88876-88-4

Basic information

• Product Name: 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol
• Synonyms: 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol;1-(2-NITRO-1-IMIDAZOYL)-3-(1-AZIRIDINYL)-2-PROPANOL;RSU-1069;NSC-347503;α-(1-Aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol
• CAS NO: 88876-88-4
• Molecular Formula: C₈H₁₂N₄O₃
• Molecular Weight: 212.208
• Mol File: 88876-88-4.mol

Chemical Properties

• Boiling Point: 474°C at 760 mmHg
• Flash Point: 240.5°C
• Appearance: /
• Density: 1.59g/cm³
• Vapor Pressure: 8.63E-10mmHg at 25°C
• Refractive Index: 1.704
• CAS DataBase Reference: 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol(88876-88-4)
• EPA Substance Registry System: 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol(88876-88-4)

Safety Data

• Hazardous Substances Data: 88876-88-4(Hazardous Substances Data)

Usage

Uses

Used in Ophthalmic Applications:
1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol is used as a therapeutic agent for conditions such as glaucoma and ocular hypertension. It is utilized for reducing intraocular pressure and increasing blood flow to the eye, which helps alleviate symptoms and prevent further damage to the optic nerve.
Used in Cardiovascular Applications:
In the cardiovascular industry, 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol is used as a medication to manage high blood pressure and reduce the workload on the heart. Its beta-blocking properties help control heart rate and blood vessel constriction, contributing to overall cardiovascular health and stability.
Used in Pharmaceutical Formulations:
1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol is incorporated into various pharmaceutical formulations as an active ingredient. It is used for its combined effects of beta blockade and vasodilation, making it suitable for treating a range of conditions that involve high blood pressure and compromised blood flow.

InChI:InChI=1/C8H12N4O3/c13-7(5-10-3-4-10)6-11-2-1-9-8(11)12(14)15/h1-2,7,13H,3-6H2

Synthetic route

sodium hydrogencarbonate (144-55-8) + α-<<(2-bromoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol monohydrobromide (129448-97-1) → NSC 347503 (88876-88-4) + 3-<2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl>-2-oxazolidinone (129449-06-5)

Conditions	Yield
With phosphate-buffered saline (PBS, Oxoid) In water at 23℃; Product distribution; other <(haloethyl)amino>propyl-2-nitroimidazoles; pH 7.0 - 7.5;

α-<<(2-bromoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol monohydrobromide (129448-97-1) → NSC 347503 (88876-88-4)

Conditions	Yield
With triethylamine In various solvent(s) at 25℃; for 0.5h;

3-<2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl>-2-oxazolidinone (129449-06-5) → NSC 347503 (88876-88-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / 31percent HBr, HOAc / 20.3 h / Ambient temperature 2: Et3N / various solvent(s) / 0.5 h / 25 °C View Scheme

(R,S)-3-(oxiranylmethyl)-2-oxazolidinone (21899-19-4) → NSC 347503 (88876-88-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Cs2CO3 / 1.) EtOH, reflux, 20 min, 2.) reflux, 6 h 2: 54 percent / 31percent HBr, HOAc / 20.3 h / Ambient temperature 3: Et3N / various solvent(s) / 0.5 h / 25 °C View Scheme

NSC 347503 (88876-88-4) → α-<<(2-bromoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol monohydrobromide (129448-97-1)

Conditions	Yield
With hydrogen bromide In acetone at 5 - 10℃;	96%

NSC 347503 (88876-88-4) → α-<<(2-chloroethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydrochloride (129448-96-0)

Conditions	Yield
With hydrogenchloride In acetone at 5 - 10℃; for 0.0333333h;	93%

NSC 347503 (88876-88-4) → α-<<(2-iodoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydriodide (129448-98-2)

Conditions	Yield
With hydrogen iodide In acetone at 0 - 5℃; for 0.0833333h;	51%

NSC 347503 (88876-88-4) → α-<<(2-fluoroethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydrochloride (129448-99-3)

Conditions	Yield
With hydrogenchloride; hydrogen fluoride In acetone at 0 - 5℃; for 0.0833333h;	41%

Upstream product

• 21899-19-4 (R,S)-3-(oxiranylmethyl)-2-oxazolidinone 
• 129448-97-1 α-<<(2-bromoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol monohydrobromide 
• 144-55-8 sodium hydrogencarbonate 
• 129449-06-5 3-<2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl>-2-oxazolidinone 

Downstream Products

• 129448-98-2 α-<<(2-iodoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydriodide 
• 129448-96-0 α-<<(2-chloroethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydrochloride 
• 129448-97-1 α-<<(2-bromoethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol monohydrobromide 

Relevant articles and documents

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.