6745-43-3

Usage

Uses

Used in Pharmaceutical Industry:
IMidazole-d3 is used as a key component in the synthesis of biologically active compounds for the pharmaceutical industry. Its presence in the amino acid histidine and various antifungal medications highlights its importance in drug development and therapeutic applications.
Used in Chemical Industry:
IMidazole-d3 is used as a corrosion inhibitor for transition metals such as copper in the chemical industry. Its ability to prevent the degradation of these metals contributes to the longevity and performance of materials used in various industrial applications.

Upstream product

• 288-32-4 1H-imidazole 
• 6923-01-9 1,2,4,5-deuterated imidazole 

Downstream Products

• 53716-58-8 4,5-dideuterio-1H-imidazole 

Relevant academic research and scientific papers

CD38 INHIBITORS

One embodiment of the invention is a compound represented by Formula I: or a pharmaceutically acceptable salt thereof. The variables in Formula I are defined herein. Compounds of Formula I are CD38 inhibitors, which can be used to treat a disease or condition in a subject that benefits from an increase in NAD+ or to treat a mitochondrial disorder in a subject.

METHOD FOR DEUTERATION OR TRITIATION OF HETEROCYCLIC RING

The present invention relates to a method for deuteration of a heterocyclic ring, which comprises subjecting a compound having a heterocyclic ring to sealed refluxing state in a deuterated solvent in the presence of an activated catalyst selected form a palladium catalyst, a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst. In accordance with a method of the present invention, a hydrogen atom belonging to a heterocyclic ring of a compound having a heterocyclic ring can be very efficiently deuterated because temperature of deuteration reaction can be maintained at higher than boiling point of the solvent. Further, a method for deuteration of the present invention can be applied widely to deuteration of various compounds having a heterocyclic ring which are liable to decomposition under supercritical conditions or acidic conditions, leading to industrial and efficient deuteration of a compound having a heterocyclic ring.

Strong coupling effects in the polarized IR spectra of the chain hydrogen bond systems in imidazole crystals: H/D isotopic 'self-organization' effects in the IR spectra of isotopically diluted imidazole single crystals

This paper presents the investigation results of the polarized IR spectra of H1245 imidazole crystals and of D1H245, D1245 and H1D245 imidazole deuterium derivative crystals. The spectra were measured using polarized light at the room temperature and at 77 K by a transmission method, for two different crystalline faces. Theoretical analysis of the results concerned linear dichroic effects, H/D isotopic and temperature effects, observed in the spectra of the hydrogen and of the deuterium bonds in imidazole crystals, at the frequency ranges of νN-H and νN-D bands. The basic crystal spectral properties can be satisfactorily interpreted in a quantitative way for a hydrogen bond linear dimer model. Such a model explains not only a two-branch structure of the νN-H and νN-D bands in crystalline spectra, but also some essential linear dichroic effects in the band frequency ranges, for isotopically diluted crystals. Model calculations, performed within the limits of the strong-coupling model, allowed for quantitative interpretation and for understanding of the basic properties of the hydrogen bond IR spectra of imidazole crystals, H/D isotopic, temperature and dichroic effects included. The results allowed verification of theoretical models proposed recently for the imidazole crystal spectra generation mechanisms. In the scope of our studies, the mechanism of H/D isotopic self-organization processes, taking place in the crystal hydrogen bond lattices, was also recognized. It was proved that for isotopically diluted crystalline samples of imidazole, a non-random distribution of protons and deuterons exclusively occurs in some restricted fragments (domains) of open chains of the hydrogen-bonded molecules. Nevertheless, these co-operative interactions between the hydrogen bonds do not concern adjacent fragments of neighboring hydrogen bond chains in the lattice. Analysis of the isotopic self-organization effects in the spectra of imidazole crystals delivered crucial arguments for understanding of the nature of the hydrogen bond spectra generation mechanisms.

Solid-state deuterium nmr of imidazole ligands in cytochrome C peroxidase

We have measured hyperfine shifted NMR signals associated with deuterated imidazole bound to the high-spin Fe3+ state of cytochrome c peroxidase using deuterium magic angle spinning solid-state NMR. These experiments were performed on a mutant of cytochrome c peroxidase, CcP(H175G), for which replacement of the proximal histidine with glycine produced a cavity that can bind a variety of substituted imidazoles including imidazole or 2-methylimidazole. The mutant with imidazole bound is inactive; specifically its reaction with H2O2 is blocked. We observed deuterium NMR signals from the methyl-d3 group of the perdeuterated 2-MeIm sample bound to H175G CcP. The signal displayed an upfield chemical shift and exhibited non- Curie temperature dependence, indicating the existence of low-lying excited electronic states. Upon introducing a nondeuterated competitive ligand, imidazole, a decrease in the intensity of this signal was detected, consistent with the assignment of the deuterium signal to the bound 2- methylimidazole in the solid state. The tensor of the deuterium static line shape indicates the methyl group on the untethered imidazole ring undergoes rather unhindered motion while the entire ring has relatively limited motion. No evidence for intermediate ring flipping exchange dynamics nor for large angular librations of the ring is observed. This the absence of enzymatic activity in the mutant is unlikely to result from excessive dynamic disorder of the untethered imidazole.

Reactions of Coordinated Ligands. The Bromination of 2,4-Dimethyl-3H-imidazole and 3H-Imidazole Coordinated (at N 1) to Pentaamminecobalt(III)

The pH dependence of the bromination of R-2,4-Me2ImH3+ by Br2 in acidic aqueous solution, giving R-2,4-Me2-5-BrImH3+, suggests that proton abstraction from a bromine-substituted Wheland intermediate is rate determining for pH--catalysed and spontaneous paths are observed), while in the pH range 3-5, bromine addition is rate determining.For pH>5 the reaction may be interpreted to occur through rate-determining Br2 addition to the conjugate base from of the reactant.Rate constants for bromine addition to R-2,4-Me2ImH3+ and R-2,4-Me2Im2+are respectively 1.1*104 and 3.4*1010 dm3 mol-1 s-1 at 25.0 deg C, I=1.0 (NaClO4).Bromination of RImH3+, to give R-4-BrImH3+ initially, appears to occur largely via the conjugate base form of the reactant (k2=3.6*109 dm3 mol-1 s-1), but for pH3+ contributes to the observed rate (k1=0.68 dm3 mol-1 s-1).Ea=61+/-2 kJ mol-1 for the former process, and the primary kinetic isotope effect, kH/kD, increases from 1.3 in 0,05 M H+ to 2.4 in 5.42 M HClO4.These observations are discussed in terms of diffusion-controlled, or preassociation-type mechanisms.

Resonance Raman Spectra of Dioxygen Adducts of Cobalt Porphyrin-Imidazole Complexes. Remarkable Spectroscopic Consequences of Hydrogen Bonding of the Coordinated Imidazole and the Lack of an Effect on the Cobalt-Oxygen Linkage

Resonance Raman (RR) spectroscopic studies of O2 adducts of the imidazole complexes of a highly protected cobalt-porphyrin are reported.Strategic isotopic labeling studies, employing dioxygen isotopomers and selectively deuteriated imidazole analogues, are used to document and interpret the complicated spectral patterns that emerge as a result of complex vibrational coupling of ν(O-O) with internal modes of the trans-coordinated imidazole ligand.In addition, the observed spectral patterns are shown to be dependent upon temperature, imidazole concentration, and theaddition of a hydrogen-bond acceptor.These results indicate that hydrogen bonding of the ligated imidazole to other solution components does not lead to differences in the inherent frequency of ν(O-O) but does result in dramatic alterations of the observed spectral patterns as a consequence of diferences in vibrational coupling parameters.The implications of these studies for the interpretation of RR spectra of O2 adducts of cobalt-substituted hemeproteins are discused.