19182-81-1

Usage

Uses

Used in Chemical Synthesis Industry:
1,4-Dinitroimidazole is used as a chemical intermediate for the synthesis of various organic compounds and pharmaceuticals. Its unique structure and reactivity make it a valuable building block in the development of new molecules with potential applications in medicine and other fields.
Used in Research and Development:
1,4-Dinitroimidazole serves as a research compound in academic and industrial laboratories. It is used to study the properties and reactions of imidazoles and related compounds, contributing to the advancement of organic chemistry and the discovery of new materials and drugs.
Used in Manufacturing of Specialty Chemicals:
1,4-Dinitroimidazole is employed as a key component in the production of specialty chemicals, such as dyes, pigments, and other performance-enhancing additives. Its unique chemical properties allow it to impart specific characteristics to these products, improving their performance and functionality in various applications.

Upstream product

• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 288-32-4 1H-imidazole 

Downstream Products

• 143248-02-6 3-(4-Nitro-imidazol-1-yl)-benzoic acid 
• 208510-03-6 4(5)-nitro-1H-imidazole-5(4)-carbonitrile 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 24079-73-0 2,4,5-trinitroimidazole 
• 5213-49-0 2,4-dinitro-1H-imidazole 
• 220540-28-3 C₁₄H₁₆N₄O₄ 
• 220540-25-0 C₁₇H₂₀N₄O₃ 
• 342388-01-6 1-(3-methoxyphenyl)-4-nitro-1H-imidazole 
• 1185762-05-3 1-(2-methoxyphenyl)-4-nitro-1H-imidazole 
• 1178532-91-6 4-nitro-1-[(S)-1-phenylethyl]-1H-imidazole 
• 13230-13-2 1-benzyl-4-nitro-1H-imidazole 
• 1297345-05-1 butyl 4-(4-nitro-1H-imidazol-1-yl)benzoate 
• 1297345-30-2 butyl 2-chloro-5-(4-nitro-1H-imidazol-1-yl)benzoate 
• 1297345-21-1 1-(3-bromo-4-methylphenyl)-4-nitro-1H-imidazole 

Relevant academic research and scientific papers

2,4-Dinitroimidazole: Microwave Assisted Synthesis and Use in Synthesis of 2,3-Dihydro-6-nitroimidazo[2,1-b]oxazole Analogues with Antimycobacterial Activity

2,4-Dinitroimidazole (2,4-DNI), an important starting material for nitroimidazooxazole and nitroimidazooxazine types of antitubercular agents was synthesized by rearrangement of 1,4-dinitroimidazole (1,4-DNI) under microwave irradiation. Various new nitro

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).

High-energy-density materials based on 1-nitramino-2,4-dinitroimidazole

New energetic salts based on 1-nitramino-2,4-dinitroimidazole were successfully synthesized. The salts were fully characterized by 1H, 13C NMR and IR spectroscopy, differential scanning calorimetry (DSC), and elemental analyses. The salts were found to have good physical and detonation properties. The structure of guanidinium salt (3) was further confirmed by single-crystal X-ray diffraction. The densities of the energetic salts ranged between 1.70 and 1.93 g cm-3 as measured by a gas pycnometer. The detonation pressures and velocities calculated by the EXPLO5 code ranged within 29.3-40.5 GPa and 8370-9209 m s-1, respectively. The Royal Society of Chemistry 2013.

Transition-state variation in human, bovine, and Plasmodium falciparum adenosine deaminases

Adenosine deaminases (ADAs) from human, bovine, and Plasmodium falciparum sources were analyzed by kinetic isotope effects (KIEs) and shown to have distinct but related transition states. Human adenosine deaminase (HsADA) is present in most mammalian cells and is involved in B- and T-cell development. The ADA from Plasmodium falciparum (PfADA) is essential in this purine auxotroph, and its inhibition is expected to have therapeutic effects for malaria. Therefore, ADA is of continuing interest for inhibitor design. Stable structural mimics of ADA transition states are powerful inhibitors. Here we report the transition-state structures of PfADA, HsADA, and bovine ADA (BtADA) solved using competitive kinetic isotope effects (KIE) and density functional calculations. Adenines labeled at [6-13C], [6-15N], [6-13C, 6-15N], and [1-15N] were synthesized and enzymatically coupled with [1′-14C] ribose to give isotopically labeled adenosines as ADA substrates for KIE analysis. [6- 13C], [6-15N], and [1-15N]adenosines reported intrinsic KIE values of (1.010, 1.011, 1.009), (1.005, 1.005, 1.002), and (1.004, 1.001, 0.995) for PfADA, HsADA, and BtADA, respectively. The differences in intrinsic KIEs reflect structural alterations in the transition states. The [1-15N] KIEs and computational modeling results indicate that PfADA, HsADA, and BtADA adopt early SNAr transition states, where N1 protonation is partial and the bond order to the attacking hydroxyl nucleophile is nearly complete. The key structural variation among PfADA, HsADA, and BtADA transition states lies in the degree of N1 protonation with the decreased bond lengths of 1.92, 1.55, and 1.28 A, respectively. Thus, PfADA has the earliest and BtADA has the most developed transition state. This conclusion is consistent with the 20-36-fold increase of kcat in comparing PfADA with HsADA and BtADA.

Synthesis, thermal hazard analysis and density functional theory study of nitroimidazoles

To understand the thermal decomposition mechanism and performance of nitroimidazoles, 1,4-dinitroimidazole (1,4-DNI), 2,4-dinitroimidazole (2,4-DNI) and 4,5-dinitroimidazole (4,5-DNI) were synthesized by 4-nitroimidazole firstly and all of them were studied using Differential Scanning Calorimetry (DSC), Accelerating Rate Calorimetry (ARC) and Density Functional Theory (DFT). The experiments show that among the four nitroimidazoles, the decomposition temperature and apparent activation energy of 1,4-DNI are relatively low. Theoretical calculations show that compared with C[sbnd]NO2, N[sbnd]NO2 is easier to break from the imidazole ring, and the detonation performance of 1,4-DNI is the best among the four nitroimidazoles. Dinitroimidazoles all contain two nitro groups, resulting in their sensitivity and energy much greater than 4-NI. Since 1,4-DNI is the only substance containing N[sbnd]NO2, the chemical activity of 1,4-DNI is further improved. In addition, 1,4-DNI has relatively excellent detonation performance, which can be used as the research direction of new energetic materials.

WDR5-MYC INHIBITORS

Substituted N-heteroaryl sulfonamide compounds inhibit WDR5-MYC interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject such as cancer cell proliferation.

Discovery of WD Repeat-Containing Protein 5 (WDR5)-MYC Inhibitors Using Fragment-Based Methods and Structure-Based Design

The frequent deregulation of MYC and its elevated expression via multiple mechanisms drives cells to a tumorigenic state. Indeed, MYC is overexpressed in up to ?50% of human cancers and is considered a highly validated anticancer target. Recently, we discovered that WD repeat-containing protein 5 (WDR5) binds to MYC and is a critical cofactor required for the recruitment of MYC to its target genes and reported the first small molecule inhibitors of the WDR5-MYC interaction using structure-based design. These compounds display high binding affinity, but have poor physicochemical properties and are hence not suitable for in vivo studies. Herein, we conducted an NMR-based fragment screening to identify additional chemical matter and, using a structure-based approach, we merged a fragment hit with the previously reported sulfonamide series. Compounds in this series can disrupt the WDR5-MYC interaction in cells, and as a consequence, we observed a reduction of MYC localization to chromatin.

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.

Structure-Based Design of 6-Chloro-4-aminoquinazoline-2-carboxamide Derivatives as Potent and Selective p21-Activated Kinase 4 (PAK4) Inhibitors

Herein, we report the discovery and characterization of a novel class of PAK4 inhibitors with a quinazoline scaffold. Based on the shape and chemical composition of the ATP-binding pocket of PAKs, we chose a 2,4-diaminoquinazoline series of inhibitors as a starting point. Guided by X-ray crystallography and a structure-based drug design (SBDD) approach, a series of novel 4-aminoquinazoline-2-carboxamide PAK4 inhibitors were designed and synthesized. The inhibitors' selectivity, therapeutic potency, and pharmaceutical properties were optimized. One of the best compounds, 31 (CZh226), showed remarkable PAK4 selectivity (346-fold vs PAK1) and favorable kinase selectivity profile. Moreover, this compound potently inhibited the migration and invasion of A549 tumor cells by regulating the PAK4-directed downstream signaling pathways in vitro. Taken together, these data support the further development of 31 as a lead compound for PAK4-targeted anticancer drug discovery and as a valuable research probe for the further biological investigation of group II PAKs.

Highly efficient protocol for the aromatic compounds nitration catalyzed by magnetically recyclable core/shell nanocomposite

An efficient protocol for the nitration of aromatic compounds in the presence of a catalytic amount of sulfuric acid-functionalized silica-based magnetic core/shell nanocomposite was reported. The designed products were obtained in high yields in relatively short reaction times at room temperature under solvent-free conditions. The nanocatalyst was simply recovered from the reaction mixture by using an external magnet and efficiently reused for several times. The characterization of particle size, morphology and elemental analysis of the nanocatalyst were provided by scanning electron microscopy, transmission electron microscopy and energy-dispersive X-ray spectroscopy analyses, respectively.