloaddition as key steps. PepNats derived from the iNOS DINNN hot loop and the AGRP RFF hot spot sequence yielded novel and potent ligands of the SPRY domain-containing SOCS box protein 2 (SPSB2) that binds to iNOS, and selective ligands for AGRP-binding melanocortin (MC) receptors. NP-inspired fragment absolute configuration determines the conformation of the peptide part responsible for binding. These results demonstrate that combination of NP-inspired scaffolds with peptidic epitopes enables identification of novel hot loop mimics with conformationally constrained and biologically relevant structure.

Combined Scaffold Evaluation and Systems-Level Transcriptome-Based Analysis for Accelerated Lead Optimization Reveals Ribosomal Targeting Spirooxindole Cyclopropanes

With evolutionary drug resistance impacting efforts to treat disease, the need for small molecules that exhibit novel molecular mechanisms of action is paramount. In this study, we combined scaffold-directed synthesis with a hybrid experimental and transc

Photoredox asymmetric catalytic enantioconvergent substitution of 3-chlorooxindoles

An enantioconvergent substitution of 3-substituted 3-chlorooxindoles with N-aryl glycines under visible light irradiation is reported. A transition-metal-free cooperative catalysis platform with a dicyanopyrazine-derived chromophore (DPZ) as a photoredox catalyst and a chiral Br?nsted acid catalyst is effective for these transformations, which involve a single-electron transfer redox step and an enantioselective radical coupling. A variety of valuable chiral 3-aminomethylene-3-substituted oxindoles can be directly synthesized with high yields and enantioselectivities.