64264-45-5Relevant academic research and scientific papers
Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst
Rashed, Md. Nurnobi,Touchy, Abeda Sultana,Chaudhari, Chandan,Jeon, Jaewan,Siddiki, S.M.A. Hakim,Toyao, Takashi,Shimizu, Ken-ichi
, p. 970 - 976 (2020/01/31)
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.
Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines
Gopalaiah, Kovuru,Tiwari, Ankit
, p. 7229 - 7237 (2020/12/01)
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.
Synthesis and biological evaluation of 3-substituted 2-oxindole derivatives as new glycogen synthase kinase 3β inhibitors
Lozinskaya, Natalia A.,Babkov, Denis A.,Zaryanova, Ekaterina V.,Bezsonova, Elena N.,Efremov, Alexander M.,Tsymlyakov, Michael D.,Anikina, Lada V.,Zakharyascheva, Olga Yu.,Borisov, Alexander V.,Perfilova, Valentina N.,Tyurenkov, Ivan N.,Proskurnina, Marina V.,Spasov, Alexander A.
, p. 1804 - 1817 (2019/03/23)
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.
Piers-rubinsztajn reaction and the application in siloxane/polysiloxane chemistry
Patel, Chetananda,Kumar, Amit,Patil, Pooja,Sharma, Abha
supporting information, p. 600 - 605 (2019/08/08)
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.
Investigation of triazole-linked indole and oxindole glycoconjugates as potential anticancer agents: Novel Akt/PKB signaling pathway inhibitors
Nagarsenkar, Atulya,Prajapti, Santosh Kumar,Guggilapu, Sravanthi Devi,Birineni, Swetha,Sravanti Kotapalli, Sudha,Ummanni, Ramesh,Babu, Bathini Nagendra
supporting information, p. 646 - 653 (2016/05/19)
In continuation of our venture towards the synthesis of novel bioactive agents, two sets of triazole-linked glycoconjugates were synthesized from indole/oxindole (29 compounds) and were further characterized by IR (infrared spectroscopy), 1H NM
Tandem Horner-Wadsworth-Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: The synthesis of Semaxanib and GW441756
Lubkoll, Jana,Millemaggi, Alessia,Perry, Alexis,Taylor, Richard J.K.
experimental part, p. 6606 - 6612 (2010/10/19)
A tandem sequence involving Horner-Wadsworth-Emmons (HWE) olefination followed by a palladium-catalysed intramolecular Heck reaction has been developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability of the process has been established by carrying out one-pot syntheses of Semaxanib, an angiogenesis signalling inhibitor, and GW441756, an aza-oxindole Trk A inhibitor.
Seven 3-methyl-idene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib
Spencer, John,Chowdhry, Babur Z.,Hamid, Samiyah,Mendham, Andrew P.,Male, Louise,Coles, Simon J.,Hursthouse, Michael B.
experimental part, p. o71-o78 (2010/06/20)
The solid-state structures of a series of seven substituted 3-methyl-idene-1H-indol-2(3H)-one derivatives have been determined by single-crystal X-ray diffraction and are compared in detail. Six of the structures {(3Z)-3-(1H-pyrrol-2-ylmethyl-idene)-1H-in
Synthesis and biological evaluations of 3-substituted indolin-2-ones: A novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases
Sun, Li,Tran, Ngoc,Tang, Flora,App, Harald,Hirth, Peter,McMahon, Gerald,Tang, Cho
, p. 2588 - 2603 (2007/10/03)
3-Substituted indolin-2-ones have been designed and synthesized as a novel class of tyrosine kinase inhibitors which exhibit selectivity toward different receptor tyrosine kinases (RTKs). These compounds have been evaluated for their relative inhibitory properties against a panel of RTKs in intact cells. By modifying the 3-substituted indolin-2-ones, we have identified compounds which showed selective inhibition of the ligand- dependent autophosphorylation of various RTKs at submicromolar levels in cells. Structure-activity analysis for these compounds and their relative potency and selectivity to inhibit particular RTKs has determined that (1) 3- [(five-membered heteroaryl ring)methylidenyl]indolin-2-ones are highly specific against the VEGF (Flk-1) RTK activity, (2) 3-(substituted benzylidenyl)indolin-2-ones containing bulky group(s) in the phenyl ring at the C-3 position of indolin-2-ones showed high selectivity toward the EGF and Her-2 RTKs, and (3) the compound containing an extended side chain at the C- 3 position of the indolin-2-one (16) exhibited high potency and selectivity when tested against the PDGF and VEGF (Flk-1) RTKs. Recent published crystallographic data for two of these 3-substituted indolin-2-ones provides a rationale to suggest that these compounds may bind in the ATP binding pocket of RTKs. The structure-activity analysis supports the use of subsets of these compounds as specific chemical leads for the development of RTK- specific drugs with broad application for the treatment of human diseases.
