33829-00-4Relevant articles and documents
Iron-Catalyzed Oxidative Coupling of Indoline-2-ones with Aminobenzamides via Dual C-H Functionalization
Lai, Yi-Huan,Wu, Run-Shi,Huang, Jie,Huang, Jun-Yu,Xu, Da-Zhen
supporting information, p. 3825 - 3829 (2020/05/18)
We describe an unprecedented dual C-H functionalization of indolin-2-one via an oxidative C(sp3)-H/N-H/X-H (X = N, C, S) cross-coupling protocol, which is catalyzed by a simple iron salt under mild and ligand-free conditions and employs air (molecular oxygen) as the terminal oxidant. This method is readily applicable for the construction of tetrasubstituted carbon centers from methylenes and provides a wide variety of spiro N-heterocyclic oxindoles.
Synthesis of 1,3-diaryl-spiro[azetidine-2,3′-indoline]-2′,4-diones: Via the Staudinger reaction: Cis - Or trans -diastereoselectivity with different addition modes
Beloglazkina, Elena,Filatov, Vadim,Kukushkin, Maksim,Kuznetsova, Juliana,Majouga, Alexander,Skvortsov, Dmitry,Tafeenko, Viktor,Zyk, Nikolay
, p. 14122 - 14133 (2020/04/23)
A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2,3′-indoline]-2′,4-diones was developed based on Staudinger ketene-imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2,3′-indoline]-2′,4-diones were synthesized using this method. For comparison, the same compounds were obtained using a known technique, where ketene is generated from pre-synthesized acyl chloride. It was shown that the use of oxalyl chloride for ketene generation in the one-pot reaction at room temperature allows for the reversal of the diastereoselectivity of spiro-lactam formation, unlike previously described procedures.
Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones
Mathebula, Bakolise,Butsi, Kamogelo Rosinah,van Zyl, Robyn Lynne,Jansen van Vuuren, Natasha Colleen,Hoppe, Heinrich Carl,Michael, Joseph Philip,de Koning, Charles Bernard,Rousseau, Amanda Louise
, p. 1849 - 1858 (2019/08/30)
A series of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones were prepared by the inverse-electron-demand aza-Diels–Alder reaction (Povarov reaction) of imines derived from isatin and substituted anilines, and the electron-rich alkenes trans-isoeuge
Anti-leishmanial effect of spiro dihydroquinoline-oxindoles on volume regulation decrease and sterol biosynthesis of Leishmania braziliensis
Lea?ez, Jacques,Nu?ez, Jorge,García-Marchan, Yael,Sojo, Felipe,Arvelo, Francisco,Rodriguez, Daniel,Buscema, Ignacio,Alvarez-Aular, Alvaro,Serrano-Martín, Xenón
, p. 31 - 38 (2019/02/15)
Diverse spiro dihydroquinoline-oxindoles (JS series) were prepared using the BF3?OEt2-catalyzed imino Diels-Alder reaction between ketimine-isatin derivatives and trans-isoeugenol. Ten spiro-oxiindole derivatives were selected and ev
Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
Akaev, Andrey A.,Bezzubov, Stanislav I.,Desyatkin, Victor G.,Vorobyeva, Nataliya S.,Majouga, Alexander G.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 3340 - 3356 (2019/03/11)
A novel stereocontrolled assembly of spiro[oxindole-3,2′-pyrrolidines] via [3+2]-cycloaddition of donor-acceptor cyclopropanes to electron-poor ketimines, iminooxindoles, was developed. The method allows for efficient employment of common readily available donor-acceptor cyclopropanes, functionalized with ester, keto, nitro, cyano etc. groups, and N-unprotected iminooxindoles. The stereospecificity of the initial SN2-like imine attack on a cyclopropane molecule together with a high diastereoselectivity of further C-C bond formation facilitate a rapid access to spiro[oxindole-3,2′-pyrrolidines] in their optically active forms. Preliminary in vitro testing of the synthesized compounds against LNCaP (p53+) and PC-3 (p53-) cells revealed good antiproliferative activities and p53-selectivity indices for several compounds that are intriguing in terms of their further investigation as inhibitors of MDM2-p53 interaction.
Microwave-assisted synthesis and evaluation of indole derivatives as potential anthelmintic agents
Panda, Jnyanaranjan,Kumar, Anjan,Sahoo, Biswa Mohan,Banik, Bimal Krishna
, p. 1283 - 1288 (2020/06/27)
An efficient method is developed and exploited for the synthesis of indole derivatives via microwave-assisted technology. By considering the advantage microwave synthesis in terms of high efficient energy, indole derivatives are prepared. In the current study, the Schiff's bases are first synthesized by reaction of 1H-indole-2,3-dione (isatin) with various substituted anilines in presence of acetic acid under microwave irradiation. Then the Mannich bases are produced by condensation of Schiff bases with different secondary amines in the presence of formaldehyde. The newly synthesized compounds are characterized by TLC report and spectral data followed by evaluation for anthelmintic activity against Pheretima posthuma. Albendazole is used as standard drug for comparative study. The titled compounds are screened for anthelmintic activity at the concentration of 10, 20 and 50 mg/ml. The anthelmintic effect of standard drug Albendazole is also evaluated at 10 mg/ml. The results of present study indicate that some of the tested compounds exhibit significant anthelmintic activity in dose dependent manner.
Solvent-free synthesis of oxovanadium (V) complexes with isatin base schiff ligands
Mohammadi, Mohammad Kazem
, p. 1323 - 1327 (2017/09/07)
Isatin and its analog are versatile substrates which acts as a precursor for a large number of pharmacologically active compounds, thus having a significant importance in the synthesis of different heterocyclic compounds. This article aims to synthesize the new monooxovanadium(V) complexes with isatin Schiff bases as a ligand. All new compounds structures are characterized and confirmed with spectra analyses.
Aqueous single step synthesis and structural characterization of allylated, propargylated, and benzylated 3-substituted 3-aminooxindoles
Karpe, Sameer A.,Singh, Man,Chowhan, L. Raju
supporting information, p. 1737 - 1746 (2017/09/23)
Efficient zinc-mediated allylation, propargylation, and benzylation of isatin-derived imines were undertaken for the synthesis of 3-substituted 3-aminooxindoles with ≈80% yield. Such alternative approach has efficiently avoided the use of catalysts, sever
Leucine rich repeat kinase 2 (LRRK2) inhibitors based on indolinone scaffold: Potential pro-neurogenic agents
Salado, Irene G.,Zaldivar-Diez, Josefa,Sebastian, Victor,Li, Lingling,Geiger, Larissa,González, Silvia,Campillo, Nuria E.,Gil, Carmen,Morales, Aixa V.,Perez, Daniel I.,Martinez, Ana
, p. 328 - 342 (2017/07/07)
Leucine-rich repeat kinase 2 (LRRK2) is one of the most pursued targets for Parkinson's disease (PD) therapy. Moreover, it has recently described its role in regulating Wnt signaling and thus, it may be involved in adult neurogenesis. This new hypothesis
Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives
Ma, Jian-Yin,Quan, Ying-Chun,Jin, Hong-Guo,Zhen, Xing-Hua,Zhang, Xue-Wu,Guan, Li-Ping
, p. 342 - 351 (2016/03/12)
Herein, a series of 3-phenyliminoindolin-2-one derivatives were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. The IR spectra of the compounds afforded NH stretching (3340-3346 cm-1) bands and C=O stretching (1731-1746 cm-1). In the 1H-NMR spectra of the compounds, N-H protons of indoline ring were observed at 10.65-10.89 ppm generally as broad bands, and 13C-NMR spectra of the compounds C=O were seen at 161.72-169.27 ppm. Interestingly, compounds 3o, 3p and 3r significantly shortened immobility time in the The forced swimming test (FST) and The tail suspension test (TST) at 50 mg/kg dose levels. In addition, compound 3r exhibited higher levels of efficacy than the reference standard fluoxetine but had no effect on locomotor activity in the open-field test. Compound 3r significantly increased serotonin and norepinephrine and the metabolite 5-hydroxyindoleacetic acid in mouse brain, suggesting that the effects of compound 3r may be mediated through these neurotransmitters. In the seizure screen, 15 compounds showed some degree against PTZ-induced seizure at a dose of 100 mg/kg, and the tested compounds did not show any neurotoxicity at a dose of 300 mg/kg in the rotarod test.
