93272-45-8

Basic information

• Product Name: 2-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione
• CAS NO: 93272-45-8
• Molecular Formula: C₁₄H₁₂N₄O₅
• Molecular Weight: 316.2689
• Mol File: 93272-45-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 605.8°C at 760 mmHg
• Flash Point: 320.2°C
• Density: 1.61g/cm³
• Vapor Pressure: 1.58E-15mmHg at 25°C
• Refractive Index: 1.734
• CAS DataBase Reference: 2-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione(93272-45-8)
• EPA Substance Registry System: 2-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione(93272-45-8)

Safety Data

• Hazardous Substances Data: 93272-45-8(Hazardous Substances Data)

Usage

Molecular structure

2-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione is a complex organic compound consisting of various functional groups and rings.

Functional groups

The compound contains a hydroxy group (-OH), a nitro group (-NO2), an imidazole ring, and an isoindole ring.

Pharmaceutical or biological activity

The presence of these functional groups suggests that the compound may have potential pharmaceutical or biological activity.

Drug potential

The compound's structure indicates that it may have potential as a drug or as a precursor for the synthesis of other bioactive compounds.

Prodrug possibility

The presence of the nitro group suggests that the compound may have potential as a prodrug, which can be metabolized in the body to release an active pharmaceutical agent.

Further research needed

Additional research and investigation are necessary to fully understand the potential uses and properties of this compound.

Upstream product

• 1074-82-4 potassium phtalimide 
• 13551-86-5 α-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol 
• 136918-14-4 phthalimide 
• 13551-90-1 2-nitro-1-(2-oxiranylmethyl)-1H-imidazole 
• 527-73-1 2-nitro-1H-imidazole 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 

Relevant articles and documents

Preparation and biodistribution of technetium-99m-labeled bis-misonidazole (MISO) as an imaging agent for tumour hypoxia

Diagnosis of tumour hypoxia is an important aspect in determining the course of tumour therapy. In this study, we developed a novel imaging agent, 99mTcethylenedicysteine-bis-misonidazole (99mTc-EC-MISO), for diagnosing tumour hypoxia. We used 2-nitroimidazole as a reactant to synthesize the amino derivative of misonidazole (MISO) in the first step and then conjugated the di-amino derivative of MISO to the chelating agent ethylenedicysteine (EC) for labelling 99mTc in the second step. 99mTc-pertechnetate (99mTcO4-) was reduced by tin chloride (SnCl2) for radiolabeling. The radiochemical purity was up to 94%. Tissue biodistribution and SPECT/CT imaging studies were conducted on subcutaneous gliomal tumour-bearing mice. The tumour-to-muscle ratio in the 99mTc-EC-MISO group increased with time, up to 4.6 at 4 h after injection. SPECT/CT imaging confirmed that the tumours could be visualized clearly with 99mTc-EC-MISO at 2 h. By introducing a second 2-nitroimidazole redox centre, an apparent hypoxic accumulation of this novel 99mTc-labeled imaging agent in the tumour was observed.

Radiopharmaceutical formulations

A method is described for inhibiting the degradation of a diagnostic or radiotherapeutic radiopharmaceutical, especially radiolabeled compounds containing reducible moieties, by including oxidants either as a part of the composition for the preparation of such radiopharmaceuticals, or by adding an oxidant to such compositions immediately after the preparation of such radiopharmaceuticals.

Radiosensitizers of hypoxic mammalian cells. 1-(hydroxyaminoalkyl)-substituted nitroimidazoles

A series of novel 1-(hydroxyaminoalkyl)-substituted nitroimidazoles has been synthesized as potential radiosensitizers for hypoxic mammalian cells. These compounds were synthesized via N-(hydroxyalkyl)phthalimide nitroimidazole intermediates which, on reaction with hydrazine hydrate, yielded the corresponding amines. The intermediates were prepared by reacting the epoxide derived from nitroimidazole with phthalimide and/or the epoxide derived from phthalimide with the nitroimidazole. The method was used successfully for the preparation of 2-, 4- and 5-nitroimidazole derivatives. In a modification of this procedure, 1-(2-aminoethyl)-2-nitroimidazole has been prepared by a new route which avoids the use of aziridine. These agents were tested for cytotoxicity and radiosensitizing ability in vitro using Chinese hamster V79 cells. All of the 2-nitroimidazoles tested showed toxicity similar to that previously reported for misonidazole and Ro 03-8799 (1-(2-hydroxy-3-piperidinopropyl)-2-nitroimidazole), two compounds currently undergoing clinical evaluation. In addition, all the novel primary amines were shown to function as hypoxic cell radiosensitizers. The 2-nitroimidazole derivatives were the most efficient compounds to be examined and showed at least as much activity as misonidazole.