7464-68-8

Usage

Uses

Used in Pharmaceutical Industry:
1,5-Dimethyl-4-nitro-1H-imidazole is used as a potential pharmaceutical compound for its possible biological activities. Given its structure and the presence of the nitro group, it may exhibit properties that could be harnessed for therapeutic applications, although further research is needed to explore its potential in this field.
Used in Chemical Research:
1,5-Dimethyl-4-nitro-1H-imidazole is used as a subject of study in chemical research to understand its reactivity and potential interactions with other compounds. The nitro group's chemical properties may lead to interesting reactions and transformations, making it a valuable compound for exploring new chemical pathways and mechanisms.
Used in Material Science:
1,5-Dimethyl-4-nitro-1H-imidazole may be used as a component in the development of new materials, particularly in areas where its chemical reactivity and structural properties could contribute to the creation of novel materials with unique properties. Its potential use in material science would require a thorough understanding of its chemical behavior and compatibility with other materials.

InChI:InChI=1/C5H7N3O2/c1-4-5(8(9)10)6-3-7(4)2/h3H,1-2H3

Upstream product

• 10447-93-5 1,2-dimethylimidazole 
• 14003-66-8 4-methyl-5-nitro-1H-imidazole 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 14003-66-8 5-methyl-4-nitro-1H-imidazole 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 3034-41-1 1-methyl-4-nitro-1H-imidazole 
• 25554-84-1 2-(ethoxycarbonothioylthio)acetic acid 
• 20041-97-8 2-(1-methyl-4-nitro-1H-imidazol-5-yl)acetic acid 

Downstream Products

• 87471-08-7 (E)-1-methyl-4-nitro-5-(2-phenylethenyl)-1H-imidazole 
• 600-21-5 N-methylalanine 
• 871885-96-0 1,5-dimethyl-1H-imidazol-4-ylamine 
• 1456787-32-8 (E)-2-bromo-1-methyl-4-nitro-5-styryl-1H-imidazole 
• 1456787-33-9 (E)-1-methyl-4-nitro-5-styryl-1H-imidazole-2-carbonitrile 
• 1017279-02-5 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole 
• 1245555-18-3 (2E)-4-{[4-(3-bromoanilino)-6-quinazolinyl]amino}-N,N-dimethyl-N-[(1-methyl-4-nitro-1H-imidazol-5-yl)methyl]-4-oxo-2-buten-1-ammonium bromide 

Relevant academic research and scientific papers

Inexpensive Radical Methylation and Related Alkylations of Heteroarenes

A simple method for the introduction of a methyl and higher aliphatic group to various heteroarenes using very inexpensive reagents is described. It is based on the radical addition of a carboxylic xanthate followed by decarboxylation. Depending on the heteroarene structure, the decarboxylation can be spontaneous or induced by heating in N,N-dimethylacetamide or N-methyl pyrrolidone in a microwave oven.

Synthesis of substituted 5-bromomethyl-4-nitroimidazoles and use for the preparation of the hypoxia-selective multikinase inhibitor SN29966

5-Bromomethyl-4-nitroimidazoles have utility as bioreductive trigger precursors for the preparation of hypoxia-selective prodrugs. Here we describe an efficient two-step synthesis of 5-(bromomethyl)-1-methyl-4-nitro-1H- imidazole, a preferred precursor, employing an N-bromosuccinimide mediated radical bromination. Use of this precursor to prepare SN29966, a promising hypoxia-selective irreversible pan-ErbB inhibitor is reported along with the preparation of four other prodrug candidates. 5-Bromomethyl-4-nitroimidazole analogues bearing electron-donating and electron-withdrawing substituents at the N-1 and C-2 positions are also described.

PRODRUG FORMS OF KINASE INHIBITORS AND THEIR USE IN THERAPY

The invention provides novel prodrug compounds comprising a kinase inhibitor and a reductively-activated fragmenting aromatic nitroheterocycle or aromatic nitrocarbocycle trigger, where the compound carries a positive charge. In preferred embodiments, the compounds are of Formula I: where: X is any negatively charged counterion; R1 is a group of the formula —(CH2)nTr, where Tr is an aromatic nitroheterocycle or aromatic nitrocarbocycle and —(CH2)nTr acts as a reductively-activated fragmenting trigger; and n is an integer from 0 to 6; R2, R3 and R4 may each independently be selected from aliphatic or aromatic groups of a tertiary amine kinase inhibitor (R2)(R3)(R4)N, or two of R2, R3, and R4 may form an aliphatic or aromatic heterocyclic amine ring of a kinase inhibitor, or one of R2, R3 and R4 may be absent and two of R2, R3 and R4 form an aromatic heterocyclic amine ring of a kinase inhibitor. The compounds of the invention are useful in treating proliferative diseases such as cancer.

Carbanion Stabilization in C,N-Dimethylnitroimidazoles

Kinetics of base-catalyzed exchange of C-methyl protons have been investigated for the six position isomers of C,N-dimethylnitroimidazoles (at 60 deg C in D2O-CD3OD, 1:1).Rates of exchange were based on the decrease in 1H NMR signals relative to those for the nonexchanging N-methyl groups.Values of kOD covered a range of 5*104; in 0.01 N NaOD, values of t1/2 range from 2.8 s to 38 h.The greatest kinetic acidity was found in 1,5-dimethyl-4-nitroimidazole and the least in 1,2-dimethyl-4-nitro- and 1,4-dimethyl-2-nitroimidazole.In the latter two compounds, the methyl and nitro groups have a "meta" relationship, their resistance to exchange indicates weak resonance stabilization of the respective carbanions.The value of kOD for 1,5-dimethyl-4-nitroimidazole (1485 M-1 min-1) is 4.8*106 as great as that for o-nitrotoluene but only 27-fold less than that for nitromethane.The result suggests that there may be significant localization in the 4,5-double bond of N-substituted imidazoles.The order of kinetic acidities for the C-methyl groups is consistent with the order of reactivities of the same compounds in aldol condensations.