42407-86-3

Usage

InChI:InChI=1/C15H12N2O/c1-10-6-8-11(9-7-10)16-14-12-4-2-3-5-13(12)17-15(14)18/h2-9H,1H3,(H,16,17,18)

Upstream product

• 64-17-5 ethanol 
• 91-56-5 indole-2,3-dione 
• 106-49-0 p-toluidine 
• 62-53-3 aniline 
• 42366-35-8 hydroxyimino-N-phenylacetamide 

Downstream Products

• 111259-64-4 3'-(4-methylphenyl)-2,4'-dioxospiro-5'-acetic acid 
• 138590-16-6 3-Phenylsulfanyl-3-p-tolylamino-1,3-dihydro-indol-2-one 
• 97693-01-1 3-(2-Oxo-3-p-tolylamino-2,3-dihydro-1H-indol-3-ylsulfanyl)-propionic acid 
• 79560-73-9 N-(4’-tolyl)-2-(2-oxoindoline-3-ylidene)hydrazinecarbothioamide 
• 141857-88-7 C₂₂H₁₆N₂O₂S 
• 141857-91-2 2-Methyl-6-(2-oxo-2,3-dihydro-1H-indol-3-yloxy)-benzoic acid 
• 1087-99-6 3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Syntheses, spectroscopy, tautomerism, induced chirality and molecular structure of 3-(o/p-tolylimino)indolin-2-one and bis[3-(o/p-tolylimino)indole-2-olato-κ2N,O]-Δ/Λ-zinc(II)

The isatin-Schiff bases 3-(o/p-tolylimino)indolin-2-one (HL1 and HL2) undergo tautomerization from lactam (L)- to enol (E)-form in solution, which in turn reacts with zinc(II) nitrate to give bis[3-(o/p-tolylimino)indole-2-olato-κ2N,O]-Δ/Λ-zinc

Experimental and theoretical studies on isatin-Schiff bases and their copper(II)-complexes: Syntheses, spectroscopy, tautomerism, redox potentials, EPR, PXRD and DFT/TDDFT

The isatin-Schiff bases 3-(o/p-tolylimino)indolin-2-one (HL1 and HL2) react with the copper(II) acetate or nitrate to give the bis[3-(o/p-tolylimino)indole-2-olato-κ2N,O]copper(II) (1 and 2) via lactam (L)- to enol (E)-tautomerism in solution.

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

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.

Anti-leishmanial effect of spiro dihydroquinoline-oxindoles on volume regulation decrease and sterol biosynthesis of Leishmania braziliensis

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

Design, synthesis and biological activity of novel tacrine-isatin Schiff base hybrid derivatives

A series of novel tacrine-isatin Schiff base hybrid derivatives (7a-p)were designed, synthesized and evaluated as multi-target candidates against Alzheimer's disease (AD). The biological assays indicated that most of these compounds displayed potent inhibitory activity toward acetylcholinesterase (AChE)and butyrylcholinesterase (BuChE)and specific selectivity for AChE over BuChE. It was also found that they act as excellent metal chelators. The compounds 7k and 7m were found to be good inhibitors of AChE-induced amyloid-beta (Aβ)aggregation. Most of the compounds inhibited AChE with the IC50 values, ranging from 0.42 nM to 79.66 nM. Amongst them, 7k, 7m and 7p, all with a 6 carbon linker between tacrine and isatin Schiff base exhibited the strongest inhibitory activity against AChE with IC50 values of 0.42 nM, 0.62 nM and 0.95 nM, respectively. They were 92-, 62- and 41-fold more active than tacrine (IC50 = 38.72 nM)toward AChE. Most of the compounds also showed a potent BuChE inhibition among which 7d with an IC50 value of 0.11 nM for BuChE is the most potent one (56-fold more potent than that of tacrine (IC50 = 6.21 nM)). In addition, most compounds exhibited the highest metal chelating property. Kinetic and molecular modeling studies revealed that 7k is a mixed-type inhibitor, capable of binding to catalytic and peripheral site of AChE. Our findings make this hybrid scaffold an excellent candidate to modify current drugs in treating Alzheimer's disease (AD).

Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]

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.

Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones

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

Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives

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.

Imidazolylpyridine-In(OTf)3 catalyzed enantioselective allylation of ketimines derived from isatins

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).

Synthesis of 3′,4′-Diaryl-4′H-spiro[indoline-3,5′-[1′,2′,4′]oxadiazol]-2-ones via DMAP-catalyzed Domino Reactions and Their Antibacterial Activity

A convenient and metal-free DMAP-catalyzed domino reaction of isatins, arylamines and hydroximoyl chlorides has been developed to achieve 1,3-dipolar cycloaddition of imines into aryl nitrile oxides at ambient temperature. In this one-pot transformation,