115398-63-5

Basic information

• Product Name: 1-(3-Bromopropyl)-2-nitro-1H-imidazole
• Synonyms: 1-(3-Bromopropyl)-2-nitro-1H-imidazole;1-(3-bromopropyl)-2-nitroimidazole
• CAS NO: 115398-63-5
• Molecular Formula: C₆H₈BrN₃O₂
• Molecular Weight: 234.05062
• Mol File: 115398-63-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(3-Bromopropyl)-2-nitro-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Bromopropyl)-2-nitro-1H-imidazole(115398-63-5)
• EPA Substance Registry System: 1-(3-Bromopropyl)-2-nitro-1H-imidazole(115398-63-5)

Safety Data

• Hazardous Substances Data: 115398-63-5(Hazardous Substances Data)

Usage

General Description

1-(3-Bromopropyl)-2-nitro-1H-imidazole is a chemical compound that belongs to the class of nitroimidazoles. It is commonly used in medicinal and pharmaceutical applications due to its potential antimicrobial and antiprotozoal properties. The presence of the bromopropyl and nitro groups in the chemical structure makes it a versatile compound for various chemical reactions and synthesis processes. Its ability to selectively target and inhibit the growth of certain microorganisms makes it a valuable component in drug development for the treatment of infections caused by bacteria and parasites. Additionally, its potential for further functionalization and modification adds to its importance in organic chemistry and drug discovery research.

Upstream product

• 527-73-1 2-nitro-1H-imidazole 
• 109-64-8 1,3-dibromo-propane 
• 109-70-6 1.3-chlorobromopropane 

Downstream Products

• 1214889-84-5 N-[3-(3-fluoro-4-{4-[3-(2-nitro-imidazol-1-yl)-propyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide 

Relevant articles and documents

Synthesis of Mitochondria-Anchored Nitroimidazoles with a Versatile NIR Fluorophore for Hypoxic Tumor-Targeting Imaging and Chemoradiotherapy

Nitroimidazoles are one of the most common radiosensitizers investigated to combat hypoxia-induced resistance to cancer radiotherapy. However, due to poor selectivity distinguishing cancer cells from normal cells, effective doses of radiosensitization are much closer to the doses of toxicity induced by nitroimidazoles, limiting their clinical application. In this work, a tumor-targeting near-infrared (NIR) cyanine dye (IR-808) was utilized as a targeting ligand and an NIR fluorophore tracer to chemically conjugate with different structures of hypoxia-affinic nitroimidazoles. One of the NIR fluorophore-conjugated nitroimidazoles (808-NM2) was identified to preferentially accumulate in hypoxic tumor cells, sensitively outline the tumor contour, and effectively inhibit tumor growth synergistically by chemotherapy and radiotherapy. More importantly, nitroimidazoles were successfully taken into cancer cell mitochondria via 808-NM2 conjugate to exert the synergistic effect of chemoradiotherapy. Regarding the important roles of mitochondria on cancer cell survival and metastasis under hypoxia, 808-NM2 may be hopeful to fight against hypoxic tumors.

Modulation of in vivo distribution through chelator: Synthesis and evaluation of a 2-nitroimidazole-dipicolylamine-99mTc(CO)3 complex for detecting tumor hypoxia

Previous studies have clearly demonstrated strong correlation between in vivo distribution and blood clearance of radiopharmaceuticals for the detection of hypoxia. Present study describes an attempt to improve the in vivo distribution of a previously reported 2-nitroimidazole-99mTc(CO)3 complex by tuning its blood clearance pattern through structural modification of the ligand. Herein, a 2-nitroimidazole-dipicolylamine ligand (2-nitroimidazole-DPA) was synthesized in a two-step procedure and radiolabeled with 99mTc(CO)3 core. Subsequently, the complex was evaluated in Swiss mice bearing fibrosarcoma tumor. As intended by its design, 2-nitroimidazole-DPA-99mTc(CO)3 complex was more lipophilic than previously reported 2-nitroimidazole-DETA-99mTc(CO)3 complex (DETA - diethylenetriamine) and showed slower blood clearance. Consequently it showed higher tumor uptake than 2-nitroimidazole-DETA-99mTc(CO)3 complex. Significantly, despite structural modifications, other parameters such as the tumor to blood ratio and tumor to muscle ratio of the 2-nitroimidazole-DPA-99mTc(CO)3 complex remained comparable to that of 2-nitroimidazole-DETA-99mTc(CO)3 complex. Present study demonstrates the feasibility of structural modifications for improving in vivo tumor uptake of hypoxia detecting radiopharmaceuticals. This might encourage researchers to improve suboptimal properties of a potential radiopharmaceuticals rather than ignoring it altogether.

Tripterine imidazole derivative as well as preparation method and application thereof

The invention discloses a novel tripterine imidazole derivative as well as a preparation method and application thereof, and belongs to the field of biomedicine. The tripterine imidazole derivative has a structure shown as a formula I as shown in the specification, wherein R1, R2 and R3 are respectively selected from H, alkyl, hetero-atomic alkyl, halogen or nitryl; and X is selected from a saturated or unsaturated linear aliphatic hydrocarbon fragment containing 3-6 carbon atoms. The novel tripterine imidazole derivative as well as the preparation method and the application thereof disclosedby the invention have the benefits that the preparation method of the compound is mild in reaction conditions; a used reagent is low in toxicity, raw materials are easy to obtain, the post-treatment is convenient, and the yield is relatively high. Pharmacological experiment studies shows that the compound has excellent anti-tumor activity and can be applied to the preparation of an anti-tumor drug.