73332-75-9

Basic information

• Product Name: 2-Methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole
• Synonyms: 2-Methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole
• CAS NO: 73332-75-9
• Molecular Formula: C₆H₇N₃O₃
• Molecular Weight: 169.13808
• Mol File: 73332-75-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 333.7°C at 760 mmHg
• Flash Point: 155.6°C
• Appearance: /
• Density: 1.71g/cm³
• Vapor Pressure: 0.000135mmHg at 25°C
• Refractive Index: 1.72
• CAS DataBase Reference: 2-Methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole(73332-75-9)
• EPA Substance Registry System: 2-Methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole(73332-75-9)

Safety Data

• Hazardous Substances Data: 73332-75-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H7N3O3/c1-4-2-8-3-5(9(10)11)7-6(8)12-4/h3-4H,2H2,1H3

Upstream product

• 73332-73-7 1-(2,4-dinitro-imidazol-1-yl)-propan-2-ol 
• 75-56-9 methyloxirane 
• 5213-49-0 2,4-dinitro-1H-imidazole 

Relevant articles and documents

Synthesis and in vitro evaluation of new 5-substituted 6-nitroimidazooxazoles as antikinetoplastid agents

In continuation of our pharmacomodulation work on the nitroimidazooxazole series, we report the synthesis of new 5-substituted 6-nitroimidazooxazole derivatives. Our aim was to evaluate how functionalization of the 5-position of the 6-nitroimidazooxazole scaffold affects antileishmanial and antitrypanosomal in vitro activities. Twenty-one original compounds were synthesized and evaluated for their in vitro antileishmanial (L. donovani) and antitrypanosomal (T. cruzi) properties. Pallado-catalyzed cross-coupling reactions were used to introduce an aryl or ethynyl aryl substituent in 5-position from a 5-brominated-6-nitroimidazooxazole starting product. Unfortunately, the first series of compounds bearing an aryl group in 5-position presented limited in vitro activities against L. donovani and T. cruzi, with IC50 > 10 μM (vs 0.18 μM and 2.31 μM for the reference drugs amphotericin B and benznidazole respectively). Interestingly, the second series of compounds bearing an ethynyl aryl substituent in 5-position showed more promising, particularly against T. cruzi. Compounds 6a, 6b, 6c, 6g and 6h had better activity than the reference drug benznidazole (0.92 μM ≤ IC50 ≤ 2.18 μM vs IC50 = 2.31 μM), whereas the non-functionalized 2-methyl-6-nitro-2,3-dihydroimidazo [2,1-b]oxazole 2 was not active against T. cruzi (IC50 > 10 μM).

Nitroimidazoles XXI 2,3-dihydro-6-nitroimidazo[2,1-b]oxazoles with antitubercular activity

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Potential Radiosensitizing Agents. 2. Synthesis and Biological Activity of Derivatives of Dinitroimidazole with Oxiranes

A series of 1-substituted 2,4-dinitroimidazole analogues have been synthesized and tested for their radiosensitizing ability for selectively sensitizing hypoxic mammalian cells to the lethal effect of radiation.The reaction of 2,4(5)-dinitroimidazole (1) with a variety of oxiranes upon heating in absolute ethanol yielded the expected 1-substituted 2,4-dinitroimidazoles (2) and also resulted in the formation of a novel class of isomeric nitroimidazooxazoles (3 and 4) by intramolecular cyclization.The results of radiosensitizing activity of these agents against hypoxic Chinese hamster cells (V-79) indicated that 2,4-dinitroimidazoles were better sensitizers than the nitroimidazooxazoles, suggesting the necessity of the 2-nitro function in the molecule.The 1-(2-hydroxy-3-methoxypropyl)-2,4-dinitroimidazole (2d) was found to be the most effective radiosensitizer of this series.