22813-32-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-NitroiMidazol-1-yl)acetic acid is used as a potential therapeutic agent for its antimicrobial, antifungal, and antitumor properties. It is likely to be employed in the development of new drugs that target various diseases and conditions, given its ability to interact with proteins and cellular molecules within the body.
Used in Antimicrobial Applications:
2-(2-NitroiMidazol-1-yl)acetic acid is used as an antimicrobial agent to combat bacterial infections. Its imidazole-based structure allows it to interfere with essential microbial processes, thereby inhibiting the growth and proliferation of bacteria.
Used in Antifungal Applications:
2-(2-NitroiMidazol-1-yl)acetic acid is used as an antifungal agent to treat fungal infections. Its imidazole derivative nature enables it to target and disrupt the cellular functions of fungi, effectively controlling their growth and spread.
Used in Antitumor Applications:
2-(2-NitroiMidazol-1-yl)acetic acid is used as an antitumor agent in cancer therapy. Its potential to interact with proteins and cellular molecules may allow it to inhibit tumor growth and progression, making it a candidate for further research and development in oncology.

InChI:InChI=1/C5H5N3O4/c9-4(10)3-7-2-1-6-5(7)8(11)12/h1-2H,3H2,(H,9,10)

Upstream product

• 5006-67-7 2-(2-nitro-1H-imidazol-1-yl)-ethanol 
• 22668-01-5 etanidazole 
• 127894-74-0 tert-butyl 2-(2-nitro-1H-imidazol-1-yl)acetate 
• 22813-31-6 methyl 2-(2-nitro-1H-imidazole-1-yl)acetate 

Downstream Products

• 199734-70-8 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl)acetate 
• 1383370-94-2 2-(2-nitro-imidazol-1-yl)-N-(4-sulfamoylphenyl)acetamide 
• 199800-19-6 FETA 
• 154094-89-0 N-[2-(2-methyl-5-nitro-1H-imidazolyl)ethyl]-2-(2-nitro-1H-imidazolyl)ethanamide 
• 131339-74-7 1-(t-butoxycarbonyl)-4-(2-nitroimidazol-1-ylacetyl)piperazine 
• 1383370-96-4 2-(2-nitro-imidazol-1-yl)-N-[2-(4-sulfamoylphenyl)ethyl]-acetamide 
• 1383370-95-3 2-(2-nitro-imidazol-1-yl)-N-(4-sulfamoylbenzyl)acetamide 

Relevant academic research and scientific papers

Oxazolidine Formation, or Loss of Acid, from Attempted Fluorination of Amide Side-Chain in 2-Nitroimidazoles

Reaction of Etanidazole (a 2-nitroimidazole derivative with an amide side-chain containing a hydroxyethyl group) with triflic anhydride gives, depending on conditions, a trifluoromethyl(sulfonyl)oxazolidine via a cyclization reaction, or a fluorine-free formate derivative; reaction with tosyl chloride gives only a chloroethyl derivative. An attempt to replace a Br-atom in a related propyl-containing amide side-chain by a F-atom forms instead a propylene derivative via loss of HBr. The studies stem from interest in use of 2-nitroimidazoles with fluorine-containing amide side-chains as hypoxia markers.

Anilinoquinazoline compound containing nitroimidazole group and preparation method and application thereof

The invention provides a brand new anilinoquinazoline compound of the structure in the formula (I). The anilinoquinazoline compound has a tyrosine kinase inhibiting effect. Real-time fluorogenic quantitative PCR measurement results indicate that the VEGF

Design and synthesis of vandetanib derivatives containing nitroimidazole groups as tyrosine kinase inhibitors in normoxia and hypoxia

Sixteen novel epidermal growth factor receptor (EGFR)/vascular endothelial growth factor (VEGF)-2 inhibitors (nitroimidazole-substituted 4-anilinoquinazoline derivatives (16a-p)) were designed and prepared via the introduction of a nitroimidazole group in the piperidine side chain and modification on the aniline moiety of vandetanib. Preliminary biological tests showed that comparing with vandetanib, some target compounds exhibited excellent EGFR inhibitory activities and anti-proliferative over A549/H446 cells in hypoxia. Meanwhile, several of the above compounds demonstrated better bioactivity than vandetanib in VEGF gene expression inhibition. Owing to the excellent IC50 value (1.64 μmol/L), the inhibition ratios of 16f over A549 and H446 cells were 62.01% and 59.86% at the concentration of 0.5 μM in hypoxia, respectively. All of these results indicated that 16f was a potential cancer therapeutic agent in hypoxia and was worthy of further development.

Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates

A series of nitroimidazoles incorporating sulfonamide/sulfamide/sulfamate moieties were designed and synthesized as radio/chemosensitizing agent targeting the tumor-associated carbonic anhydrase (CA) isoforms IX and XII. Most of the new compounds were nanomolar inhibitors of these isoforms. Crystallographic studies on the complex of hCA II with the lead sulfamide derivative of this series clarified the binding mode of this type of inhibitors in the enzyme active site cavity. Some of the best nitroimidazole CA IX inhibitors showed significant activity in vitro by reducing hypoxia-induced extracellular acidosis in HT-29 and HeLa cell lines. In vivo testing of the lead molecule in the sulfamide series, in cotreatment with doxorubicin, demonstrated a chemosensitization of CA IX containing tumors. Such CA inhibitors, specifically targeting the tumor-associated isoforms, are candidates for novel treatment strategies against hypoxic tumors overexpressing extracellular CA isozymes.

Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds

The syntheses of new nitroimidazole compounds using silicon-[ 18F]fluorine chemistry for the potential detection of tumor hypoxia are described. [18F]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/μmol, however these compounds ([18F]7 and [18F]11) were not stable in plasma. Phenyldi-tert-butyl compounds were labeled in 70% yield with a specific activity of 3 GBq/μmol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/μmol. The labeled compound [18F]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-butyl (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [ 18F]18 is suitable for further in vivo assessments.

CANCER TARGETING USING CARBONIC ANHYDRASE ISOFORM IX INHIBITORS

The present invention concerns novel carbonic anhydrase IX inhibitors comprising a nitroimidazole moiety and their use in therapy of hypoxic conditions, in particular cancer treatment, especially chemotherapy and radiotherapy. The compounds of the invention have an increased specificity for the carbonic anhydrase IX enzyme compared to the art. The present invention relates to novel nitroimidazole derivates represented by formula (1).

Hypoxia-selective antitumor agents. 8. Bis(nitroimidazolyl)alkanecarboxamides: A new class of hypoxia-selective cytotoxins and hypoxic cell radiosensitisers

A series of novel bis(nitroimidazolyl)alkanecarboxamides has been prepared and evaluated for hypoxia-selective cytotoxicity and hypoxic cell radiosensitisation in vitro and in vivo. The compounds were prepared by direct coupling of preformed side chain acid and amine components, using diethyl phosphorocyanidate at room temperature. Although designed to be bis- bioreductive prodrugs of DNA cross-linking agents, none of the compounds showed evidence of DNA cross-linking activity, being equally potent against cell lines deficient and proficient in repair of cross-links. However, one of these compounds, N-[2-(2-methyl-5-nitro-1H-imidazolyl)ethyl]-4-(2-nitro-1H- imidazolyl)butanamide (10; SN 24699), showed high hypoxic selectivity as a cytotoxin (rising to 200-fold after exposure to the drug for several hours) in the repair-proficient Chinese hamster cell line AA8. This selectivity was greater than observed for the alkylating 2-nitroimidazole (4; RB 6145) (40- fold) or simple mononitroimidazoles (5-25-fold). Investigation of structure- activity relationships for hypoxic selectivity of bis(nitroimidzoles) was restricted by their low aqueous solubility, but a certain minimum separation of the two nitroimidazole units (by more than five atoms) appears desirable. All the compounds radiosensitized hypoxic cells in vitro but were little more potent as radiosensitizers than the corresponding monomeric nitroimidazoles. Compound 10 caused additional cell killing in the KHT tumor when multiple drug doses were administered in combination with a single dose of radiation. It is not yet clear whether this activity reflects hypoxic cell radiosensitization or cytotoxicity toward hypoxic cells, but this new class of bis-bioreductive agent clearly warrants further investigation.