50365-37-2

Usage

Uses

Used in Pharmaceutical Industry:
5,6-DINITROBENZIMIDAZOLE is used as an inhibitor for milk xanthine oxidase due to its potent inhibitory properties. This application is particularly relevant in the development of drugs targeting xanthine oxidase-related conditions, such as gout and certain types of cancer.
Used in Biochemical Research:
In the field of biochemistry, 5,6-DINITROBENZIMIDAZOLE serves as a valuable research tool for studying the function and regulation of xanthine oxidase. Its ability to inhibit the enzyme can help researchers understand the underlying mechanisms of various diseases and conditions associated with xanthine oxidase activity.
Used in Chemical Synthesis:
As a member of the benzimidazole family, 5,6-DINITROBENZIMIDAZOLE can be utilized as a starting material or intermediate in the synthesis of other related compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C7H4N4O4/c12-10(13)6-1-4-5(9-3-8-4)2-7(6)11(14)15/h1-3H,(H,8,9)

Upstream product

• 94-52-0 5-nitrobenzimidazole 
• 64-18-6 formic acid 
• 32690-28-1 4,5-dinitro-1,2-phenylenediamine 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 94-52-0 6-nitro-1H-benzo[d]imidazole 
• 51-17-2 benzoimidazole 

Downstream Products

• 90000-54-7 1H-benzimidazole-5,6-diyldiamine; dihydrochloride 
• 619327-49-0 5,6-diamino-1-methylbenzimidazole 
• 71209-21-7 5,6-diaminobenzimidazole 
• 116204-49-0 2-methyl-1,5-dihydro-benzo[1,2-d;4,5-d']diimidazole 

Relevant academic research and scientific papers

Two Emissive Long-Lived Excited States of an Imidazole-Functionalized Ruthenium Dipyridophenazine Complex

A ruthenium(II) polypyridine-type complex based on the dipyridophenazine ligand with a directly fused imidazole unit (L1, dipyrido[3,2-a:2′,3′-c]phenazine-10,11-imidazole) has been synthesized, and its electrochemical and photophysical properties have been studied. The cyclic voltammogram of [Ru(tbbpy)2(L1)]2+ (C1) (tbbpy is 4,4′-tert-butyl-2,2′-bipyridine) shows a cathodic shift of the phenazine-based reduction process compared to similar molecules, while the first detected reduction wave (-1.34 V vs Fc/Fc+) is assigned to the imidazole unit within the molecule. On the basis of the TD-DFT calculations, the strong visible absorption band exhibited by C1 is assigned to a metal-to-ligand charge transfer (MLCT) transition with a concurrent ligand-centered (LC) transition. At room-temperature, C1 features emission (φ = 0.04) from its lowest excited states with time constants of 1.2 and 18.3 μs. These lifetimes are assigned to emission processes from the 3MLCT and 3LC state, respectively. This is the first time that a long-lived dual emission has been observed for a ruthenium(II) complex bearing a directly fused extended π-system. Furthermore, the emission of C1 is quenched upon water addition. In contrast to related compounds based on a dipyridophenazine ligand, the excited state energy is not shifted, and the lifetime is drastically decreased to 169 ns.

Molecular "light switch" for G-quadruplex DNA: Cycling the switch on and off

We report a new G-quadruplex DNA "light switch", where the light switch can be cycled on and off through the successive introduction of G-quadruplex DNA and [Fe(CN)6]4- ions.

NHC-Ir(I) complexes derived from 5,6-dinitrobenzimidazole. Synthesis, characterization and preliminary evaluation of their in vitro anticancer activity

The design, synthesis, characterization and in vitro anticancer activity of a series of Ir(I) NHC complexes derived from 5,6-dinitrobenzimidazole is reported. The evaluation was performed in five human cancer cell-lines, namely glioblastoma (U-251), prostatic adenocarcinoma (PC-3), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7) and lung adenocarcinoma (SKLU-7), including healthy cells of African green monkey kidney (COS-7) for comparative purposes. The complexes exhibited better activity in comparison with the corresponding NHC ligand precursors. In particular, complex (4a) exhibited a good performance against PC-3 and SKLU-1 with IC50 values of 10.6 ± 0.9 μM and 10.4 ± 1.5 μM, respectively.

The Forgotten Nitroaromatic Phosphines as Weakly Donating P-ligands: An N-Aryl-benzimidazolyl Series in RhCl(CO) Complexes

The coordination chemistry of a priori weakly σ-donating nitroaromatic phosphines is addressed through a series of nitro-substituted (N-phenyl-benzimidazol-1-yl)diphenylphosphines in RhI complexes. From a set of seven such phosphines L=Lxyz (′) (x, y, z=0 or 1=number of NO2 substituents at the 5, 6 and N-Ph para positions, respectively), including the non-nitrated parent L000 and its dicationic N-methyl counterpart L000′, three LRhCl(COD) and seven L2RhCl(CO) complexes have been obtained in 72–95 % yield. Despite of a cis orientation of the L and CO ligands, the C=O IR stretching frequency νCO varies in the expected sense, from 1967±1 cm?1 for Lxy0 to 1978±1 cm?1 for Lxy1, and 2005 cm?1 for L000′. The 103Rh NMR chemical shift δRh varies from ?288 ppm for L000 to ?316±1 ppm for L10z or L01z, and ?436 ppm for L000′. The νCO and δRh probes thus reveal moderate but systematic variations, and act as “orthogonal” spectroscopic indicators of the presence of nitro groups on the N-Ph group and the benzimidazole core, respectively. For the dicationic ligand L000′, a tight electrostatic sandwiching of the Rh-Cl bond by the benzimidazole moities is evidenced by X-ray crystallography (RhClδ????CN2 + ≈3.01 ?). Along with the LRhCl(CO) complexes, dinuclear side-products (μ-CO)(RhClL)2 were also obtained in low spectroscopic yield: for the dinitro ligand L=L011, a unique 1:6.7 clathrate structure, with dichloromethane as solvate, is also revealed by X-ray crystallography.

Reaction of substituted pyrido[1,2-a]benzimidazoles with electrophilic agents

The reactivity of substituted pyrido[1,2-a]benzimidazoles toward electrophilic aromatic substitution has been studied. An unusual introduction of an electrophilic species at the ortho position with respect to an electron-withdrawing group was found, and investigated. Changing the substituent nature from a meta director to an ortho/para director did not alter the selectivity of electrophilic substitution. Assignment of the proton and carbon spectra for the products of SEAr reactions were carried out using 1D and 2D NMR and the structures of selected nitro- and dinitropyrido[1,2-a]benzimidazoles were confirmed by single crystal X-ray diffraction.

A dibenz[a,c]phenazine-supported N-heterocyclic carbene and its rhodium and iridium complexes

A new polycyclic N-heterocyclic carbene featuring a fused dibenz[a,c]phenazine moiety was generated in situ from the corresponding tetrafluoroborate salt. The synthesis and NMR data of its corresponding precursors, its sulfur adduct and dimer are reported

BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

The present invention relates to benzimidazole derivatives and their pharmaceutical compositions and uses, specifically to benzimidazole derivatives of Formula (I), or their stereoisomer, pharmaceutically acceptable salt or solvates thereof, in which R1, R2, R3, R4, R5 and n have the definitions in the description; the present invention further relates to a pharmaceutical composition containing the compounds, methods for preparing the compounds, and use of the compounds for manufacturing of a medicament for prophylaxis and/or treatment of peptic ulcer, ulcer hemorrhage and diseases associated with gastric acid.