33829-01-5

Upstream product

• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 91-56-5 indole-2,3-dione 
• 615-36-1 2-bromoaniline 

Downstream Products

• 1149390-43-1 3-allyl-3-((2-bromophenyl)amino)indolin-2-one 
• 1259925-22-8 11-benzyl-9,9a-dihydro-6H-dibenzo[e,g]pyrido[1,2-a][1,4]diazocin-10(11H)-one 
• 1259925-20-6 7,8-diallyl-5-benzyl-7,8-dihydrodibenzo[e,g][1,4]diazocin-6(5H)-one 
• 1412900-56-1 (E)-3-((2-bromophenyl)amino)-3-(3-(4-(trifluoromethoxy)phenyl)allyl)indolin-2-one 
• 1412900-57-2 (E)-3-(3-(3-((2-bromophenyl)amino)-2-oxoindolin-3-yl)prop-1-en-1-yl)-4-fluorobenzonitrile 
• 1412900-55-0 (E)-4-(3-(3-((2-bromophenyl)-amino)-2-oxoindolin-3-yl)prop-1-en-1-yl)benzonitrile 
• 1259925-10-4 (E)-3-((2-bromophenyl)amino)-3-(3-(3-methoxyphenyl)allyl)indolin-2-one 
• 1259925-11-5 (E)-3-((2-bromophenyl)amino)-3-(3-(4-methoxyphenyl)allyl)indolin-2-one 
• 339079-00-4 [Pr(C₆H₄NCOCNC₆H₄Br)3] 
• 339078-99-8 [La(C₆H₄NCOCNC₆H₄Br)3] 

Relevant academic research and scientific papers

Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1

Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.

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.

Solvatochromism of isatin based Schiff bases: An LSER and LFER study

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

Novel synthesis and functionalization of ortho-ortho disubstituted biphenyls and a highly condensed novel heterocycle using radical cyclization reaction

This paper describes a novel synthetic route for the preparation of ortho-ortho disubstituted biphenyls and compounds possessing highly condensed ring system represented by structures X and Y, respectively. Several approaches, such as intermolecular Grubb's olefin metathesis, Heck and, Suzuki reactions were incorporated to functionalize the core structures of X and Y making it suitable for the preparation of a library of compounds.

Schiff bases of isatin: Inhibitory potential towards acetylcholinesterase and butyrylcholinesterase

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

A convenient synthesis of ortho-ortho disubstituted biphenyls containing an eight-membered lactam ring using radical chemistry

Compound 4 prepared from Isatin in two steps underwent an unusual radical-induced rearrangement reaction to yield 9 as the major product and 10 as the minor component. Compound 9 shows structural similarities to the antimitotic agent rhazinilam and the ga