Category: imidazoles-derivatives

The author of 《Iridium-Catalyzed Enantioselective C(sp3)-H Amidation Controlled by Attractive Noncovalent Interactions》 were Wang, Hao; Park, Yoonsu; Bai, Ziqian; Chang, Sukbok; He, Gang; Chen, Gong. And the article was published in Journal of the American Chemical Society in 2019. Recommanded Product: 530-62-1 The author mentioned the following in the article:

While remarkable progress was made over the past decade, new design strategies for chiral catalysts in enantioselective C(sp3)-H functionalization reactions are still highly desirable. In particular, the ability to use attractive noncovalent interactions for rate acceleration and enantiocontrol would significantly expand the current arsenal for asym. metal catalysis. Herein, the authors report the development of a highly enantioselective Ir(III)-catalyzed intramol. C(sp3)-H amidation reaction of dioxazolone substrates for synthesis of optically enriched γ-lactams using a newly designed α-amino-acid-based chiral ligand. This Ir-catalyzed reaction proceeds with excellent efficiency and with outstanding enantioselectivity for both activated and unactivated alkyl C(sp3)-H bonds under very mild conditions. It offers the first general route for asym. synthesis of γ-alkyl γ-lactams. Water is a unique cosolvent to achieve excellent enantioselectivity for γ-aryl lactam production Mechanistic studies revealed that the ligands form a well-defined groove-type chiral pocket around the Ir center. The hydrophobic effect of this pocket allows facile stereocontrolled binding of substrates in polar or aqueous media. Instead of capitalizing on steric repulsions as in the conventional approaches, this new Ir catalyst operates through an unprecedented enantiocontrol mechanism for intramol. nitrenoid C-H insertion featuring multiple attractive noncovalent interactions. The results came from multiple reactions, including the reaction of Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Recommanded Product: 530-62-1)

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a peptide coupling reagent,it is used in the synthesis of peptides. Reacts readily with carboxylic acids to form acyl imidazoles; subsequent reaction with amines to form amides goes smoothly.Recommanded Product: 530-62-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Advanced Materials (Weinheim, Germany) included an article by Guo, Jiawei; Li, Dandan; Tao, Hui; Li, Gang; Liu, Renfeng; Dou, Yin; Jin, Taotao; Li, Lanlan; Huang, Jun; Hu, Houyuan; Zhang, Jianxiang. Recommanded Product: Di(1H-imidazol-1-yl)methanone. The article was titled 《Cyclodextrin-derived intrinsically bioactive nanoparticles for treatment of acute and chronic inflammatory diseases》. The information in the text is summarized as follows:

Inflammation is a common cause of many acute and chronic inflammatory diseases. A major limitation of existing anti-inflammatory therapeutics is that they cannot simultaneously regulate pro-inflammatory cytokine production, oxidative stress, and recruitment of neutrophils and macrophages. To overcome this limitation, nanoparticles (NPs) with multiple pharmacol. activities are synthesized, using a chem. modified cyclic oligosaccharide. The manufacture of this type of bioactive, saccharide material-based NPs (defined as LCD NP) is straight forward, cost-effective, and scalable. Functionally, LCD NP effectively inhibits inflammatory response, oxidative stress, and cell migration for both neutrophils and macrophages, two major players of inflammation. Therapeutically, LCD NP shows desirable efficacies for the treatment of acute and chronic inflammatory diseases in mouse models of peritonitis, acute lung injury, and atherosclerosis. Mechanistically, the therapeutic benefits of LCD NP are achieved by inhibiting neutrophil-mediated inflammatory macrophage recruitment and by preventing subsequent pro-inflammatory events. In addition, LCD NP shows good safety profile in a mouse model. Thus, LCD NP can serve as an effective anti-inflammatory nanotherapy for the treatment of inflammatory diseases mainly associated with neutrophil and macrophage infiltration. In addition to this study using Di(1H-imidazol-1-yl)methanone, there are many other studies that have used Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Recommanded Product: Di(1H-imidazol-1-yl)methanone) was used in this study.

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a peptide coupling reagent,it is used in the synthesis of peptides. Reacts readily with carboxylic acids to form acyl imidazoles; subsequent reaction with amines to form amides goes smoothly.Recommanded Product: Di(1H-imidazol-1-yl)methanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Safety of Di(1H-imidazol-1-yl)methanoneIn 2019 ,《A Pyrene-Poly(acrylic acid)-Polyrotaxane Supramolecular Binder Network for High-Performance Silicon Negative Electrodes》 appeared in Advanced Materials (Weinheim, Germany). The author of the article were Cho, Yunshik; Kim, Jaemin; Elabd, Ahmed; Choi, Sunghun; Park, Kiho; Kwon, Tae-woo; Lee, Jungmin; Char, Kookheon; Coskun, Ali; Choi, Jang Wook. The article conveys some information:

Although being incorporated in com. lithium-ion batteries for a while, the weight portion of silicon monoxide (SiOx, x ≈ 1) is only < 10 wt% due to the insufficient cycle life. Along this line, polymeric binders that can assist in maintaining the mech. integrity and interfacial stability of SiOx electrodes are desired to realize higher contents of SiOx. Herein, a pyrene-poly(acrylic acid) (PAA)-polyrotaxane (PR) supramol. network is reported as a polymeric binder for SiOx with 100 wt%. The noncovalent functionalization of a carbon coating layer on the SiOx is achieved by using a hydroxylated pyrene derivative via the π-π stacking interaction, which simultaneously enables hydrogen bonding interactions with the PR-PAA network through its hydroxyl moiety. Moreover, the PR's ring sliding while being crosslinked to PAA endows a high elasticity to the entire polymer network, effectively buffering the volume expansion of SiOx and largely mitigating the electrode swelling. Based on these extraordinary physicochem. properties of the pyrene-PAA-PR supramol. binder, the robust cycling of SiOx electrodes is demonstrated at com. levels of areal loading in both half-cell and full-cell configurations. After reading the article, we found that the author used Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Safety of Di(1H-imidazol-1-yl)methanone)

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a coupling agent in the synthesis of dipolar polyamides for nonlinear optical applications and polypeptides. It also used to make β-keto sulfones and sulfoxides, lead sequestering agents, and β-enamino acid derivatives.Safety of Di(1H-imidazol-1-yl)methanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Computed Properties of C3H5N3In 2020 ,《Proton-Induced Charge Transfer on Imidazole and 2-Aminoimidazole. Role of the Substituent and Influence of Stepwise Hydration》 appeared in Journal of Physical Chemistry A. The author of the article were Kerkeni, Boutheina; Bacchus-Montabonel, Marie-Christine. The article conveys some information:

The behavior of potential prebiotic species in space is of main concern in the chem. at the origin of life. Their reactivity or stability in spatial conditions, under strong UV radiations or ion bombardments, remains an open question and needs wide investigations. As protons are by far the most abundant ions in space, we focus presently on proton-induced collisions on imidazole and 2-aminoimidazole evidenced as important prebiotic RNA intermediates. Unconstrained full optimization of the structures was performed with B3LYP/cc-pVTZ model chem. The calculations were performed in a wide collision energy range in order to model various astrophys. environments, from eV in the interstellar medium, up to keV for solar winds or supernovae shock-wave protons. Such a study provides for the first time a theor. insight on the influence of the amino substituent on the proton-induced charge transfer. We evaluated the role of icy grain environments through a cluster approach modeling the effect of a stepwise microhydration on the process. Comparisons with oxygenated and sulfurated analogs address further qual. trends on the resp. stability or reactivity of such heterocycles which may be of tremendous interest in prebiotic chem. Charge transfer appears to be quite efficient for imidazole compounds and their sulfurated analog compared to the oxygenated heterocycle. The experimental process involved the reaction of 1H-Imidazol-2-amine(cas: 7720-39-0Computed Properties of C3H5N3)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Computed Properties of C3H5N3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Jacobi, Richard; Joerg, Florian; Steinhauser, Othmar; Schroeder, Christian published an article in Physical Chemistry Chemical Physics. The title of the article was 《Emulating proton transfer reactions in the pseudo-protic ionic liquid 1-methylimidazolium acetate》.Product Details of 616-47-7 The author mentioned the following in the article:

Proton transfer reactions can enhance conductivity in protic ionic liquids However, several proton reactions are possible in a multicomponent system of charged and neutral species, resulting in a complex reaction network. Probabilities and equilibrium concentrations of the involved species are modeled by the combination of reducible Markov chains and quantum-mech. calculations The experimental part of the paper was very detailed, including the reaction process of 1-Methyl-1H-imidazole(cas: 616-47-7Product Details of 616-47-7)

1-Methyl-1H-imidazole(cas: 616-47-7) is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate.Product Details of 616-47-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Bottari, Cettina; Almasy, Laszlo; Rossi, Barbara; Bracco, Brenda; Paolantoni, Marco; Mele, Andrea published an article in Journal of Physical Chemistry B. The title of the article was 《Interfacial Water and Microheterogeneity in Aqueous Solutions of Ionic Liquids》.SDS of cas: 174501-65-6 The author mentioned the following in the article:

In this work, aqueous solutions of two prototypical ionic liquids (ILs), [BMIM][BF4] and [BMIM][TfO], were investigated by UV Raman spectroscopy and small-angle neutron scattering (SANS) in the water-rich domain, where strong heterogeneities at mesoscopic length scales (microheterogeneity) were expected. Analyzing Raman data by a differential method, the solute-correlated (SC) spectrum was extracted from the OH stretching profiles, emphasizing specific hydration features of the anions. SC-UV Raman spectra pointed out the mol. structuring of the interfacial water in these microheterogeneous IL/water mixtures, in which IL aggregates coexist with bulk water domains. The organization of the interfacial water differs for the [BMIM][BF4] and [BMIM][TfO] solutions, being affected by specific anion-water interactions. In particular, in the case of [BMIM][BF4], which forms weaker H-bonds with water, the aggregation properties clearly depend on concentration, as reflected by local changes in the interfacial water. On the other hand, stronger water-anion hydrogen bonds and more persistent hydration layers were observed for [BMIM][TfO], which likely prevent changes in IL aggregates. The modeling of SANS profiles, extended to [BPy][BF4] and [BPy][TfO], evidences the occurrence of significant concentration fluctuations for all of the systems: this appears as a rather general phenomenon that can be ascribed to the presence of IL aggregation, mainly induced by (cation-driven) hydrophobic interactions. Nevertheless, larger concentration fluctuations were observed for [BMIM][BF4], suggesting that anion-water interactions are relevant in modulating the microheterogeneity of the mixture In the experiment, the researchers used 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6SDS of cas: 174501-65-6)

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. SDS of cas: 174501-65-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Steuer, Lena; Kaifer, Elisabeth; Himmel, Hans-Jorg published an article in European Journal of Organic Chemistry. The title of the article was 《Redox-Active Dendrimer-Like Oligoguanidines and Their Use in a Proton-Coupled Electron Transfer Reaction》.Reference of 2-Chloro-1H-benzo[d]imidazole The author mentioned the following in the article:

Redox-active organic dendrimers are of interest for a variety of applications, e. g. as components in optoelectronic devices and energy-storage (battery) materials, and were also used to model enzymic reactivity. Here, we report the first synthesis of redox-active dendrimer-like oligoguanidines, assembling six or twelve guanidino groups attached to aromatic cores in one mol. The novel oligoguanidines, being strong electron donors, are characterized in their stable (neutral and dicationic) redox states. Redox processes occur preferentially at the core, while the periphery provides highly Broensted basic sites. The combined electron and proton acceptor properties of the mols. in their stable oxidized dicationic redox state motivate applications in proton-coupled electron transfer (PCET) processes. In this work, we test their application in a representative intramol. oxidative aryl-aryl coupling reaction. The experimental process involved the reaction of 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Reference of 2-Chloro-1H-benzo[d]imidazole)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.Reference of 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Saeedian Moghadam, Ebrahim; Al-Saadi, Abdullah Mohammed; Talebi, Meysam; Amanlou, Massoud; Amini, Mohsen; Abdel-Jalil, Raid published an article in Synthetic Communications. The title of the article was 《Design, synthesis, and bioactivity investigation of novel benzimidazole derivatives as potent urease inhibitors》.Product Details of 934-32-7 The author mentioned the following in the article:

Herein, we synthesized a series of novel benzimidazole derivatives and screened their bioactivity as potent urease inhibitors. The structure of the was elucidated using spectroscopic technics (1H-NMR, 13C-NMR, MS), elemental anal., and m.p. The urease inhibition activity was evaluated using the urease enzyme inhibition kit. All , except , showed higher urease inhibition activity (0.77 to 6.25 μM) in comparison to thiourea and hydroxyurea as standard (IC50: 22 and 100 μM resp.). and exhibited the best activity with the IC50 value of 0.77 and 1.26 μM resp. A mol. docking study showed the mode of interactions between the most active compound and enzyme active site. To investigate the cytotoxicity profile of the target compounds, an MTT assay was done on two different cell lines which showed all have IC50 values higher than 50 μM on both tested cell lines.1H-Benzo[d]imidazol-2-amine(cas: 934-32-7Product Details of 934-32-7) was used in this study.

1H-Benzo[d]imidazol-2-amine(cas: 934-32-7) can be used in the hydrolysis of a choline carbonate. It was also used in the synthesis of imidazo[1,2-a]benzimidazoles.Product Details of 934-32-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Shen, Hui; Ge, Yiran; Wang, Junwei; Li, Hui; Xu, Yungen; Zhu, Qihua published their research in Bioorganic & Medicinal Chemistry Letters in 2021. The article was titled 《Design, synthesis and biological evaluation of novel molecules as potent PARP-1 inhibitors》.Recommanded Product: 2-Chloro-1H-benzo[d]imidazole The article contains the following contents:

Two series of novel compounds with pthalazin-1(2H)-one moiety such as I [X = N, CH; Y = C(O), CH2; Z = N, CH; R = H, OMe, OEt; R1 = H, C(O)NH2] and 4-(4-fluoro-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-2-carbonyl)benzyl)phthalazin-1(2H)-one II [R = H, 7-Me, 7-F, 7-Cl] with inhibition activity against PARP-1 were designed and synthesized. All target compounds I and II were evaluated for their PARP-1 inhibition activity and compounds with high PARP-1 inhibition activity were selected to assess for cellular assays in vitro. Among the synthesized compounds compound II [R = 7-F] displayed impressive results in both PARP-1 enzyme inhibition with IC50 value of 0.51 nM and anti-proliferation activity against HCT116 and HCC1937 cell lines with IC50 values of 6.62 nM and 12.65 nM, resp. Also, compound II [R = 7-F] exhibited good metabolic stability in vitro with t1/2 of 173.25 min and CLint of 0.04 mL/min/mg.. Prediction of mol. properties and protein docking were applied to structure design. Prediction of mol. properties and protein docking of compound II [R = 7-F] were applied to structure design. This study provided potential lead compounds and designed the directions for the development of PARP-1 inhibitors. After reading the article, we found that the author used 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Recommanded Product: 2-Chloro-1H-benzo[d]imidazole)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.Recommanded Product: 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles》 was written by Ni, Zhibin; Mou, Chengli; Zhu, Xun; Qi, Puying; Yang, Song; Chi, Yonggui Robin; Jin, Zhichao. Quality Control of 1,3-Dimesityl-1H-imidazol-3-ium chloride And the article was included in European Journal of Organic Chemistry in 2020. The article conveys some information:

A carbene-catalyzed oxidative cycloaddition reaction is developed for efficient access to multi-functionalized 2-phenylbenzothiazoles. A broad scope of heavily substituted arenes bearing 2-benzothiazole groups were prepared in good to excellent yields. The remote C(sp2)-H bond in the substituted arene products can be activated by Pd catalysts in regio-selective fashion with the direction of the 2-benzothiazole groups. In the experiment, the researchers used many compounds, for example, 1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Quality Control of 1,3-Dimesityl-1H-imidazol-3-ium chloride)

1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8) is a ligand for arylation of aldehydes and for carbene catalyzed intermolecular arylation of C-H bonds. It is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases.Quality Control of 1,3-Dimesityl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem