59007-52-2

Basic information

• Product Name: 2-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-isoindole-1,3(2H)-dione
• CAS NO: 59007-52-2
• Molecular Formula: C₁₂H₇N₃O₄
• Molecular Weight: 257.2017
• Mol File: 59007-52-2.mol
• Article Data: 3

Chemical Properties

• Density: 1.617g/cm³
• Refractive Index: 1.688
• CAS DataBase Reference: 2-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-isoindole-1,3(2H)-dione(59007-52-2)
• EPA Substance Registry System: 2-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-isoindole-1,3(2H)-dione(59007-52-2)

Safety Data

• Hazardous Substances Data: 59007-52-2(Hazardous Substances Data)

Usage

Derivation

Synthetic derivative of glutamic acid

Initial Purpose

Sedative and antiemetic

Withdrawal from Market

Due to teratogenic effects causing severe birth defects

Current Uses

Treatment of multiple myeloma and leprosy

Potential Uses

Treatment of HIV/AIDS, Crohn's disease, and certain types of cancer

Mechanism of Action

Inhibition of tumor necrosis factor-alpha and other pro-inflammatory cytokines; anti-angiogenic effects

Immunomodulatory and Anti-inflammatory Properties

Present

Upstream product

• 85-44-9 phthalic anhydride 
• 932-52-5 5-Aminouracil 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant articles and documents

Efficient synthesis of 2-substituted phthalimides from phthalic acids in one step

Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The phthalimide central fragment frequently appears in biologically active compounds, materials, catalysts, and fluorescent probes, and therefore the development of general, fast, and convenient synthetic methods to this scaffold under neutral, acidic, and basic conditions would be attractive. After an initial screening, the use of acetonitrile, acetic acid, or pyridine in combination with microwave heating proved most promising. Experimental design was applied to these conditions to optimize the time, temperature, and concentration. This strategy has successfully generated synthetic methods that have been used to synthesize a series of phthalimides from phthalic acids and various amines or anilines in excellent yields. The developed methods have proven to be general, fast, convenient, and economic, and thus are expected to have broad utility to efficiently construct novel compounds for future biological and chemical applications. Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The developed methods are fast, general, high-yielding, do not use additives, and are based on 1:1 molar ratios.

Phtalimido derivatives of pyrimidine and thiazole heterocyclics

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