Author: Jessica.F

The author of 《Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903》 were Sharma, Swagat H.; Pablo, Juan Lorenzo; Montesinos, Monica Suarez; Greka, Anna; Hopkins, Corey R.. And the article was published in Bioorganic & Medicinal Chemistry Letters in 2019. Safety of 2-Chloro-1H-benzo[d]imidazole The author mentioned the following in the article:

The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biol. characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of I, a TRPC5 inhibitor that is active in multiple animal models of CKD. The results came from multiple reactions, including the reaction of 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Safety of 2-Chloro-1H-benzo[d]imidazole)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) is an analog of benzimidazole that has been synthesized by Langmuir adsorption isotherm. It is a white crystalline solid that can be dissolved in water and hydrochloric acid. 2-Chloro-1H-benzo[d]imidazole inhibits the growth of herpes simplex virus by acting as a competitive inhibitor for the viral enzyme thymidine kinase, which catalyzes the conversion of thymine to thymidine.Safety of 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Density, Refractive Index and Volumetric Properties of Water-Ionic Liquid Binary Systems with Imidazolium-Based Cations and Tetrafluoroborate, Triflate and Octylsulfate Anions at T = 293 to 343 K and p = 0.1 MPa》 were Carissimi, Guzman; Montalban, Mercedes G.; Diaz Banos, F. Guillermo; Villora, Gloria. And the article was published in Journal of Chemical & Engineering Data in 2019. Electric Literature of C8H15BF4N2 The author mentioned the following in the article:

The d. and refractive index of ionic liquids (ILs) + water binary mixtures were determined as a function of temperature (from 293.15 to 343.15 K) at atm. pressure over the whole composition range in which the mixtures were miscible. To carry out a systematic study, all of the ILs selected are imidazolium-based ILs with a different number of carbons in the alkyl chain of the cation and also different anions (tetrafluoroborate, triflate, and octylsulfate). Specifically, the studied ILs were 1-ethyl-3-methylimidazolium tetrafluoroborate [emim][BF4], 1-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF4], 1-hexyl-3-methylimidazolium tetrafluoroborate [hmim][BF4], 1-methyl-3-octylimidazolium tetrafluoroborate [omim][BF4], 1-ethyl-3-methylimidazolium triflate [emim][TfO], 1-butyl-3-methylimidazolium triflate [bmim][TfO], and 1-butyl-3-methylimidazolium octylsulfate [bmim][OcSO4]. The excess molar volumes and the deviation in the molar refraction of the binary mixtures were calculated for a better understanding of the interactions that take place between the components and were successfully correlated by the Redlich-Kister empirical correlations. The Bahe-Varela model, which has a more phys. meaning, was also used to successfully correlate the excess molar volume values. Volumetric properties, such as apparent molar volumes, partial molar volumes, isobaric thermal expansion coefficients, partial molar volumes at infinite dilution and excess partial molar volumes at infinite dilution were also calculated in order to obtain information about the influence of composition and temperature on the thermodn. behavior of the selected ILs and water in the mixture The results are discussed in order to understand the formation of hydrogen bonds between components of the mixture and the possible packing effects that take place in the mixing process. The d. and refractive index exptl. data were correlated by the Lorentz-Lorenz, Wiener, Dale-Gladstone, and Eykman equations to determine the relationship between both parameters, and good agreement between the exptl. and calculated refractive index values was obtained. The experimental part of the paper was very detailed, including the reaction process of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6Electric Literature of C8H15BF4N2)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. Actually, lonic liquids as innovative fluids have received wide attention only during the past two decades. The number of SCI papers published on lonic liquids has exponentially increased from a few in 1996 to >5000 in 2016, exceeding the annual growth rates of other popular scientific areas. Electric Literature of C8H15BF4N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Espiritu, Adrian I.; Remalante-Rayco, Patricia Pauline M. published their research in Multiple Sclerosis and Related Disorders in 2021. The article was titled 《High-dose biotin for multiple sclerosis: A systematic review and meta-analyses of randomized controlled trials》.Computed Properties of C10H16N2O3S The article contains the following contents:

Biotin may activate the acetyl-CoA-, 3-methylcrotonyl-CoA-, propionyl-CoA-, and pyruvate carboxylases to increase myelin repair and/or synthesis, and may enhance the production of ATP (ATP), which may be essential to prevent neurodegeneration. The purpose of this review was to determine the effectiveness and safety of high-dose biotin (HDB) in multiple sclerosis via a systematic review of randomized controlled trials. We searched the following electronic databases for relevant articles: MEDLINE, CENTRAL, EMBASE, Scopus, and ClinicalTrials.gov website until Apr. 2021. We considered randomized clin. trials (RCTs) that involved adult patients diagnosed with any phenotype of multiple sclerosis that conforms with the McDonald 2010/2017 criteria or the Lublin 2014 criteria. We included studies employing high-dose biotin or “”MD1003″” administered orally for at least 300 mg/day and given for at least three months. The methodol. quality assessment of the included studies was done using the Cochrane Risk of Bias (RoB) tool. The GRADE approach was used to assess the certainty of evidence [COE]. Out of 366 records identified, three RCTs involving 889 individuals diagnosed with MS (830 participants had progressive MS (PMS); 59 had RRMS) were pooled for analyses. The overall female:male ratio was 1.16:1. All included trials used HDB as an adjunctive treatment. The risks of bias in the three studies were low across the domains. At 12 to 15 mo, there is insufficient evidence that the HDB and placebo arms differed in terms of composite improvement of MS-related disability (relative risk (RR) 2.87; 95% CI 0.29-28.40; 2 trials; 796 participants; I2 = 66%) [low COE], improvement in expanded disability status scale (IEDSS) (RR 2.27; 95% CI 0.25-20.98; 2 trials; 796 participants; I2 = 63%) [low COE], and both IEDSS and improvement in 25-ft walk time (ITW25) (IEDSS-ITW25) (RR 0.58; 95% CI 0.17-2.00; 2 trials; 796 participants; I2 = 13%) [moderate COE] among patients with PMS. Pooled data for ITW25 at 12 to 15 mo yielded statistical significance (RR 2.06; 95% CI 1.04-4.09; 2 trials; 796 participants; I2 = 0%) [moderate COE] favoring HDB among patients with PMS. At 12 to 15 mo, no significant differences were found in terms of mean change in EDSS (MD -0.06; 95% CI -0.14-0.02; 2 studies; 796 participants; 889 participants; I2 = 68%) among patients with PMS. Synthesized data on incidence of any AEs (RR 0.98; 95% CI 0.92-1.04; 3 trials; I2 = 0%) [high COE] and any serious AEs (RR 0.98; 95% CI 0.77-1.24; 3 trials; 889 participants; I2 = 0%) [moderate COE] were not significantly different between HDB and placebo groups. Out of 662 pooled patients in the HDB group, 31 patients (4.7%) were found to have laboratory test interference compared to zero event in the pooled placebo group [high COE]. A moderate certainty of evidence suggests a potential benefit in favor of HDB administered for 12 to 15 mo in terms of ITW25 in patients with PMS. However, an important trade-off of this benefit is the high certainty of evidence suggesting an increased incidence of laboratory test interference when HDB is taken. After reading the article, we found that the author used 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5Computed Properties of C10H16N2O3S)

5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5) may be used to elute proteins from avidin/streptavidin resins. It has been used for culturing of oligodendrocytes.Computed Properties of C10H16N2O3S And it has been used for blocking endogenous biotin during immunohistology procedures.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Kattnig, B. Y. Mladenova; Chumakova, N. A.; Kattnig, D. R.; Grigor’ev, I. A.; Grampp, G.; Kokorin, A. I. published their research in Journal of Physical Chemistry B in 2021. The article was titled 《Influence of electric charge of spin probes on their diffusion in room-temperature ionic liquids》.Recommanded Product: 174501-65-6 The article contains the following contents:

The rotational and translational diffusion of neg. charged and uncharged spin probes in five imidazolium-based room-temperature ionic liquids (RTILs), 1-ethyl-3-methylimidazolium tetrafluoroborate, emimBF4, 1-butyl-3-methylimidazolium tetrafluoroborate, bmimBF4, 1-octyl-3-methylimidazolium tetrafluoroborate, omimBF4, 1-octyl-3-methylimidazolium hexafluorophosphate, omimPF6, and 1-octyl-3-methylimidazolium chloride, omimCl, has been studied by means of ESR spectroscopy. Detailed analyses of the spin-Hamiltonian parameters and spin exchange interactions have been carried out. The temperature dependences of the line broadening induced by the electronic dipole-dipole interaction and the electron spin exchange coupling are determined The translational mobility of spin probes is semiquant. characterized and successfully explained in the framework of a hypothesis based on the assumption of polar and unpolar domains within the RTILs. In the experiment, the researchers used 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6Recommanded Product: 174501-65-6)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. A multidisciplinary study on lonic liquids is emerging, including chemistry, materials science, chemical engineering, and environmental science. More specifically, some important fundamental viewpoints are now different from the original concepts, as insights into the nature of lonic liquids become deeper. For example, the physicochemical properties of lonic liquids are now recognized as ranging broadly from the oft quoted “nonvolatile, non-flammable, and air and water stable” to those that are distinctly volatile, flammable, and unstable. Recommanded Product: 174501-65-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《New expanded-ring NHC platinum(0) complexes: Synthesis, structure and highly efficient diboration of terminal alkenes》 was written by Rzhevskiy, Sergey A.; Topchiy, Maxim A.; Lyssenko, Konstantin A.; Philippova, Anna N.; Belaya, Maria A.; Ageshina, Alexandra A.; Bermeshev, Maxim V.; Nechaev, Mikhail S.; Asachenko, Andrey F.. Recommanded Product: 258278-25-0 And the article was included in Journal of Organometallic Chemistry on April 15 ,2020. The article conveys some information:

The synthesis and structural characterization of novel Pt(0) complexes are reported. A number of (NHC)Pt(dvtms) (dvtms = 1,3-divinyl-1,1,3,3-tetramethyldisiloxane) complexes were studied in catalytic addition of B2Pin2 to terminal alkenes. The novel expanded ring N-heterocyclic carbene complex (7-Dipp)Pt(dvtms) showed highest performance, turnover numbers up to 3800 were achieved. The scope of the reaction was illustrated by 20 examples with a variety of alkyl, alkoxy, halogen, ester, ketone and acetal substituents. In the experiment, the researchers used many compounds, for example, 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Recommanded Product: 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Recommanded Product: 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Synthesis and the reactions of 2,4,6-tris(ω-hydroxyalkyl)-1,3,5triazines》 was published in Bulletin of the Chemical Society of Japan in 1965. These research results belong to Nohira, Hiroyuki; Nishikawa, Yoshihiro; Furuya, Yoshiaki; Mukaiyama, Teruaki. Product Details of 2403-66-9 The article mentions the following:

From HO(CH2)nCN (I) and HCl were prepared the corresponding cyclic imino ethers HCl salts (II.HCl), which on treatment with Et3N gave the title compounds (III). The reactions of III with o-C6H4-(NH2)2 (IV) and 1,8-naphthalenediamine (V) were investigated. Treatment of Cl(CH2)3OH with KCN in EtOH-H2O (Aksnes and Prue, CA 53, 8004f) gave 30% I (n = 3), b11 1078°. A mixture of 22 g. Cl(CH2)4OH, 33 g. KCN, 50 ml. glycerol, and 25 ml. H2O heated and stirred 15 min. at 100-10°, cooled, and extracted with 4 50-ml. portions tetrahydrofuran (THF) gave 7.0 g. I (n = 4), b0.5 86-8°; when the distillation was carried out without extracting soon after the reaction was complete, almost 30% THF, b. 65-6° was formed as by-product. From Cl(CH2)5OH was similarly prepared 83% I (n = 5), b3 97-8°. Dry HCl passed into 300 ml. dry Et2O containing 8.5 g. I (n = 3) at 10-15° with cooling and the mixture let stand 2 days at room temperature in a stoppered flask gave 11.5 g. II (n = 3) HCl salt, m. 103-5°. Similar treatment of I (n = 4) with HCl but in more dilute (1.5-2.0%) Et2O solution gave 90% II (n = 4) HCl salt, m. 128-9°. Dry HCl passed into 150 ml. dry Et2O and 80 ml. dry glycol acetal-free dioxane containing 4.5 g. I (n = 5) with cooling and the mixture kept 4 days at room temperature, refluxed 3 hrs., and evaporated in vacuo gave 5.1 g. H (n = 5) HCl salt, m. 143-4°. Heating II.HCl 5 min. at 150-60° or refluxing them in PhMe gave the corresponding Cl(CH2)nCONH2 (VI). The following VI were prepared (n, % yield, and m.p. given): 3, 95, 97°; 4, 80, 78°; 5, 95, 102°. II.HCl (0.08 mole) and 16.0 g. Et3N in 80 ml. absolute THF let stand 3 days at room temperature in a stoppered flask with intermittent shaking and the solution filtered and fractionated gave the following III (n, % yield, and b.p./ mm. given): 3, 53, 196-8°/0.1; 4, 70, 207-9°/0.04; 5, 50, 21821°/0.01. III (n = 3) (0.5 g.) and 0.7 g. PhNCO in 10 ml. THF let stand 2 days and evaporated gave 1.1 g. VII, m. 124-5° (95% EtOH). III and 3 mol. equivalents IV or V heated at 220-30° (oil bath) under N evolution of NH3 ceased (15-60 min.) and the mixture cooled and washed with Et2O gave VIII and IX, resp. The following VIII and IX were prepared (n, % yield, and m.p. given): VIII: 3, 85, 160-1° (THF) (O-Ac derivative m. 88-9°); 4, 79, 1645° (THF) (O-Ac derivative m. 95-7°; O,N-di-Ac deriv, m. 68-9°); 5, 55, 106° (EtOAc) (O,N-di-Ac derivative m. 78-9°); IX: 3, 34, 145-6° (dioxane); 4, 45, 157-8° (THF); 5, 60, 185-7° (dioxane). The O-Ac derivatives of VIII were prepared by reaction of VIII and 1.2 mol. equivalents Ac2O in C2H5N at room temperature; the O,N-di-Ac derivatives of VIII were prepared by reaction of VIII and 2.5 mol. equivalents Ac2O in C5H5N at 100% III (n = 3) (0.5 g.) and 0.7 g. V heated 1 hr. at 250-60° (N atm.) and the mixture cooled and washed with Et2O gave 0.5 g. X, m. 143-4° (THF). Ir and uv data were given for III (n = 3, 4, and 5). The experimental part of the paper was very detailed, including the reaction process of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Product Details of 2403-66-9)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
Product Details of 2403-66-9 However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)On September 22, 2010 ,《C-C Coupling Reactivity of an Alkylgold(III) Fluoride Complex with Arylboronic Acids》 was published in Journal of the American Chemical Society. The article was written by Mankad, Neal P.; Toste, F. Dean. The article contains the following contents:

Previously, alkylgold(III) fluorides are proposed as catalytic intermediates that undergo C-C coupling with reagents such as arylboronic acids in Au(I)/Au(III) cross-coupling reactions. Here is reported the first exptl. evidence for this elementary mechanistic step. Complexes of the type (NHC)AuMe (NHC = N-heterocyclic carbene) were oxidized with XeF2 to yield cis-(NHC)AuMeF2 products, which are in equilibrium with their fluoride-dissociated, dimeric [(NHC)AuMe(μ-F)]2[F]2 forms. In one case, a monomeric cis-(NHC)AuMeF2 complex was favored exclusively in solution, and it reacts with a variety of ArB(OH)2 reagents to yield Ar-CH3 products. In the experimental materials used by the author, we found Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I))

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Agata, Ryosuke; Takaya, Hikaru; Matsuda, Hiroshi; Nakatani, Naoki; Takeuchi, Katsuhiko; Iwamoto, Takahiro; Hatakeyama, Takuji; Nakamura, Masaharu published an article on February 28 ,2019. The article was titled 《Iron-catalyzed cross coupling of aryl chlorides with alkyl grignard reagents: synthetic scope and Fe(II)/Fe(IV) mechanism supported by X-ray absorption spectroscopy and density functional theory calculations》, and you may find the article in Bulletin of the Chemical Society of Japan.Product Details of 258278-25-0 The information in the text is summarized as follows:

A combination of Fe(III) fluoride and 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr) catalyzes the high-yielding cross coupling of an electron-rich aryl chloride with an alkyl Grignard reagent, which cannot be attained using other Fe catalysts. A variety of alkoxy- or amino-substituted aryl chlorides can be cross-coupled with various alkyl Grignard reagents regardless of the presence or absence of β-hydrogens in the alkyl group. A radical probe experiment using 1-(but-3-enyl)-2-chlorobenzene does not afford the corresponding cyclization product, therefore excluding the intermediacy of radical species. Solution-phase x-ray absorption spectroscopy (XAS) anal., with the help of d. functional theory (DFT) calculations, indicates the formation of a high-spin (S = 2) heteroleptic difluorido organoferrate(II), [MgX][Fe(II)F2(SIPr)(Me/alkyl)], in the reaction mixture DFT calculations also support a feasible reaction pathway, including the formation of a difluorido organoferrate(II) intermediate which undergoes a novel Lewis acid-assisted oxidative addition to form a neutral organoiron(IV) intermediate, which leads to an Fe(II)/Fe(IV) catalytic cycle, where the fluorido ligand and the Mg ion play key roles. The results came from multiple reactions, including the reaction of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Product Details of 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Product Details of 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Wenzel, Anna G.; Grubbs, Robert H. published their research in Journal of the American Chemical Society on December 20 ,2006. The article was titled 《Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates》.HPLC of Formula: 866926-59-2 The article contains the following contents:

Ru(IV) metallacycles derived from both ethylene and propene are reported. The propene-derived metallacycles represent the 1st observed examples of substituted ruthenacyclobutanes and offer new insight into the preferred stereochem. orientation about metathesis intermediates. The authors showed evidence supporting the bottom-face orientation of Ru(IV) metallacycles derived from both ethylene and propene. The unsym. disubstituted 1-(2,6-diisopropylphenyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolinium chloride ([H2ImesiPrH]+Cl-) and the ruthenium carbene complex [(H2ImesiPr)Ru(:CHPCy3)(Cl)2]+[BF4]- were prepared The mol. structure of the ruthenium carbene complex was determined by x-ray crystallog. Reaction of the ruthenium carbene complex with ethylene gave a ruthenacyclobutane possessing an unsym. N-heterocyclic carbene (NHC) ligand. The complex was studied to ascertain the dynamics of the NHC relative to the metallacycle ring. Ruthenacyclobutanes studied possess exchange cross-peaks between the α- and β-positions in the 2-dimensional NMR, indicating a dynamic structure. The ruthenacyclobutanes derived from ethylene and propene proceed through nonproductive metallacycle formations/cycloreversions prior to olefin exchange. The implications of these results to the mechanism of Ru-catalyzed olefin metathesis are discussed. In the part of experimental materials, we found many familiar compounds, such as 1-(2,6-Diisopropylphenyl)-3-mesityl-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 866926-59-2HPLC of Formula: 866926-59-2)

1-(2,6-Diisopropylphenyl)-3-mesityl-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 866926-59-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.HPLC of Formula: 866926-59-2 Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 1923,King, Harold; Murch, Wm. O. published 《Bromination of glyoxaline-4-carboxanilide》.Journal of the Chemical Society, Transactions published the findings.SDS of cas: 16681-56-4 The information in the text is summarized as follows:

The object of this investigation was the preparation of 4-bromoglyoxaline-5-carboxylic acid (I) with the view of synthesizing xanthine by condensation of the ester with CO(NH2)2. The acid was obtained but the small yields have prevented attempts at the condensation. Two mols. Br react with glyoxaline-4-carboxanilide in glacial AcOH, giving a mixture of mono-, di- and tri-Br derivatives This is extracted with H2O on the boiling H2O bath. The aqueous solution deposits glyoxaline-4-carbox-p-bromoanilide, crystallizing from AcOH with 2 AcOH of crystallization, lost at 100° and then m. 273-4°. Hydrolysis gives I. 5-Bromoglyoxaline-4-carbox-p-bromoanilide (II), m. 245-6°, is then extracted with very dilute HCl. The residue is the 2,5-dibromo derivative (III), C10H6ON3Br3, which crystallines with 1 C2H4O2, and m. 257-8° (decomposition). Hydrolysis of III with HCl (sealed tube at 150° for 3 hrs.) gave p-BrC6H4NH2, and a mixture containing about 95% dichloro- and 5% dibromoglyoxaline, m. 184-5°. Hydrolysis of III with HBr gave a mixture of the 2,5-Br2 derivative and 2-bromoglyoxaline, m. 207°; Pauly’s reagent gives a deep orange color; picrate, yellow, m. 232° (decomposition); nitrate, decomposes violently 137°. 2,5-Dibromoglyoxaline nitrate-silver nitrate, 2C3H2N2Br2.AgNO3.HNO3. II is soluble in about 6 parts boiling AcOH. It is mixed with a very small amount of a compound containing about 50% Br and m. 247°. Hydrolysis of II with 24% HBr gives p-BrC6H4NH2 and 5-bromoglyoxaline-4-carboxylic acid, m. 265°, soluble in 50 parts boiling H2O, and forms a hydrochloride, nitrate, Ag salt, and gives a deep orange color with Pauly’s reagent. Et ester, m. 170-1°. With 30% HBr some 4-bromoglyoxaline was also isolated. Bromination of II gave III with some of the compound m. 247°. The results came from multiple reactions, including the reaction of 2-Bromo-1H-imidazole(cas: 16681-56-4SDS of cas: 16681-56-4)

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. SDS of cas: 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem