70452-26-5

Usage

InChI:InChI=1/C17H15NO4/c1-22-12-8-6-11(7-9-12)15(19)10-17(21)13-4-2-3-5-14(13)18-16(17)20/h2-9,21H,10H2,1H3,(H,18,20)

Upstream product

• 91-56-5 indole-2,3-dione 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 62-53-3 aniline 
• 42366-35-8 hydroxyimino-N-phenylacetamide 

Downstream Products

• 66447-82-3 1,3-dihydro-3-[2-(4-methoxyphenyl)-2-oxoethylidene]indol-2(1H)-one 
• 56680-33-2 (E)-3-(2-(4-methoxyphenyl)-2-oxoethylidene)indolin-2-one 
• 51842-82-1 2-(4-methoxyphenyl)quinoline-4-carboxamide 
• 1252041-26-1 6'-(4-methoxyphenyl)-1'-phenyl-2'-thioxo-2',3'-dihydro-1'H-spiro[indoline-3,4'-pyrimidine]-2-one 
• 1622878-47-0 3-(4-methoxyphenyl)-9-acetyl-pyridazino[3,4-b]indole 
• 1296320-83-6 6-(4-methoxyphenyl)-5-(2-oxoindolin-3-yl)-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione 
• 1243024-37-4 6-(4-methoxyphenyl)-1,3-dimethyl-5-(2-oxoindolin-3-yl)-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione 
• 847-11-0 3-(4-methoxy-phenacyl)-indolin-2-one 
• 159862-03-0 (Z)-3-(2-(4-methoxyphenyl)-2-oxoethylidene)indolin-2-one 

Relevant academic research and scientific papers

Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with in Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds

An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindol

"on Water" Catalytic Aldol Reaction between Isatins and Acetophenones: Interfacial Hydrogen Bonding and Enamine Mechanism

"On water" catalytic aldol reaction catalyzed by polyetheramine (D230) has been developed for easy access to 3-substituted 3-hydroxyindolin-2-ones through the reaction between various substituted isatins and acetophenones/cyclic ketones in high yields under room temperature. Systematic mechanism investigation uncovers the secret for the on water catalytic aldol reaction: comparison of the heterogeneous and homogeneous reaction circumstances with yields of 95 and 20%, respectively, indicates the on-water reaction dominating; interfacial hydrogen bonding between isatin with H2O is tested based on the downfield shift of the C2 and C3's 13C NMR signals when water was added to the CDCl3 solution of isatin; Lewis base polyetheramine D230 catalyzes the aldol reaction via the enamine mechanism verified by in situ NMR and ESI-MS analysis.

Synthesis and biological evaluation of 3-substituted 2-oxindole derivatives as new glycogen synthase kinase 3β inhibitors

Glycogen synthase kinase 3β (GSK-3β) is a widely investigated molecular target for numerous diseases including Alzheimer's disease, cancer, and diabetes mellitus. Inhibition of GSK-3β activity has become an attractive approach for treatment of diabetes and cancer. We report the discovery of novel GSK-3β inhibitors of 3-arylidene-2-oxindole scaffold with promising activity. The most potent compound 3a inhibits GSK-3β with IC50 4.19 nM. In a cell-based assay 3a shows no significant leucocyte toxicity at 10 μM and is moderately cytotoxic against A549 cells. Compound 3a demonstrated high antidiabetic efficacy in obese streptozotocin-treated rats improving glucose tolerance at a dose of 50 mg/kg body weight thus representing an interesting lead for further optimization.

Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds

Molecular hybridization is considered as an effective tactic to develop drugs for the treatment of cancer. A series of novel hybrid compounds of isatin and Michael acceptor were designed and synthesized on the basis of association principle. These hybrid compounds were tested for cytotoxic potential against human cancer cell lines namely, BGC-823, SGC-7901 and NCI-H460 by MTT assay. Most compounds showed good anti-growth activities in all tested human cancer cells. SAR and QSAR analysis may provide vital information for the future development of novel anti-cancer inhibitors. Notably, compound 6a showed potent growth inhibition on BGC-823, SGC-7901 and NCI-H460 with the IC50 values of 3.6 ± 0.6, 5.7 ± 1.2, 3.2 ± 0.7 μM, respectively. Besides, colony formation assays, wound healing assays and flow cytometry analysis indicated 6a exhibited a potent anti-growth and anti-migration ability in a concentration-dependence manner through arrested cells in the G2/M phase of cell cycle. Moreover, 6a significantly repressed tumor growth in a NCI-H460 xenograft mouse model. Overall, our findings suggested isatin analogues inspired Michael acceptor may provide promising lead compounds for the development of cancer chemotherapeutics.

An efficient and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3-hydroxyindolin-2-ones

A simple and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3-hydroxyindolines in presence of ammonium acetate is described. The developed protocol also allows synthesis of the carboxamide moeity directly from isatin a

DABCO-catalyzed synthesis of 3-substituted-3-hydroxyindolin-2-ones in aqueous media

An efficient and greener protocol for easy access to 3-susbstituted-3-hydroxy-2-oxindoles by the reaction with various substituted isatins and acetophenones is described. This protocol is widely applicable for a variety of isatins and acetophenones using

Corrosion inhibition effect of spiropyrimidinethiones on mild steel in 15% HCl solution: Insight from electrochemical and quantum studies

The effect of synthesized spiropyrimidinethiones, namely, 6′-(4-methoxyphenyl)-1′-phenyl-2′-thioxo-2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyrimidine]-2-one (MPTS) and 6′-(4-methoxyphenyl)-1′-phenyl-2′-thioxo-2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyrimidine

Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

Libraries of spiro[cyclopropane-1,3′-indolin]-2′-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer),

Synthesis and structure-activity relationship studies of small molecule disruptors of EWS-FLI1 interactions in Ewing's sarcoma

EWS-FLI1 is an oncogenic fusion protein implicated in the development of Ewing's sarcoma family tumors (ESFT). Using our previously reported lead compound 2 (YK-4-279), we designed and synthesized a focused library of analogues. The functional inhibition of the analogues was measured by an EWS-FLI1/NR0B1 reporter luciferase assay and a paired cell screening approach measuring effects on growth inhibition for human cells containing EWS-FLI1 (TC32 and TC71) and control PANC1 cell lines devoid of the oncoprotein. Our data revealed that substitution of electron donating groups at the para-position on the phenyl ring was the most favorable for inhibition of EWS-FLI1 by analogs of 2. Compound 9u (with a dimethylamino substitution) was the most active inhibitor with GI50 = 0.26 ± 0.1 μM. Further, a correlation of growth inhibition (EWS-FLI1 expressing TC32 cells) and the luciferase reporter activity was established (R2 = 0.84). Finally, we designed and synthesized a biotinylated analogue and determined the binding affinity for recombinant EWS-FLI1 (Kd = 4.8 ± 2.6 μM).

Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.