4770-30-3

Basic information

• Product Name: 2-(dimethylamino)-1H-isoindole-1,3(2H)-dione
• Synonyms: 2-(dimethylamino)isoindoline-1,3-dione
• CAS NO: 4770-30-3
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.1986
• Mol File: 4770-30-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 311.9°C at 760 mmHg
• Flash Point: 139.6°C
• Density: 1.32g/cm³
• Vapor Pressure: 0.000548mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: 2-(dimethylamino)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(dimethylamino)-1H-isoindole-1,3(2H)-dione(4770-30-3)
• EPA Substance Registry System: 2-(dimethylamino)-1H-isoindole-1,3(2H)-dione(4770-30-3)

Safety Data

• Hazardous Substances Data: 4770-30-3(Hazardous Substances Data)

Usage

General Description

2-(dimethylamino)-1H-isoindole-1,3(2H)-dione, also known as thalidomide, is a pharmaceutical drug and a synthetic derivative of glutamic acid. It was originally developed as a sedative and an antiemetic, but was later withdrawn from the market due to its severe teratogenic effects, causing birth defects in babies when taken by pregnant women. Despite its controversial history, thalidomide has found new uses in modern medicine, particularly as a treatment for leprosy and certain types of cancer. It works by inhibiting the production of tumor necrosis factor-alpha and other inflammatory cytokines, as well as by disrupting the formation of new blood vessels that feed tumors. Thalidomide is also being studied for potential applications in various autoimmune and inflammatory diseases.

Upstream product

• 85-44-9 phthalic anhydride 
• 57-14-7 N,N-Dimethylhydrazine 
• 55484-54-3 N,N-dimethylhydrazine dihydrochloride 

Downstream Products

• 28352-78-5 2-(Dimethylamino)-3-hydroxy-3-phenyl-2,3-dihydroisoindol-1-one 
• 149549-11-1 4-(4-methylthiophen-2-yl)-phthalazin-1(2H)-one 
• 945595-80-2 AMG 900 
• 1372642-13-1 3-benzyl-2-(dimethylamino)-3-hydroxyisoindolin-1-one 
• 1372642-15-3 3-cyclohexyl-2-(dimethylamino)-3-hydroxyisoindolin-1-one 
• 1372642-16-4 2-(dimethylamino)-3-hydroxy-3-(phenylethynyl)isoindolin-1-one 
• 1372642-18-6 2-(dimethylamino)-3-hydroxy-3-((3-hydroxyphenyl)ethynyl)isoindolin-1-one 
• 1372642-11-9 3-(4-chloro-3-methoxyphenyl)-2-(dimethylamino)-3-hydroxyisoindolin-1-one 
• 1372642-49-3 2-(dimethylamino)-4-phenyl-3,4-dihydro-1H-benzo[c]azepine-1,5(2H)-dione 
• 1372642-09-5 2-(dimethylamino)-3-hydroxy-3-m-tolylisoindolin-1-one 

Relevant articles and documents

CRYSTALLINE FORMS OF N-(4-((3-(2-AMINO-4-PYRIMIDINYL) - 2-PYRIDINYL)OXY)PHENYL)-4-(4-METHYL-2-THIENYL)-1 -PHTHALAZINAMINE PHARMACEUTICALLY ACCEPTABLE SALTS AND USES THEREOF

The present invention relates to crystalline forms and co-crystal forms of pharmaceutically acceptable salts of the compound, N-(4-((3-(2-amino-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)-4-(4-methyl-2-thienyl)-1-phthalazinamine (AMG 900, and pharmaceutical compositions comprising said crystalline and co-crystal forms thereof. The invention further provides uses of the crystalline foms and compositions, to treat cancer, including various types of solid tumors and hematologic cancer including myeloma and leukemia.

Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3-hydroxyisoindolin-1-ones

Figure Persented: Herein we describe a general three-step synthesis of 4-substituted chlorophthalazines in good overall yields. In the key step, N,N-dimethylaminophthalimide (8a) directs the selective monoaddition of alkyl, aryl, and heteroaryl organometallic reagents to afford 3-substituted 3-hydroxyisoindolinones 9b, 9i-9am. Many of these hydroxyisoindolinones are converted to chlorophthalazines 1b-1v via reaction with hydrazine, followed by chlorination with POCl3. We have also discovered two novel transformations of 3-vinyl- and 3-alkynyl-3-hydroxyisoindolinones. Addition of vinyl organometallic reagents to N,N-dimethylaminophthalimide (8a) provided dihydrobenzoazepinediones 15a-15c via the proposed ring expansion of 3-vinyl-3-hydroxyisoindolinone intermediates. 3-Alkynyl-3-hydroxyisoindolinones react with hydrazine and substituted hydrazines to afford 2-pyrazolyl benzoic acids 16a-16d and 2-pyrazolyl benzohydrazides 17a-17g rather than the expected alkynyl phthalazinones.

AURORA KINASE MODULATORS AND METHOD OF USE

The present invention relates to chemical compounds having a general formula (I) wherein A1-5 and 7-8, D', L1, L2, R1, R3, R6-8, n and o are defined herein, and synthetic intermediates, which are capable of modulating the activity of Aurora kinase proteins and, thereby, influencing various disease states and conditions related to the activities of Aurora kinases. For example, the compounds are capable of influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of Aurora kinase.