3484-32-0

Basic information

• Product Name: 1-METHYL-5-NITRO-ISATIN
• Synonyms: 1-METHYL-5-NITRO-ISATIN;1-METHYL-5-NITROINDOLINE-2,3-DIONE
• CAS NO: 3484-32-0
• Molecular Formula: C₉H₆N₂O₄
• Molecular Weight: 206.15
• Product Categories: pharmacetical
• Mol File: 3484-32-0.mol

Chemical Properties

• Boiling Point: 391.9°C at 760 mmHg
• Flash Point: 190.8°C
• Appearance: /
• Density: 1.533g/cm³
• Vapor Pressure: 2.38E-06mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-METHYL-5-NITRO-ISATIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-5-NITRO-ISATIN(3484-32-0)
• EPA Substance Registry System: 1-METHYL-5-NITRO-ISATIN(3484-32-0)

Safety Data

• Hazardous Substances Data: 3484-32-0(Hazardous Substances Data)

Usage

Preparation

A mixture of nitroisatin 31 (10 g, 0.052 mol), MeI (16.21 ml, 0.260 ?mol) and K2CO3 (21.56 g, 1.56 mol) in anhydrous DMF was stirred ?overnight at room temperature. Water was added to the reaction ?mixture and acidified with dilute HCl till acidic to pH paper. A ?yellow solid separated, 1-Methyl-5-nitroisatin was filtered and washed thoroughly ?with water till neutral to pH paper and air dried to a constant weight (9.66 g).

Synthesis Reference(s)

Journal of Medicinal Chemistry, 39, p. 5072, 1996 DOI: 10.1021/jm960603e

InChI:InChI=1/C9H6N2O4/c1-10-7-3-2-5(11(14)15)4-6(7)8(12)9(10)13/h2-4H,1H3

Upstream product

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 611-09-6 5-nitroisatin 
• 74-88-4 methyl iodide 
• 5279-61-8 N-methyl-4-(4-nitrophenyl)formamide 
• 29906-67-0 1-methyl-5-nitro-1H-indole 
• 91-56-5 indole-2,3-dione 
• 20870-89-7 1-methyl-5-nitro-1,3-dihydro-indol-2-one 
• 77-78-1 dimethyl sulfate 
• 74-87-3 methylene chloride 

Downstream Products

• 1219433-01-8 10'-amino-1,2-dihydro-1-methyl-5-nitro-2,7'-dioxospiro[3H-indole-3,8'(7H,8H)-phenaleno[1,2-b]pyran]-9'-carbonitrile 
• 1217109-99-3 5'-(2-hydroxybenzoyl)-1-methyl-5-nitro-1',3'-diphenyl-5',7'-dihydrospiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2,6'(1'H)-dione 
• 1379768-26-9 C₂₇H₃₁N₃O₉ 
• 1385027-11-1 1-methyl-5-nitro-3'-phenylspiro[3H-indole-3,2'-[4H]-pyrido-[3,2-e]-1,3-thiazine]-2,4'(1H)-dione 
• 1441224-39-0 3-(tert-butylcarbamoyl)-1-methyl-5-nitro-2-oxoindolin-3-yl benzoate 
• 1394843-51-6 3-hydroxy-1-methyl-6-nitroquinolin-2(1H)-one 
• 1527504-76-2 1-methyl-5-nitro-3'-(phenylamino)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione 
• 2216750-84-2 2-((6-amino-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)oxy)-N-methylacetamide 

Relevant articles and documents

Activation of the NC-H bond of Baylis-Hillman adducts of N-methylisatin with CAN/ROH

A facile method for activation of the NC-H bond of N-methylisatin and Baylis-Hillman adducts of N-methylisatin with cerium ammonium nitrate (CAN) and saturated and unsaturated alcohols is reported. Adducts bearing an ester group at the activated alkene afford functionalized ethers, while those with a nitrile afforded ethers and nitrated aromatic products in good yield.

Synthesis and in vitro cytotoxicity evaluation of isatin-pyrrole derivatives against HepG2 cell line

This paper reports the synthesis and in vitro cytotoxicity evaluation of isatin-pyrrole derivatives 5-8, obtained from the appropriate isatins with pyrrole, with good yields and purity. The product structures were confirmed through spectroscopy methods. Furthermore, the MTT assay on the human liver cancer HepG2 cell lines revealed moderate activity in all compounds, which was highest in sample 6 (IC50 0.47 μM). The anticancer activity was affiliated with the presence of a nitro group at C-5 and N-methyl of the isatin scaffold.

Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents

3H-Spiro[1,3-benzothiazole-2,3′-indol]-2′(1′H)-ones 3a-c and 4a-e were synthesized from treating the 5-substituted 1H-indole-2,3-diones with 2-aminothiophenol in ethanol. The structures were confirmed by elemental analyses, spectrometry (IR, 1H NMR, 13C NMR, HSQC-2D and LCMS-APCI) and single crystal X-ray analysis. The new compounds were screened for their antioxidant activities such as the Fe3+/ascorbate system induced inhibition of lipid peroxidation (LP) in liposomes, trolox equivalent antioxidant capacity (TEAC), scavenging effect on diphenylpicryl hydrazine (DPPH{radical dot}), and reducing power. These compounds showed potent scavenging activities against DPPH{radical dot} and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS{radical dot}+) radicals, reducing powers, and strong inhibitory capacity on lipid peroxidation. Compound 4a incorporating methyl both at R1 and R2 was found to be the most potent antioxidant described in this study. Compounds 3b and 4b were selected as representative compounds by the National Cancer Institute for screening against anticancer activity and these compounds were found to be cytotoxic against CNS cancer cell line SNB-75 in the primary screen.

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

BIFUNCTIONAL MOLECULES CONTAINING AN E3 UBIQUITINE LIGASE BINDING MOIETY LINKED TO A BCL6 TARGETING MOIETY

Bifunctional compounds, which find utility as modulators of B-cell lymphoma 6 protein (BCL6; target protein), are described herein. In particular, the bifunctional compounds of the present disclosure contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand that binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The bifunctional compounds of the present disclosure exhibit a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

Novel isatin derivative nitration method

The invention belongs to the technical field of chemical pharmacy and fine chemical engineering preparation, and particularly discloses a novel isatin derivative nitration method. Trifluoroacetic acidis adopted to replace traditional sulfuric acid, so tha

BCL6-targeting aromatic ring five-membered aromatic heterocyclic micromolecular organic compound and derivative and application thereof

The invention discloses an aromatic ring five-membered aromatic heterocyclic micromolecular organic compound or related analogues or pharmaceutically acceptable salts thereof. The structures of the compound are shown as formulas (I-IX). The invention also

Synthesis, characterization and anticancer activity of (5,1-substituted)-3-(indoline-4-(thiophene- 2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1h-imidazole-5-one derivatives

The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives (4a-j) to yield final compounds 5a-j. The organic potentials of the newly synthesized imidazole-5-one derivatives have been evaluated for their in vitro anticancer activity by MTT assay method. It against MCF-7 cells as comparison with doxorubicin popular drug. The synthesized compounds 5e, 5f and 5j exhibited excellent anticancer activity against MCF-7 cell lines.

Synthesis, anti-proliferative activity, theoretical and 1H NMR experimental studies of Morita–Baylis–Hillman adducts from isatin derivatives

Abstract: Quaternary or spirocyclic 3-substituted-3-hydroxy-2-oxindole is considered a privileged scaffold. In other words, it is a molecular core present on several compounds with a wide spectrum of biological activities. Among its precursors, activated ketones (isatin nucleus) can be used as interesting starting points to Morita–Baylis–Hillman adducts derivatives, a class of compounds with good cytotoxic potential. In this paper, we present the synthesis, anti-proliferative activity against lung cancer cell line and a theoretical conformational study of 21 of Morita–Baylis–Hillman adducts from isatin derivatives, by DFT quantum chemical calculations, followed by a SAR and QSAR analysis. Besides, an efficient synthetic protocol and good biological activity profile were highlighted interesting observations about 1H NMR experimental spectra, molecular modeling results and crystallographic data available. Graphical abstract: [Figure not available: see fulltext.]

Synthesis and anticancer activity evaluation of azepinobisindoles;the isomeric iheyamine A-derivatives

Azepinobisindole derivatives, the isomeric Iheyamine skeleton, were prepared and their anticancer activity evaluation were investigated against two human cancer cell lines, Hepatocellular carcinoma (HepG2) and human cervical cancer line (HeLa) as well as the normal cell line (Vero cell line) using MTT assay. The anticancer activity results indicated that 2-methoxy-5-methyl-5H-azepino[2,3-b:4,5-b]diindole was the most active derivative against tested cell lines. Additionally, molecular docking study in silico the possible inhibitory effect of cyclin-dependent kinase 2 (CDK2) by the azepinoindole revealed that all synthesized compounds fit well in the binding cavity of CDK2.