2058-74-4

Basic information

• Product Name: N-METHYLISATIN
• Synonyms: 1-methyl-1h-indole-3-dione;1-methyl-indole-2,3-dione;1-methyl-indole-3-dione;AKOS BBS-00000999;AKOS BC-1698;1-METHYL-1H-INDOLE-2,3-DIONE;1 METHYLISATINE;1-METHYLISATIN
• CAS NO: 2058-74-4
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: 218-164-9
• Product Categories: pharmacetical;Building Blocks;Heterocyclic Building Blocks;Indoles;Heterocycles
• Mol File: 2058-74-4.mol
• Article Data: 277

Chemical Properties

• Melting Point: 130-133 °C(lit.)
• Boiling Point: 287.44°C (rough estimate)
• Flash Point: 137.4 °C
• Appearance: Orange to brownish/Crystalline Powder
• Density: 1.314
• Vapor Pressure: 0.00164mmHg at 25°C
• Refractive Index: 1.5050 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -2.41±0.20(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 128280
• CAS DataBase Reference: N-METHYLISATIN(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLISATIN(2058-74-4)
• EPA Substance Registry System: N-METHYLISATIN(2058-74-4)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NL7939000
• HazardClass: IRRITANT
• Hazardous Substances Data: 2058-74-4(Hazardous Substances Data)

Usage

Chemical Properties

ORANGE TO BROWNISH CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 2058-74-4 differently. You can refer to the following data:
1. 1-Methylisatin is used as a reactant for stereoselective preparation of spirobicyclic and bis-spirotricyclic pyrazolidinones, for regioselective preparation of spirocyclic oxindole-butenolides, for synthesis of spiro-oxindoles, for preparation of unsymmetrical oxindoles, for stereoselective preparation of hydroxyloxindoles via Morita-Baylis-Hillman reaction, for preparation of pyridinecarboxylic acid [(oxo)indolylidene)hydrazide derivatives (Schiff base hydrazides) as antibacterial agents.
2. Reactant for stereoselective preparation of spirobicyclic and bis-spirotricyclic pyrazolidinonesReactant for regioselective preparation of spirocyclic oxindole-butenolidesReactant for synthesis of spiro-oxindolesReactant for preparation of unsymmetrical oxindolesReactant for stereoselective preparation of hydroxyloxindoles via Morita-Baylis-Hillman reactionReactant for preparation of pyridinecarboxylic acid [(oxo)indolylidene)hydrazide derivatives (Schiff base hydrazides) as antibacterial agents

Synthesis Reference(s)

Journal of Medicinal Chemistry, 47, p. 2089, 2004 DOI: 10.1021/jm030483s

General Description

The interaction between 1-methylisatin and human adult haemoglobin was studied using the circular dichroism (CD) spectroscopic, anisotropy and FTIR investigations.

InChI:InChI=1/C9H7NO2/c1-10-7-5-3-2-4-6(7)8(11)9(10)12/h2-5H,1H3

Upstream product

• 3335-86-2 3-hydroxy-1-methyl-indolin-2-one 
• 64-17-5 ethanol 
• 61-70-1 N-methyl-2-indolinone 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 16526-19-5 (E)-1,4-dibromo-2-methylbut-2-ene 
• 40800-68-8 1-methyl-3-(methylthio)indolin-2-one 
• 38072-57-0 (Z)-2-benzylidene-1-methylindolin-3-one 
• 76325-64-9 3-hydroxy-1-methyl-3-(2'-oxopropyl)indolin-2-one 
• 113737-84-1 3-hydroxy-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 603-76-9 1-methylindole 
• 180623-97-6 2,3-diiodo-1-methyl-1H-indole 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 74-83-9 methyl bromide 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 109653-31-8 1-methyl-3-(1-methyl-2-oxo-5-phenyl-1,2-dihydro-pyrrol-3-ylidene)-indolin-2-one 
• 81235-51-0 1-methyl-2,2-diphenyl-indolin-3-one 
• 22136-54-5 N-methyl-1,3-dihydro-3,3-diphenyl-2H-indol-2-one 
• 62542-44-3 1-methyl-2-quinoline-4-carboxylic acid 
• 109813-89-0 1-methyl-3-(2-oxo-5-phenyl-1,2-dihydro-pyrrol-3-ylidene)-indolin-2-one 
• 15096-16-9 N-Methylisatin 3-phenylhydrazone 
• 15757-32-1 3-hydroxy-1-methyl-3-phenyl-1,3-dihydro-2H-indol-2-one 
• 75-07-0 acetaldehyde 
• 60463-77-6 1-methyl-3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one 
• 65880-39-9 1-N-methyl-indolo <2,3-b> quinoxaline 
• 108124-50-1 1-methyl-3-(2-oxo-5-phenyl-furan-3-ylidene)-indolin-2-one 
• 3265-24-5 (E)-3-(hydroxyimino)-1-methylindolin-2-one 
• 3484-32-0 1-methyl-5-nitro-1H-indole-2,3-dione 
• 119-68-6 N-Methylanthranilic acid 

Relevant articles and documents

Synthesis of novel 5-substituted indirubins as protein kinases inhibitors

In an effort to identify new pharmacological inhibitors of disease-relevant protein kinases with increased potency and selectivity, we synthesized and evaluated new 5-substituted indirubins. The effects of 34 indirubin derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3, as well as on SH-SY5Y human neuroblastoma cell survival, were investigated.

AcOH-mediated dichloroimination of indoles using chloramine-B: A facile access to 2,3-functionalized indolines

A new and mild method for the efficient synthesis of 3,3-dichloro-2-sulfonyliminoindolines via AcOH-mediated dichloroimination of indoles using chloramine-B is presented. Application of this method to the efficient construction of pyrrolidinoindoles and N-C3 linked pyrrolidinoindolines is demonstrated.

C-H Activation Relay (CHAR): An Efficient Construction of Isatin Skeleton by Aerobic Oxidation of Glycine Esters

Directed by the strategy of C-H activation relay (CHAR), an efficient construction of isatin skeleton was developed through catalytic oxidation of glycine esters. The mechanistic study reveals that the oxidation of the relatively active C-H bonds initiated the followed activation of remote and inert C-H bonds, and an intramolecular 1,6-hydrogen shift was involved as a key step.

New and efficient one-pot synthesis of functionalized γ-spirolactones mediated by vinyltriphenylphosphonium salts

The addition of dimethyl acetylenedicarboxylate to isatin derivatives in the presence of triphenylphosphine leading to new highly functionalized γ-spirolactones is reported.

First X-ray structural characterization of isatin Schiff base derivative. NMR and theoretical conformational studies

Isatin (1H-indole-2,3-dione) is an endogenous natural compound under intense development in medicinal chemistry. Here, we characterize isatin Schiff base derivative by X-ray crystallography. We describe a derivative that crystallizes E-isomer form in the triclinic space group P 1ˉ; a = 5.9580 (4) A?, b = 8.4184 (7) A?, c = 14.1801 (14) A?, α = 73.962 (8)°, β = 83.184 (7)°, γ = 81.143 (6)°. NMR data show that E-conformer interconverts to the Z-conformer when dissolved, this equilibrium weakly depends on the solvent type. The Z-isomer geometry and the energetics of ΔEE-Zinterconversion barriers were determined by quantum chemical calculations. The isomers are further characterized by means of FT-IR and UV-Vis spectroscopy.

[3 + 3] Formal Cycloadditions of Nitrones from Isatins and Azaoxyallyl Cations for Construction of Spirooxindoles

A [3 + 3] formal cycloaddition reaction between in situ formed azaoxyallyl cations and nitrones from isatins has been developed, furnishing a spectrum of spiro[1,2,4-oxadiazinan-5-one]oxindoles in good to excellent yields with excellent diastereoselectivity. This method provides direct and efficient access to potentially bioactive spirooxindoles incorporating a six-membered heterocyclic scaffold.

Synthesis and biological evaluation of new [1,2,4]triazino[5,6-b]indol-3-ylthio-1,3,5-triazines and [1,2,4]triazino[5,6-b]indol-3-ylthio-pyrimidines against Leishmania donovani

A series of [1,2,4]triazino[5,6-b]indol-3-ylthio-1,3,5-triazines and [1,2,4]triazino[5,6-b]indol-3-ylthio-pyrimidines were synthesized and screened for their in vitro antileishmanial activity against Leishmania donovani. Among all, 8 compounds have shown more than 90% inhibition against promastigotes and IC50 in the range of 4.01-57.78 μM against amastigotes. Compound 5, a triazino[5,6-b]indol-3-ylthio-1,3,5-triazine derivative was found to be the most active and least toxic with 20- & 10-fold more selectivity (S.I. = 56.61) as compared to that of standard drugs pentamidine and sodium stibogluconate (SSG), respectively.

Construction of spiro[indoline]oxindoles through one-pot thermal-induced [3+2] cycloaddition/silica gel-promoted fragmentation sequence between isatin ketonitrones and electron-deficient alkynes

One-pot thermal-induced [3+2] cycloaddition/silica gel-promoted fragmentation sequence between isatin ketonitrones and electron-deficient alkynes affords spiro[indoline]oxindoles in moderate to excellent yields along with good diastereoselectivities. The

TBHP Mediated Substrate Controlled Oxidative Dearomatization of Indoles to C2/C3-Quaternary Indolinones

Oxidative dearomatization of indoles with 70 % aqueous tert-butylhydroperoxide (TBHP) in the absence of any metal salts/organic solvents gave the corresponding C2/C3-quaternary indolinones under open-air reaction conditions. The nature of substituent on the indole nitrogen dictates the type of product formed in these reactions. Free (NH)-indoles gave C2-quaternary indolinone derivatives whilst (NR)-indoles yielded C3-quaternary indolinones as the major product. Moreover, the addition of an excess amount of TBHP also facilitated the one-pot transformation of (NR)-indoles to the corresponding isatin derivatives.

Synthesis of novel functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis-Hillman adducts of iatin and heteroaldehydes with azomethine ylides via [3+2]-cycloaddition

A novel regioselective synthesis of a number of functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis-Hillman adducts of satin and heteroaldehydes via [3+2] cycloaddition of azomethine ylides in excellent yields has been reported.

The application of Morita-Baylis-Hillman reaction: Synthetic studies on perophoramidine

A new concise methodology was developed for the synthesis of the two vicinal quaternary centers of the natural product perophoramidine. Key steps involved the Morita–Baylis–Hillman reaction, reductive cyclization and allylic alkylation. Moreover, most con

Base-mediated allylation of N-2,2,2-trifluoroethylisatin ketimines and its application in aza-Prins reactions

The aza-Prins reaction of allylic imines triggered by N-2,2,2-trifluoroethylisatin ketimine is accomplished for the synthesis of spirooxindole derivatives involving trifluoromethyl group in the presence of TMSX. This cyclization reaction is operationally simple and proceeds under mild conditions using non-toxic reagents. Notably, while the previous our work could not be compatible with TMSX (X = Cl, I, etc) in one-pot process, this work describes successful aza-Prins reaction with TMSX (X = Cl, I, etc) via step-by-step process.

Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors

Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.