- Iron-Catalyzed Oxidative Coupling of Indoline-2-ones with Aminobenzamides via Dual C-H Functionalization
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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.
- Lai, Yi-Huan,Wu, Run-Shi,Huang, Jie,Huang, Jun-Yu,Xu, Da-Zhen
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supporting information
p. 3825 - 3829
(2020/05/18)
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- 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
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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.
- Beloglazkina, Elena,Filatov, Vadim,Kukushkin, Maksim,Kuznetsova, Juliana,Majouga, Alexander,Skvortsov, Dmitry,Tafeenko, Viktor,Zyk, Nikolay
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p. 14122 - 14133
(2020/04/23)
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- Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
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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.
- Akaev, Andrey A.,Bezzubov, Stanislav I.,Desyatkin, Victor G.,Vorobyeva, Nataliya S.,Majouga, Alexander G.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
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p. 3340 - 3356
(2019/03/11)
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- Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones
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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
- 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
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p. 1849 - 1858
(2019/08/30)
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- Anti-leishmanial effect of spiro dihydroquinoline-oxindoles on volume regulation decrease and sterol biosynthesis of Leishmania braziliensis
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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
- Lea?ez, Jacques,Nu?ez, Jorge,García-Marchan, Yael,Sojo, Felipe,Arvelo, Francisco,Rodriguez, Daniel,Buscema, Ignacio,Alvarez-Aular, Alvaro,Serrano-Martín, Xenón
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- Microwave-assisted synthesis and evaluation of indole derivatives as potential anthelmintic agents
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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.
- Panda, Jnyanaranjan,Kumar, Anjan,Sahoo, Biswa Mohan,Banik, Bimal Krishna
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p. 1283 - 1288
(2020/06/27)
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- Leucine rich repeat kinase 2 (LRRK2) inhibitors based on indolinone scaffold: Potential pro-neurogenic agents
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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
- 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
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p. 328 - 342
(2017/07/07)
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- Solvent-free synthesis of oxovanadium (V) complexes with isatin base schiff ligands
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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.
- Mohammadi, Mohammad Kazem
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p. 1323 - 1327
(2017/09/07)
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- Aqueous single step synthesis and structural characterization of allylated, propargylated, and benzylated 3-substituted 3-aminooxindoles
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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
- Karpe, Sameer A.,Singh, Man,Chowhan, L. Raju
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supporting information
p. 1737 - 1746
(2017/09/23)
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- Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives
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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.
- Ma, Jian-Yin,Quan, Ying-Chun,Jin, Hong-Guo,Zhen, Xing-Hua,Zhang, Xue-Wu,Guan, Li-Ping
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p. 342 - 351
(2016/03/12)
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- Imidazolylpyridine-In(OTf)3 catalyzed enantioselective allylation of ketimines derived from isatins
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An enantioselective In(OTf)3-catalyzed allylation of ketimines derived from isatins in the presence of an imidazolylpyridine ligand is described. The reaction proceeded smoothly under mild conditions and resulted in 3-allyl 3-aminooxindoles with good yields and moderate to excellent enantioselectivities (up to 97% ee).
- Chen, Tingting,Cai, Chun
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supporting information
p. 5019 - 5022
(2016/06/14)
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- Tin powder-promoted one-pot synthesis of 3-spiro-fused or 3,3′-disubstituted 2-oxindoles
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A convenient and efficient method for the constructions of 3-spirooxindole derivatives or 3,3′-disubstituted oxindoles has been developed from one-pot reactions of isatins, hydrazides or aromatic amines, 2-(bromomethyl)acrylic ester and tin powder in the
- Wang, Juanjuan,Huang, Danfeng,Wang, Ke-Hu,Peng, Xiansha,Su, Yingpeng,Hu, Yulai,Fu, Ying
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supporting information
p. 9533 - 9542
(2016/10/22)
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- Solvatochromism of isatin based Schiff bases: An LSER and LFER study
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The derivatives of isatin (1H-indole-2,3-dione) have already been reported to show a variety of biological activities. However, there have hitherto been no reports on the solvatochromic effects of isatin derivatives, and it could be of interest to study a
- Brki?, Dominik R.,Bo?i?, Aleksandra R.,Nikoli?, Vesna D.,Marinkovi?, Aleksandar D.,Elshaflu, Hana,Nikoli?, Jasmina B.,Drmani?, Sa?a ?.
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p. 979 - 997
(2016/11/09)
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- METHOD OF USING AN INDOLINONE MOLECULE AND DERIVATIVES FOR INHIBITING LIVER FIBROSIS AND HEPATITIS
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This invention relates to methods of reversing and inhibiting liver fibrosis and hepatitis using a small indolinone molecule Hesperadin and related compounds. Methods of identifying such agents and using them to inhibit the expression of collagens and ECM
- -
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Paragraph 0277-0278; 0279-0280
(2015/02/25)
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- Synthesis of phenylcarbamic acid and 2-[2-oxo-3-(4-substituted phenylimino)-indolin-1-yl]acetohydrazide derivatives as promising antifungal agents
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Four phenylcarbamic acid methyl ester derivatives were prepared by oxidative transformation of isatin's Schiff bases (Baeyer-Villiger oxidation) under conventional heating as well as microwave irradiation. The ester derivatives were treated with hydrazine
- Al Marhoon, Zainab,Abdel-Megeed, Ahmed,Sholkamy, Essam N.,Siddiqui, M. Rafiq H.,El-Faham, Ayman
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p. 7665 - 7672
(2015/02/02)
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- Facile and highly diastereoselective synthesis of 3-aminooxindoles via AgOAc-catalyzed vinylogous Mannich reaction
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A novel AgOAc-catalyzed vinylogous Mannich reaction between easily prepared imines 1 derived from isatins and trimethylsilyloxyfuran 2 (TMSOF) was developed. This method provided a facile synthetic route to get access to synthetically useful quaternary 3-aminooxindole in excellent yields (94-99%) and diastereoselectivities (>99:1).
- Shi, Yu-Hua,Wang, Zheng,Shi, Ying,Deng, Wei-Ping
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experimental part
p. 3649 - 3653
(2012/06/18)
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- Synthesis and screening for antibacterial, analgesic and anti-inflammatory activity of Mannich bases derived from 1H-indole-2,3-dione
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The reaction of 1H-indole-2,3-dione) with substituted anilines in presence of acetic acid produces Schiff bases. Reaction of the Schiff bases with different secondary amines in presence of formaldehyde yields Mannich bases. The synthesized Mannich bases w
- Patro,Panda,Sahoo,Mishra,Panda
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p. 913 - 918
(2012/10/29)
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- 4-hydroxy-3-methoxyphenyl substituted 3-methyl-tetrahydroquinoline derivatives obtained through imino diels-alder reactions as potential antitumoral agents
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Two series of 17 tetrahydroquinoline compounds (2,4-DAr-THQs and DSQs), in which the 4-methoxy-3- hydroxyphenyl (isovanillin) structural unit is incorporated, were tested for their potential human tumor cell growth inhibitory effect on MCF-7, SKBR-3, PC3,
- Kouznetsov, Vladimir V.,Arenas, Diego R. Merchan,Arvelo, Francisco,Forero, Josue S. Bello,Sojo, Felipe,Munoz, Arturo
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scheme or table
p. 632 - 639
(2011/11/29)
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- Schiff bases of isatin: Inhibitory potential towards acetylcholinesterase and butyrylcholinesterase
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A series of different Schiff bases of isatin 1-20 was synthesized by the condensation of isatin with primary aromatic amines. It was observed that some of these compounds have the potential to inhibit acetylcholinesterase, whereas some others showed speci
- Khan, Khalid Mohammed,Mughal, Uzma Rasool,Ambreen, Nida,Rama, Nasim Hasan,Naz, Farzana,Perveen, Shahnaz,Choudhary, Muhammad Iqbal
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p. 716 - 720
(2013/01/09)
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- Microwave-Assisted, Solvent-Free Synthesis of 3′-(Aryl/Heteroaryl)-1- morpholinomethyl/piperidinomethylspiro[3H- Indole-3,2′-thiazolidine]-2, 4′(1H)-diones via 3-Isatinimines
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The solvent-free, microwave (MW)-assisted synthesis of a new series of 3′-(aryl/heteroaryl)-1-mor-pholinomethyl/piperidinomethylspiro[3H-indole- 3,2′-thiazolidine]-2,4′(1H)-diones has been achieved in an open vessel. Isatins 1 undergo an easy condensation
- Pandey, Manju,Raghuvanshi, Dushyant Singh,Singh, Krishna Nand
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experimental part
p. 49 - 53
(2009/06/18)
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- A simple entry to novel spiro dihydroquinoline-oxindoles using Povarov reaction between 3-N-aryliminoisatins and isoeugenol
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An easy, fast, and cheap way for the synthesis of the new 4′-(4-hydroxy-3-methoxyphenyl)-3′-methyl-3′,4′-dihydro-1′H-spiro[indoline-3,2′-quinolin]-2-ones using BF3 OEt2-promoted imino Diels-Alder cycloaddition between ketimine-isatin
- Kouznetsov, Vladimir V.,Bello Forero, Josué S.,Amado Torres, Diego F.
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experimental part
p. 5855 - 5857
(2009/04/05)
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- Synthesis, characterization and pharmacological screening of some isatinoid compounds
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Schiff bases and hydrazones of substituted isatins have been prepared by reacting isatin and the appropriate aromatic primary amine l hydrazines and characterized by spectral and elementary analysis. The compounds have been screened for analgesic, antiinflammatory and antipyretic activity. 3[(4-Bromo phenylidene)-1-amino] isatin is the only compound to exhibit all the activities. 3[(4-Bromo phenylidene)-1-amino] isatin and 3[(4- Bromo phenylidene)-1-amino]-5-methyl isatin possesses analgesic activity equipotent to paracetamol. 3(4-Phenylhydrazino) isatin and 3(thiosemicarbazino) isatin exhibit marked reduction of acetic acid induced inflammation. 3[(4-Methyl phenylidene)-1-amino] isatin at 200 mg/kg exhibits pronounced antipyretic activity comparable to paracetamol.
- Sridhar,Ramesh
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p. 668 - 672
(2007/10/03)
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- Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives
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Schiff bases and hydrazones of substituted isatins (1-28) were prepared by reacting isatin and aromatic primary amines/hydrazines. A new series of the corresponding N-Mannich base (29-35) was synthesised by reacting them with formaldehyde and diphenyl ami
- Sridhar, Seshaiah Krishnan,Saravanan, Muniyandy,Ramesh, Atmakuru
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p. 615 - 625
(2007/10/03)
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- Montmorillonite catalysed synthesis of novel spiro[3H-indole-3,3'-[3H- 1,2,4] triazol]-2(1H) ones in dry media under microwave irradiation
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A new route for the one pot synthesis of novel spiro[3H-indole-3,3'-[3H- 1,2,4] triazol]-2 (1H) ones utilizing 3-arylimino-2H-indol-2-ones (3) and thiosemicarbazide (4) as starting material under microwave irradiation is reported. Complete conversion was
- Dandia, Anshu,Sachdeva, Harshita,Devi, Ruby
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p. 272 - 275
(2007/10/03)
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- On antimicrobial activity of 3'-phenylspiro[3H-indole-3,2'-thiazolidine]-2,4' (1H)-diones
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3'-substituted phenylspiro[3H-indole-3,2'-thiazolidine]-2,4' (1H)-diones (1-15), tested toward Gram-positive, Gram-negative bacteria and Fungi, showed a significant activity against Gram-positive bacteria.
- Diurno,Mazzoni,Piscopo,Bolognese
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p. 435 - 441
(2007/10/02)
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- Synthesis of 2,4'-Dioxospiro-5'-acetic Acids: X-Ray Structure of 1-Benzyl-3'-(4-chlorophenyl)-2,4'-dioxospiro-5'-acetic Acid
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The title compounds have been prepared by the cyclocondensation of mercaptosuccinic acid with isatin-3-imines.The 1-benzyl derivatives have been synthesized by simultaneously reacting 1-benzylisatin, substituted anilines and mercaptosuccinic acid.The stru
- Popp, Frank D.,Rajopadhye Miland,Brown, David S.,Waddington, David,Uff, Barrie C.
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p. 261 - 265
(2007/10/02)
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- Synthesis of Spiro-2,4'(1H)-diones
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The title compounds have been prepared by the cyclocondensation of 3-mercaptopropanoic acid with isatin-3-imines.The 1-benzyl derivatives have been synthesized by simultaneously reacting 1-benzylisatin, substituted anilines and 3-mercaptopropanoic acid.Ma
- Rajopadhye, Milind,Popp, Frank D.
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- Reactions of 3-Arylimino-2-Indolinones with p-Substituted Phenylthiosemicarbazides
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3-Arylimino-2-indolinones (II) have been prepared by the condensation of isatins (I) with anilines.Reactions of II with p-substituted phenylthiosemicarbazides have resulted (in every instance) in the displacement of arylimino groups by the phenylthiosemic
- Varma, Rajendra S.,Garg, Pradeep K.
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p. 980 - 981
(2007/10/02)
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