57531-37-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-4-nitroimidazole is used as a chemical intermediate for the preparation of antitubercular nitroimidazoles. These antitubercular agents are essential in the development of medications to treat tuberculosis, a severe and widespread bacterial infection.
Used in Oncology:
In the field of oncology, 2-Chloro-4-nitroimidazole serves as a radiosensitizer for hypoxic cells. Radiosensitizers are compounds that enhance the sensitivity of cancer cells to radiation therapy, making it more effective in destroying tumor cells, particularly those with low oxygen levels that are often more resistant to treatment. This application can improve the outcomes of cancer patients undergoing radiation therapy.

InChI:InChI=1/C3H2ClN3O2/c4-3-5-1-2(6-3)7(8)9/h1H,(H,5,6)

Upstream product

• 16265-04-6 2-chloro-1H-imidazole 
• 542-76-7 3-Chloropropionitrile 
• 5213-49-0 2,4-dinitro-1H-imidazole 
• 683276-47-3 2-bromo-1-methoxymethyl-4-nitroimidazole 
• 683276-67-7 2-chloro-5-iodo-4-nitroimidazole 
• 65902-59-2 2-bromo-4-nitro-1H-imidazole 

Downstream Products

• 86072-07-3 2-chloro-1-methyl-5-nitroimidazole 
• 63634-21-9 2-chloro-1-methyl-4-nitro-1H-imidazole 
• 92918-23-5 1-(2-Chloro-5-nitro-imidazol-1-yl)-propan-2-ol 
• 92918-22-4 1-(2-Chloro-4-nitro-imidazol-1-yl)-propan-2-ol 
• 73332-79-3 2-methyl-5-nitro-2,3-dihydro-imidazo[2,1-b]oxazole 
• 681490-95-9 (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-nitrobenzoyloxy)]-propyl-4-nitroimidazole 
• 681490-93-7 2-chloro-1-{[(2R)-2-methyloxiran-2-yl]methyl}-4-nitro-1H-imidazole 
• 943610-79-5 1-[3-(tert-butyl-dimethyl-silanyloxy)-2-(2-chloro-4-nitro-imidazol-1-ylmethyl)-propyl]-4-(4-trifluoromethoxy-phenyl)-piperazine 
• 1188337-65-6 1-(4-bromo-phenyl)-2-(2-chloro-4-nitro-imidazol-1-yl)-ethanone 
• 1188337-68-9 butyric acid (R)-3-{4-[2-(2-chloro-4-nitro-imidazol-1-yl)-acetyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester 
• 943610-74-0 C₁₈H₂₆ClN₃O₃Si 
• 1253202-36-6 (S)-3-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-(4-(trifluoro-methoxy)benzyloxy)propyl 4-methoxybenzoate 
• 1263188-33-5 1-(but-3-en-1-yl)-2-chloro-4-nitro-1H-imidazole 

Relevant academic research and scientific papers

PROCESS FOR PRODUCTION OF 2-CHLORO-4-NITROIMIDAZOLE DERIVATIVES

An improved process for preparing 2-chloro-4-nitroimidazole derivatives which are useful intermediates in the preparation of an anti-tuberculosis drug is provided. The process may comprise the step of chlorinating nitroimidazoles with a chlorinating agent and an activating agent to give 2-chloro-4-nitroimidazole derivatives.

Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions

Transition-metal-catalyzed programmed sequential arylation reactions of 2-chloro-4-nitro-1H-imidazoles were achieved. The methods are general and were applied in a chemoselective manner for the synthesis of different multiarylated 4-nitroimidazoles bearing three different aryl groups. A salient feature is Pd-catalyzed hetero-hetero coupling at the C5 position through a NO2 directed cross-dehydrogenative coupling (CDC) approach.

SUBSTITUTED 1,2,3-TRIAZOL-1-YL-METHYL-2,3-DIHYDRO-2-METHYL-6-NITROIMIDAZO[2,1-B]OXAZOLES AS ANTI-MYCOBACTERIAL AGENTS AND A PROCESS FOR THE PREPARATION THEREOF

The present invention relates to new generation of triazole functionality containing 6-nitro-2,3-dihydroimidazooxazole agents for general formula I, their method of preparation and their use as drugs for treatment of tuberculosis, MDR-TB and XDR-TB either

Preparation of 2-chloro-4-nitro imidazole method (by machine translation)

The invention discloses a method for preparing 2-chloro-4-nitroimidazole. The method comprises the following steps of reacting aminoacetaldehyde acetal with S-methyl-iso-thiourea sulphate to synthesise 2-aminoimidazole sulphate, and then performing diazotization reaction on 2-aminoimidazole sulphate and sodium nitrite; then performing chlorination reaction on a reactant obtained from the former step and cuprous chloride to obtain 2-chloro-imidazole; and finally performing nitration reaction with nitric acid to obtain 2-chloro-4-nitroimidazole. The synthesis method disclosed by the invention is capable of avoiding rearrangement and transposition, is moderate in reaction conditions, less in pollution, and easily realizes industrialized production.

Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: In vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation

The nitroimidazole scaffold has attracted great interest in the last decade, which ultimately led to the discovery of the successful drug Delamanid for multi-drug resistant tuberculosis (MDR-TB). Herein, we report medicinal chemistry on a 6-nitro-2,3-dihy

Design, synthesis, antibacterial evaluation and docking study of novel 2-hydroxy-3-(nitroimidazolyl)-propyl-derived quinolone

A novel series of 2-hydroxy-3-(nitroimidazolyl)-propyl-derived quinolones 6a-o were synthesized and evaluated for their in vitro antibacterial activity. Most of the target compounds exhibited potent activity against Gram-positive strains. Among them, moxifloxacin analog 6n displayed the most potent activity against Gram-positive strains including S. epidermidis (MIC = 0.06 μg/mL), MSSE (MIC = 0.125 μg/mL), MRSE (MIC = 0.03 μg/mL), S. aureus (MIC = 0.125 μg/mL), MSSA (MIC = 0.125 μg/mL), (MIC = 2 μg/mL). Its activity against MRSA was eightfold more potent than reference drug gatifloxacin. Finally, docking study of the target compound 6n revealed that the binding model of quinolone nucleus was similar to that of gatifloxacin and the 2-hydroxy-3-(nitroimidazolyl)-propyl group formed two additional hydrogen bonds. A novel series of 2-hydroxy-3-(nitroimidazolyl)-propyl derived quinolones 6a-o were synthesized and tested for their antibacterial activity. Moxifloxacin analog 6n showed potent activity against all tested strains (MIC = 0.03-2 μg/mL).

6-NITRO-2,3-DIHYDROIMIDAZO[2,1-b]OXAZOLES AND A PROCESS FOR THE PREPARATION THEREOF

The present invention relates to newer generation of triazoles, tetrazoles, isoxazoles, urea and sulphonamide functionalities containing 6-nitro-2, 3-dihydronitroimidazooxazoles agents of formula 1, their method of preparation, and their use as drugs for

METHODS FOR THE PRODUCTION OF 2-HALO-4-NITROIMIDAZOLE AND INTERMEDIATES THEREOF

The present invention relates to a method for the production of 2-halo-4-nitroimidazole and intermediates thereof. Further, the present invention relates to a production process of 1,4-dinitroimidazole comprising subjecting 4-nitroimidazole to nitration reaction. Furthermore, the present invention relates to a production process of 4-nitroimidazole comprising subjecting imidazole to nitration reaction.

PROCESS FOR PRODUCTION OF 2-CHLORO-4-NITROIMIDAZOLE

The present invention provides a process for production of 2-chloro-4-nitroimidazole in a high yield and at a high purity by a simple operation in a safer manner involving a low risk of explosion or the like. The present invention provides a process for production of 2-chloro-4-nitroimidazole represented by the formula (1): comprising a reaction of a 1-alkoxyalkyl-2-bromo-4-nitroimidazole compound represented by the general formula (7): wherein R1 represents a lower alkyl group, and n represents an integer of 1 to 3, with hydrogen chloride.

METHOD FOR PRODUCING 4-NITROIMIDAZOLE COMPOUND

The present invention provides a method for producing a 4-nitroimidazole compound represented by general formula (1) at high yield and at high purity by a safe method causing few dangers such as explosion. The production method of the present invention comprises iodinating a 4-nitroimidazole compound represented by general formula (2): wherein each of X1 and X2 represents a chlorine atom or bromine atom, and then reducing the obtained 5-iodo-4-nitroimidazole compound represented by general formula (3): wherein X2 is the same as defined above.