50-46-4

Basic information

• Product Name: 5,8-Dihydroisoquinoline-5,8-dione
• Synonyms: 5,8-Dihydroisoquinoline-5,8-dione;5,8-Isoquinolinedione;Nsc76882;isoquinoline-5,8-dione
• CAS NO: 50-46-4
• Molecular Formula: C₉H₅NO₂
• Molecular Weight: 159.1415
• Mol File: 50-46-4.mol

Chemical Properties

• Boiling Point: 333.6°Cat760mmHg
• Flash Point: 159.9°C
• Appearance: /
• Density: 1.374g/cm³
• Vapor Pressure: 0.000135mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 5,8-Dihydroisoquinoline-5,8-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-Dihydroisoquinoline-5,8-dione(50-46-4)
• EPA Substance Registry System: 5,8-Dihydroisoquinoline-5,8-dione(50-46-4)

Safety Data

• Hazardous Substances Data: 50-46-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5,8-Dihydroisoquinoline-5,8-dione is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical structure allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Organic Electronic Devices:
5,8-Dihydroisoquinoline-5,8-dione has been studied for its potential applications in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells. Its electronic properties make it a promising candidate for improving the performance and efficiency of these devices.
Used as a Synthetic Precursor:
5,8-Dihydroisoquinoline-5,8-dione serves as a synthetic precursor for the production of various organic compounds. Its versatile chemical structure enables the synthesis of a wide range of molecules with diverse applications in different industries.

InChI:InChI=1/C9H5NO2/c11-8-1-2-9(12)7-5-10-4-3-6(7)8/h1-5H

Upstream product

• 55087-23-5 5,8-dimethoxyisoquinoline 
• 119-65-3 isoquinoline 
• 607-32-9 5-nitroisoquinoline 
• 54879-54-8 5,8-dimethoxy-3-methyl-2-tosyl-1,2-dihydroisoquinoline 
• 54879-36-6 N-(2,5-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide 
• 1432611-60-3 N-(2,5-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzenesulfonamide 
• 54879-79-7 acetaldehyde dimethyl acetal 
• 54879-66-2 acetaldehyde dimethyl acetal 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 1125-60-6 isoquinolin-5-ylamine 
• 156901-61-0 8-amino-5-nitro-isoquinoline 
• 2439-04-5 5-hydroxyisoquinoline 
• 1127-49-7 5,8-diaminoisoquinoline 

Downstream Products

• 46492-08-4 benz[g]isoquinoline-5,10-dione 
• 118680-81-2 7-aminoisoquinoline-5,8-dione 

Relevant articles and documents

Synthesis and biological evaluation of caulibugulones A-E

The marine bryozoan metabolites caulibugulone A-E were prepared from a readily available isoquinoline dione. These natural products were found to be potent and selective inhibitors of the dual specificity phosphatase Cdc25B.

Total synthesis of the marine alkaloids Caulibugulones A and D

Total synthesis of the marine cytotoxic alkaloids Caulibugulones A and D is accomplished in three steps with an overall yield of 60-62% from easily accessible starting materials. The key features include isoquinoline-5,8-diol core construction by ammonia mediated iminoannulation of 2-ethynyl-3,6-dihydroxybenzaldehyde, and subsequent in situ oxidation followed by oxidative amination.

Ezrin inhibitors and methods of making and using

The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growth of a cancer cell.

Design, synthesis and biological evaluation of ezrin inhibitors targeting metastatic osteosarcoma

Respiratory failure due to pulmonary metastasis is the major cause of death for patients with osteosarcoma. However, the molecular basis for metastasis of osteosarcoma is poorly understood. Recently, ezrin, a member of the ERM family of proteins, has been associated with osteosarcoma metastasis to the lungs. The small molecule NSC 668394 was identified to bind to ezrin, inhibit in vitro and in vivo cell migration, invasion, and metastatic colony survival. Reported herein are the design and synthesis of analogues of NSC 668394, and subsequent functional ezrin inhibition studies. The binding affinity was characterized by surface plasmon resonance technique. Cell migration and invasion activity was determined by electrical cell impedance methodology. Optimization of a series of heterocyclic-dione analogues led to the discovery of compounds 21k and 21m as potential novel antimetastatic agents.

Exploitation of a tuned oxidation with N -haloimides in the synthesis of caulibugulones A-D

Marine alkaloids caulibugulones A-D were synthesized in six steps starting from the readily available 2,5-dimethoxybenzaldehyde. Pomeranz-Fritsch reaction of N-(2,5-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzenesulfonamide proceeded smoothly to gi

μ-oxo-bridged hypervalent iodine(III) compound as an extreme oxidant for aqueous oxidations

We have found that in aqueous oxidations the -oxo-bridged hypervalent iodine trifluoroacetate reagent 1 {[(PhI(OCOCF]} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. -Oxo-bridged 1 in aqueous media thus provided dearomatized quinones 3 in excellent yields in most cases compared to conventional phenyliodine(III) diacetate and bis(trifluoroacetate), as a result of the rapid oxidation of both phenols and naphthols 2. Furthermore, the oxidation reactions proceeded even in water using water-soluble -oxo oxidant 1, which has promise for -oxo-bridged reagent 1 to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate). Georg Thieme Verlag Stuttgart New York.

Synthesis and biological evaluation of new cytotoxic azanaphthoquinone pyrrolo-annelated derivatives

A series of azanaphthoquinone pyrrolo-annelated derivatives attached to basic side chains have been synthesized. The antiproliferative activities of all compounds were evaluated on at least four different cell lines. The effects on cell cycle and intercalation were investigated.

Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone

Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity. CSIRO 2008.

Synthesis and biological evaluation of novel cytotoxic azanaphthoquinone annelated pyrrolo oximes

Two series of azanaphthoquinone annelated pyrrolo oximes have been synthesized. The antiproliferative activities of 10 compounds were evaluated on at least four different cell lines. One series of pyrrolo derivatives showed high cytotoxic activity. The effects on cell cycle and caspase activity were investigated. Compounds 9a and 9b showed an accumulation of cells in G2/M phase. Substantial and dose-dependent caspase activity was found after treatment of cells with 9a and 9b. This indicates an apoptosis inducing property of these compounds.

7-(Substituted-phenyl)amino-5,8-isoquinolinediones: Synthesis and cytotoxic activities on cancer cell lines

6-Chloro-7-(substituted-phenyl)amino-5,8-isoquinolinediones (3a-3u) and 7-(substituted-phenyl)amino-5,8-isoquinolinediones (4a-4d) were synthesized by nucleophilic substitution of 6,7-dichloro-5,8-isoquinolinedione (8) and 5,8-isoquinolinedione (9) with appropriate arylamines. The quinones 3a-3u and 4a-4d were evaluated for in vitro cytotoxic activities against five solid tumor cell lines such as A549, SK-OV-3, SK-MEL-2, XF498 and HCT-15. Among them, 3c, 3d, 3f and 3h exhibited potent activities against the cell lines HCT-15 and SK-MEL-2.