6963-65-1

Usage

Uses

Used in Pharmaceutical and Chemical Research:
5-Bromo-4-nitro-1H-imidazole is utilized as a building block for the synthesis of various pharmaceuticals and bioactive compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Antimicrobial and Antifungal Applications:
Due to its antimicrobial and antifungal properties, 5-Bromo-4-nitro-1H-imidazole is considered a potential candidate for the development of new drugs to combat infections caused by bacteria and fungi. Its ability to inhibit the growth of these microorganisms can lead to the creation of effective treatments for various infections.
Used in Organic Synthesis:
5-Bromo-4-nitro-1H-imidazole is commonly employed as a versatile reagent in the field of organic synthesis. It is used for the introduction of the imidazole moiety into complex molecular structures, allowing for the creation of novel compounds with diverse applications in various industries.

InChI:InChI=1/C3H2BrN3O2/c4-2-3(7(8)9)6-1-5-2/h1H,(H,5,6)

Upstream product

• 7664-93-9 sulfuric acid 
• 2302-25-2 4-bromo-1 H-imidazole 
• 2302-25-2 5-bromo-1H-imidazole 
• 3034-38-6 5-nitro-1H-imidazole 
• 76529-48-1 4-Iodo-5-nitroimidazole 

Downstream Products

• 59177-47-8 4-bromo-1-methyl-5-nitro-1H-imidazole 
• 933-87-9 1-methyl-5-bromo-4-nitro-1H-imidazole 
• 6154-30-9 2,4⁽⁵⁾-dibromo-5⁽⁴⁾-nitroimidazole 
• 113121-60-1 4-nitro-5-phenylthioimidazole 
• 112995-51-4 5-bromo-4-nitro-1-phenacylimidazole 
• 68019-78-3 4⁽⁵⁾-Nitro-5⁽⁴⁾-methoxyimidazole 
• 113121-80-5 4-nitro-5-phenoxyimidazole 
• 113121-61-2 5-(4'-methylphenyl)thio-4-nitroimidazole 
• 57531-38-1 4-chloro-5-nitroimidazole 
• 657408-22-5 5-bromo-4-nitro-1-(3',5'-di-O-toluoyl-2'-deoxy-β-D-ribofuranosyl)imidazole 
• 4059-10-3 1-benzyl-5-bromo-4-nitroimidazole 
• 10512-70-6 1-(2,3,5-tri-O-acetyl-β-D-erythro-pentofuranosyl)-5-bromo-4-nitroimidazole 
• 87243-12-7 4⁽⁵⁾-Nitro-5⁽⁴⁾-phenylaminoimidazole 
• 132747-11-6 4-Bromo-5-nitro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole 

Relevant academic research and scientific papers

Synthesis, anti-HIV-1 and antiproliferative evaluation of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety

In an effort to synthesize more effective non-nucleoside reverse transcriptase inhibitors (NNRTIs) against the HIV-1 infection, a new series of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety were designed by molecular docking studies, prepared and characterized by spectroscopic techniques. All the synthesized compounds were in vitro evaluated for their inhibitory effect against the HIV-1 replication in the MT-4 cells. Results showed that none of these synthesized compounds displayed any specific anti HIV-1 activity. Surprisingly, these compounds showed high cytotoxicity against MT-4 cells with low selectivity index (50 = 1.3 μM and EC50 = 1.8 μM respectively).

Compounds containing 2-substituted imidazole ring for treatment against human African trypanosomiasis

A series of compounds containing 2-substituted imidazoles has been synthesized from imidazole and tested for its biological activity against human African trypanosomiasis (HAT). The 2-substituted 5-nitroimidazoles such as fexinidazole (7a) and 1-[4-(1-methyl-5-nitro-1H-imidazol-2-ylmethoxy)-pyridin-2- yl-piperazine (9e) exhibited potent activity against T. brucei in vitro with low cytotoxicity and good solubility. The presence of the NO2 group at the 5-position of the imidazole ring in 2-substituted imidazoles is the crucial factor to inhibit T. brucei.

Efficient Synthesis of DNA Containing the Guanine Oxidation-Nitration Product 5-Guanidino-4-nitroimidazole: Generation by a Postsynthetic Substitution Reaction

(Matrix presented) A convertible nucleoside was synthesized and used to prepare the 2′-deoxynucleoside of 5-guanidino-4-nitroimidazole, a putative in vivo product of the reaction of peroxynitrite with guanine. The convertible nucleoside was incorporated i

Anti-infective agents

Compounds having the formula are hepatitis C(HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C(HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

Anti-infective agents

Compounds having the formula are hepatitis C (HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C (HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

A novel nitroimidazole compound formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-guanosine

Peroxynitrite reacts with 2′,3′,5′-tri-O-acetyl-guanosine to yield a novel compound identified as 1-(2,3,5-tri-O-acetyl-β-D-erythro-pentofuranosyl) -5-guanidino-4-nitroimidazole (6). This characterization was achieved using a combination of UV/vis spectroscopy and ESI-MS. Additionally, 1 -(β-D-erythro-pentofuranosyl) 5-guanidino-4-nitroimidazole (6a) was synthesized by an independent route, characterized by UV/vis spectroscopy, ESI-MS, and 1H- and 13C NMR, and shown to be identical to deacetylated 6. This product is extremely stable in aqueous solution at both pH extremes and is formed in significant yields. These characteristics suggest that this lesion may be useful as a specific biomarker of peroxynitrite-induced DNA damage. We also observed formation of 2′,3′,5′-tri-O-acetyl-8-nitroguanosine (2′,3′,5′-tri-O-acetyl-8-NO2Guo), 2-amino-5-[(2,3,5 tri-O-acetyl-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one (2′,3′,5′-tri-O-acetyl-Iz), and the peroxy-nitrite-induced oxidation products of 2′,3′,5′-tri-O-acetyl-8-oxoGuo. The formation of 6 and 2′,3′,5′-tri-O-acetyl-8-NO2Guo was rationalized by a mechanism invoking formation of the guanine radical.