21640-33-5

Basic information

• Product Name: 2-METHYL-ISOQUINOLINE-1,3,4-TRIONE
• Synonyms: 2-METHYL-ISOQUINOLINE-1,3,4-TRIONE;2-METHYLISOQUINOLINE-1,3,4(2H)-TRIONE
• CAS NO: 21640-33-5
• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.16748
• Mol File: 21640-33-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-METHYL-ISOQUINOLINE-1,3,4-TRIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-ISOQUINOLINE-1,3,4-TRIONE(21640-33-5)
• EPA Substance Registry System: 2-METHYL-ISOQUINOLINE-1,3,4-TRIONE(21640-33-5)

Safety Data

• Hazardous Substances Data: 21640-33-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 47, p. 857, 1969 DOI: 10.1139/v69-136

Upstream product

• 491-34-9 N-methyl-1,2,3,4-tetrahydroquinoline 
• 20458-78-0 2-methyl-2,3-dihydro-1H-isoquinolin-4-one; hydrochloride 
• 6772-65-2 2-methyl-3,4-dihydro-2H-isoquinolin-1-one 
• 84484-46-8 4-imino-2-methylisoquinoline-1,3(2H,4H)-dione 
• 67-56-1 methanol 
• 4494-53-5 2-methyl-1,3(2H,4H)-isoquinolinedione 
• 79841-13-7 2-methyl-2,3-dihydroisoquinolin-4(1H)-one 
• 7664-93-9 sulfuric acid 
• 521-73-3 isoquinoline-1,3,4-trione 
• 74-88-4 methyl iodide 
• 703-59-3 homophthalic anhydride 
• 4594-71-2 N-methylisocarbostyril 
• 3947-77-1 2-methylisoquinolinium iodide 
• 7460-55-1 2-(2-bromoacetyl)benzoic acid methyl ester 

Downstream Products

• 550-44-7 N-methylphthalimide 
• 159029-75-1 ethyl 2,3-dihydro-1-hydroxy-2-methyl-3-oxo-1H-isoindole-1-carboxylate 
• 82820-46-0 C₂₄H₁₉N₃O₅ 
• 1221793-81-2 5-methyl-7-picolinoyl-5,6-dihydro-4H-dibenz[de,g]isoquinoline-4,6-dione 
• 1221793-80-1 7-benzoyl-5-methyl-4H-isoquinolino[5,4-fg]quinoline-4,6(5H)-dione 
• 1221793-83-4 7-benzoyl-5-methyl-4H-benzo[de]pyrido[4,3-g]isoquinoline-4,6(5H)-dione 
• 1221793-82-3 7-benzoyl-5-methyl-4H-isoquinolino[4,5-gh]quinoline-4,6(5H)-dione 
• 1221793-85-6 5-methyl-7-nicotinoyl-5,6-dihydro-4H-dibenz[de,g]isoquinoline-4,6(5H)-dione 
• 1221793-93-6 5-methyl-7-(pyrazine-2-carbonyl)-5,6-dihydro-4H-dibenz[de,g]isoquinoline-4,6(5H)-dione 
• 1221793-91-4 7-benzoyl-5-methyl-4H-isoquinolino[5,4-fg]quinoxaline-4,6(5H)-dione 
• 1221793-97-0 5-methyl-7-(quinoline-3-carbonyl)-5,6-dihydro-4H-dibenz[de,g]isoquinoline-4,6(5H)-dione 
• 1221793-95-8 7-benzoyl-5-methyl-4H-isoquinolino[4,5-jk]phenanthridine-4,6(5H)-dione 
• 1221793-89-0 5-methyl-7-(pyrimidine-5-carbonyl)-5,6-dihydro-4H-dibenz[de,g]isoquinoline-4,6(5H)-dione 
• 1221793-87-8 7-benzoyl-5-methyl-4H-isoquinolino[4,5-gh]quinazoline-4,6(5H)-dione 

Relevant articles and documents

Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones

Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to

Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors

A series of isoquinoline-1,3,4-trione derivatives were identified as novel and potent inhibitors of caspase-3 through structural modification of the original compound from high-throughput screening. Various analogues (2, 6, 9, 13, and 14) were synthesized and identified as caspase inhibitors, and the introduction of a 6-N-acyl group (compound 13) greatly improved their activity. Some of them showed low nanomolar potency against caspase-3 in vitro (for example, for 6k, IG50 = 40 nM) and significant protection against apoptosis in a model cell system. Additionally, compound 13f demonstrated a dose-dependent decrease in infarct volume in the transient MCA occlusion stroke model. The present small-molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.

ISOQUINOLINE -1,3,4-TRIONE, THE SYNTHETIC METHOD AND THE USE THEREOF

The invention relates to various substituted isoquinoline-1,3,4-trione, the synthetic method thereof and the use for treating neurodegenerative diseases, especially as the medicine for Alzhermer's disease, apoplexy and brain ischemic injuries. The compound is represented by the following structure formula: Wherein substituents R1 can be one, two or three groups optionally selected from the group consisting of H; alkyl; hydroxyl; alkyl substituted by the groups including halogen, alkoxyl or hydroxyl; alkoxyl or alkylamino substituted by the groups including halogen, alkoxyl or hydroxyl; C2-C6 alkenyl substituted by oxygen or amine; C3-C6 cycloalkyl; substituted aryl; benzyl; alkanoyl; alkanoyl substituted by the groups including halogen, alkoxyl or hydroxyl; C2-C6 enoyl; C3-C6 cycloalkanoyl; tert-butoxycarbonyl; benzoyl; benzoyl substituted by one, two or three groups including alkylamino; benzylacyl; benzylacyl substituted by one, two or three groups including alkylamino; thienoyl; adamantylcarbonyl; mandeloyl; alkoxyl; alkylamino; cycloalkoxyl; cycloalkylamino; amino; acylamino; alkyloxycarbonyl; cycloalkoxycarbonyl; alkanoylxy; alkanoylamino; cycloalkyanoylxy; cycloalkanoylamino; ureido; urenylene; alkanoyl; nitro; carboxyl; R2 is H; alkyl; alkyl or C1-C4 cycloalkyl substituted by the groups including halogen, alkoxyl or hydroxyl; C2-C6 alkenyl; aryl; substituted aryl; X is H, CH2, NH, O, or S; Y is CH, or N.

On the reactions of 1,3-isoquinolinediones with singlet oxygen

Reactions of 1,3-isoquinolinediones 5 and 4-alkylated 1,3- isoquinolinediones 13 with singlet oxygen are entirely dominated by their enolization and proceed smoothly in benzene in the presence of pyridine as a base and a hydrogen bond acceptor. The products are triketones 6 and benzoisofuranones 7 for 5, and hydroperoxides 14, hydroxides 15 and benzoisofuranones 16 for 13. It was found that hydrolysis of 6 afforded the isoindolones 8 and not products 7, whereas alkaline cleavage of the hydroperoxide 14a yielded not only 16a, but also the isoindolone 19a, In view of these observations, an unusual [4+2] cycloaddition of the electron-rich enol 21 with singlet oxygen is proposed to be responsible for the formation of products 7 and 16, while products 6, 14 and 15 arise from both the [4+2] cycloaddition and the usual Schenck ene reaction pathways. This special diene reactivity of the isoquinolinone system towards singlet oxygen is further interpreted by frontier molecular orbital (FMO) interaction considerations.

Dye-sensitized photooxygenations of 1,3-isoquinolinediones

Singlet oxygen reactions of 1,3-isoquinolinediones 1a-1e could be sensitized by the anionic sensitizer Rose Bengal (RB) in methanol or by tetraphenylporphin (TPP) in the presence of pyridine as a base and a consolvent in benzene. The products are the corr

Mechanism of the chemiluminescence of biisoquinolinium salts

1,1′-Biisoquinolinium salts (BIQ2+2X-) are known to exhibit chemiluminescence on addition of hydrogen peroxide in an alkaline solution. Reduction of BIQ2+ with Na2S 2O4-Na2CO3 or Na-Hg gave the radical cation BIQ+? and then the neutral two-electron reduced species, 1,1′-biisoquinolylidene (BIQ), which was characterised by mass spectrometry, UV-VIS and 1H NMR spectroscopy. This electron-rich olefin instantaneously reacted with molecular oxygen showing a blue luminescence in organic solvents. Treatment of BIQ2+ or BIQ+? with KO2 in dimethyl sulfoxide (DMSO) or acetonitrile also caused light emission. The chemiluminescence spectra of both BIQ-3O 2 and BIQ2+-KO2 reactions were the same as that of BIQ2+-H2O2-OH- and the main product was an isoquinolinone derivative in either case. In the case of 2,2′-ethylene-bridged BIQ2+, the chemiluminescence spectrum coincided with the fluorescence spectrum of the corresponding biisoquinolinone. A plausible reaction pathway for the chemiluminescence of the BIQ 2+-H2O2-OH- system is as follows: BIQ2+ is reduced by electron donors such as OH- and OOH- to BIQ, which reacted with molecular oxygen to give a 1,2-dioxetane. Thermal decomposition of this intermediate generates the excited state of isoquinolinone. The 'photoproducts' from isoquinolinones were obtained in the chemiluminescence reaction as minor products, confirming the chemical formation of the excited state of the isoquinolinones.

1,3,4(2H)-Isoquinolinetrione Herbicides: Novel Redox Mediators of Photosystem I

A series of 1,3,4(2H)-isoquinolinetriones have found to be fast-acting post-emergence herbicides, producing symptoms of desiccation. These redox-active compounds are very potent stimulators of the light-dependent consumption of oxygen at photosystem I in