153667-41-5

Basic information

• Product Name: (2R)-1-[(2-bromoethyl)amino]-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol hydrobromide (1:1)
• CAS NO: 153667-41-5
• Molecular Formula: C₈H₁₄Br₂N₄O₃
• Molecular Weight: 374.0298
• Mol File: 153667-41-5.mol

Chemical Properties

• Boiling Point: 527.5°C at 760 mmHg
• Flash Point: 272.8°C
• Vapor Pressure: 5.9E-12mmHg at 25°C
• CAS DataBase Reference: (2R)-1-[(2-bromoethyl)amino]-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol hydrobromide (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-1-[(2-bromoethyl)amino]-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol hydrobromide (1:1)(153667-41-5)
• EPA Substance Registry System: (2R)-1-[(2-bromoethyl)amino]-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol hydrobromide (1:1)(153667-41-5)

Safety Data

• Hazardous Substances Data: 153667-41-5(Hazardous Substances Data)

Upstream product

• 153656-02-1 (R)-α-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol 
• 153656-01-0 (S)-α-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol 
• 129449-06-5 3-<2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl>-2-oxazolidinone 
• 99464-91-2 α-<<(2-hydroxyethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol 
• 88876-88-4 NSC 347503 
• 157928-73-9 (S)-3-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone 
• 153656-04-3 (R)-2-nitro-1-(2-oxiranylmethyl)-1H-imidazole 
• 157928-70-6 (R)-3-[3-(2-Nitro-1H-imidazol-1-yl)-2-[(trimethylsilyl)oxy]propyl]-2-oxazolidinone 
• 153656-03-2 (S)-2-nitro-1-(2-oxiranylmethyl)-1H-imidazole 
• 157928-72-8 (S)-3-[3-(2-nitro-1H-imidazol-1-yl)-2-[(trimethylsilyl)oxy]propyl]-2-oxazolidinone 
• 21899-19-4 (R,S)-3-(oxiranylmethyl)-2-oxazolidinone 

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.

Potentiation of bioreductive agents

A human or animal subject having a solid tumour is treated by administering to the subject therapeutically effective amounts of a nitric oxide (NO) synthase inhibitor and a compound which is an imidazole or 1,2,4-triazole derivative of formula (A) STR1 wherein X is selected from the group consisting of STR2 wherein R is hydrogen or a C 1 -C 6 alkyl group; each of R'' 1 to R'' 5 is independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, hydroxy(C 1 -C 6 alkyl), phenyl, (C 1 -C 6 alkyl)phenyl and phenyl(C 1 -C 6 alkyl); m is 0 or 1; n is 1 or 2; and Z'' represents a leaving group which has the potential for expulsion via an intramolecular cyclisation reaction and which is not negatively-charged; or a physiologically acceptable acid addition salt thereof.

Process for preparing chiral [[(2-bromoethyl)-amino]methyl]-2-nitro-1H-imidazol-1-ethanol and related compounds

Chiral compounds useful as radiosensitizers or chemosensitizers having the formula STR1 wherein X is halogen or STR2 intermediates used to prepare these compounds, and a novel process to prepare these compounds are described.

Nitro-substituted aromatic or hetero-aromatic compounds for use in cancer treatment

A compound for treating a patient having a solid tumor in which it is known or suspected that hypoxic cells are present, which is a compound of formula (A): STR1 wherein X represents a nitro-substituted aromatic or hetero-aromatic group with a one-electron reduction potential at pH 7 of from -250 to -500 mV; each of R'1 to R'5 independently represents hydrogen or an alkyl, hydroxyalkyl, aryl, aralkyl or alkaryl group; m is 0 or 1; n is 1 or 2; and Z' represents a leaving group which has the potential for expulsion via an intramolecular cyclization reaction; or a physiologically acceptable acid addition salt thereof.

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.