29551-52-8

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 91-56-5 indole-2,3-dione 
• 1243657-66-0 1,3-diethyl 2-(2-bromophenylamino)-2-oxoethylphosphonate 
• 152302-94-8 N-(2-Iodophenyl)-α-(diethoxyphosphinyl)acetamide 
• 59-48-3 2-oxoindole 
• 104-86-9 4-chlorobenzylamine 

Downstream Products

• 131609-35-3 3-(4-chlorobenzyl)-1,3-dihydroindol-2-one 
• 1416008-68-8 tert-butyl 4'-(4-chlorophenyl)-2-oxo-2',5'-diphenyl-2',4'-dihydrospiro[indoline-3,3'-pyrazole]-1-carboxylate 
• 1279108-50-7 (E)-tert-butyl 3-(4-chlorobenzylidene)-2-oxoindoline-1-carboxylate 
• 29551-51-7 3-(4-chlorobenzylidene)-1,3-dihydroindol-2-one 

Relevant academic research and scientific papers

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

Gif-2209, an oxindole derivative, accelerates melanogenesis and melanosome secretion via the modification of lysosomes in b16f10 mouse melanoma cells

Melanogenesis and melanosome secretion are regulated by several mechanisms. In this study, we found that the oxindole derivative GIF-2209 accelerated melanogenesis associated with the discrimination in the expression and intracellular distributions of two

3-aryl-indolinones derivatives as antiplasmodial agents: synthesis, biological activity and computational analysis

Malaria is an infectious illness, affecting vulnerable populations in Third World countries. Inspired by natural products, indole alkaloids have been used as a nucleus to design new antimalarial drugs. So, eighteen oxindole derivatives, aza analogues were obtained with moderate to excellent yields. Also, the saturated derivatives of oxindole and aza derivatives via H2/Pd/C reduction were obtained in good yields, leading to racemic mixtures of each compound. Next, the inhibitory activity against P. falciparum of 18 compounds were tested, founding six compounds with IC50 20 μM. The most active of these compounds was 8c; however, their unsaturated derivative 7c was inactive. Then, a structure-activity relationship analysis was done, founding that focused LUMO lobe on the specific molecular zone is related to inhibitory activity against P. falciparum. Finally, we found a potential inhibition of lactate dehydrogenase by oxindole derivatives, using molecular docking virtual screening.

Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines

A novel synthetic route for the construction of (E)-3-alkylideneindolin-2-ones through iron-catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self-condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3-alkylideneindolin-2-one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.

Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst

We report herein that a commercially available CeO2 is an active and reusable catalyst for the C3-selective alkenylation of oxindole with aldehydes under solvent-free conditions. This catalytic method is generally applicable to different aromatic and aliphatic aldehydes, giving 3-alkyledene-oxindoles in high yields (87%–99%) and high stereoselectivities (79%–93% to E-isomers). This is the first example of the catalytic synthesis of 3-alkenyl-oxindoles from oxindole and various aliphatic aldehydes. The Lewis acid-base interaction between Lewis acid sites on CeO2 and benzaldehyde was studied by in situ IR. The structure-activity relationship study using CeO2 catalysts with different sizes suggests that defect-free CeO2 surface is the active site for this reaction.

Piers-rubinsztajn reaction and the application in siloxane/polysiloxane chemistry

An efficient synthesis of biologically important benzylidene-indolin-2-one derivatives using meglumine as green catalyst and ethanol:water as reaction media at 78°C has been developed. The effects of reaction conditions such as solvents, temperature, and amount of catalyst were investigated. The present methodology offers many advantages such as simple procedure, less time taking to complete the reaction, high yield of products, and clean reaction profile.

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

Solvent-free synthesis of novel spirocyclic oxindole derivatives via a Michael-aldol cascade by grinding

A simple and novel synthesis of spirocyclic oxindole derivatives by the reaction of (E)-3-arylideneindole-2-ones and 1,4-dithiane-2,5-diol via a Michael-aldol cascade under solvent-free reaction conditions is reported. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4′,5′-dihydro-2′H-spiro[oxindole-3,3′-thiophen]-2-ones in moderate to good yields. The structures of all the products were characterised by NMR, infrared spectroscopy and HRMS.

Advanced palladium free approach to the synthesis of substituted alkene oxindoles: Via aluminum-promoted Knoevenagel reaction

A synthetic route for the synthesis of C24, as well as for the design of focused libraries of direct AMPK activators was developed based on a convergent strategy. The proposed scheme corresponds to the current trends in C-H bond functionalization. The use of aluminum isopropoxide for the Knoevenagel condensation of oxindole with benzophenones is a noticeable point of this work.

Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare

In our continued efforts to improve the potential utility of the α-methylene-γ-lactone scaffold, 62 new and 59 known natural α-methylenelactam analogues including α-methylene-γ-lactams, α-arylidene-γ and δ-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the α-methylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50?=?10.4?μM but less cytotoxic activity with IC50?=?141.2?μM (against HepG2 cell line) and 161.2?μM (against human hepatic L02?cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C.?orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structure–activity relationships revealed that incorporation of the aryl group into the α-exo-methylene and the N-benzyl substitution increased the activity. Meanwhile, the α-arylidene-γ-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N-benzyl substituted α-(2-fluorophenyl)-γ-lactam was identified as the most promising natural-based scaffold for further discovering and developing improved crop-protection agents.