129449-06-5

Basic information

• Product Name: 3-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)-2-oxazolidinone
• Synonyms: 3-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)-2-oxazolidinone
• CAS NO: 129449-06-5
• Molecular Formula: C₉H₁₂N₄O₅
• Molecular Weight: 0
• Mol File: 129449-06-5.mol

Chemical Properties

• Boiling Point: 655°Cat760mmHg
• Flash Point: 349.9°C
• Appearance: /
• Density: 1.67g/cm³
• Vapor Pressure: 4.75E-18mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 3-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)-2-oxazolidinone(129449-06-5)
• EPA Substance Registry System: 3-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)-2-oxazolidinone(129449-06-5)

Safety Data

• Hazardous Substances Data: 129449-06-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H12N4O5/c14-7(6-12-3-4-18-9(12)15)5-11-2-1-10-8(11)13(16)17/h1-2,7,14H,3-6H2

Upstream product

• 527-73-1 2-nitro-1H-imidazole 
• 21899-19-4 (R,S)-3-(oxiranylmethyl)-2-oxazolidinone 
• 144-55-8 sodium hydrogencarbonate 
• 129448-97-1 α-<<(2-bromoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol monohydrobromide 

Downstream Products

• 129448-97-1 α-<<(2-bromoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol monohydrobromide 
• 131504-98-8 Benzoic acid 1-[(2-bromo-ethylamino)-methyl]-2-(2-nitro-imidazol-1-yl)-ethyl ester; hydrobromide 
• 88876-88-4 NSC 347503 

Relevant articles and documents

Synthesis of the enantiomers of the dual function 2-nitroimidazole radiation sensitizer RB 6145

Short, efficient pathways are described for the synthesis of racemic 2-nitroimidazole radiation sensitizer RB-6145 (2a) and each of its corresponding (R)- and (S)-enantiomers (2b and 2c, respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3-trimethylsilyl-2-oxazolidinone (3b) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the (R)-enantiomer (2b) has been successfully scaled up to provide multi-kilo quantities of material for early stage preclinical evaluation.

Dual-Function Radiosensitizers. α-methyl>-2-nitro-1H-imidazole-1-ethanol and Related Compounds: Preparation via an Aziridine Equivalent

An improved synthesis of the dual-function radiosensitizer α-methyl>-2-nitro-1H-imidazole-1-ethanol (2, RB 6145) has been developed.Previously, the synthetic difficulties associated with this compound limited its attractiveness as a clinical candidate, although its radiosensitizing activity in preclinical models warranted its further development.The synthesis described uses a 2-oxazolidinone as an aziridine equivalent and provides 2 in 47 percent yield.

Synthesis and Evaluation of α-methyl>-2-nitro-1H-imidazole-1-ethanols as Prodrugs of α--2-nitro-1H-imidazole-1-ethanol (RSU-1069) and Its Analogues Which Are Radiosensitizers and Bioreductively Activated Cytotoxins

α--2-nitro-1H-imidazole-1-ethanols, of general formula , where Im = 2-nitroimidazole and R1, R2, R3, R4 = H, Me, are radiosensitizers and selective bioreductively activated cytotoxins toward hypoxic tumor cells in vitro and in vivo.Treatment of the aziridines with hydrogen halide in acetone or aqueous acetone gave the corresponding 2-haloethylamines of general formula ImCH2CH(OH)CH2+-NH2CR1R2CR3R4XX-, where R1, R2, R3, R4 = H, Me, and X = F, Cl, Br, I.These 2-haloethylamines were evaluated as prodrugs of the parent aziridines.The rates of ring closure in aqueous solution at pH ca. 6 were found to increase with increasing methyl substitution and to depend on the nature of the leaving group (I ca.Br > Cl >> F).A competing reaction of ImCH2CH(OH)CH2+NH2CH2CH2XX- (X = Cl, Br) with aqueous HCO3- ions gives 3--2-oxazolidinone.The activities of these prodrugs as radiosensitizers or as bioreductively activated cytotoxins were consistent with the proportion converted to the parent aziridine during the course of the experiment. α-methyl>-2-nitro-1H-imidazole-1-ethanol (RB 6145, 10), the prodrug of α--2-nitro-1H-imidazole-1-ethanol (RSU-1069, 3), is identified as the most useful compound in terms of biological activity and rate of ring closure under physiological conditions.