Month: October 2022

Ma, Zonghui; Jiang, Ling; Li, Bingyan; Liang, Dailin; Feng, Yu; Liu, Li; Jiang, Cheng published an article in 2021. The article was titled 《Discovery of benzimidazole derivatives as potent and selective aldehyde dehydrogenase 1A1 (ALDH1A1) inhibitors with glucose consumption improving activity》, and you may find the article in Bioorganic & Medicinal Chemistry.HPLC of Formula: 4857-06-1 The information in the text is summarized as follows:

Aldehyde dehydrogenase 1A1 (ALDH1A1) plays vital physiol. and toxicol. functions in many areas, such as CNS, inflammation, metabolic disorders, and cancers. Overexpression of ALDH1A1 has been disclosed to play an important role in obesity, diabetes and other diseases, indicating the potential need for the identification and development of small mol. ALDH1A1 inhibitors. Herein, a series of benzimidazole derivatives was designed, synthesized and evaluated. Among them, compounds 21, 27, 29, 61 and 65 exhibited excellent inhibitory activity against ALDH1A1 with IC50 values in the low micromolar range and high selectivity over ALDH1A2, ALDH1A3, ALDH2 and ALDH3A1. Moreover, an in vitro study demonstrated that all five compounds effectively improved glucose consumption in HepG2 cells, of which, 61 and 65 at 10 μM produced nearly equal glucose consumption with pos. control Metformin (Met) at 1 mM. Furthermore, 61 and 65 showed desirable metabolic stability in human liver microsomes. All these results suggest that 61 and 65 are suitable for further studies. In the experiment, the researchers used 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1HPLC of Formula: 4857-06-1)

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.HPLC of Formula: 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Hokmabadi, Fahimeh; Zadmard, Reza; Akbarzadeh, Ali; Tafakori, Vida; Jalali, Mohammad Reza; Ahmadian, Gholamreza published an article in Royal Society Open Science. The title of the article was 《Synthesis of a new chitosan-p-tert-butylcalix[4]arene polymer as adsorbent for toxic mercury ion》.COA of Formula: C7H6N4O The author mentioned the following in the article:

In this paper, we have synthesized a novel chitosan-p-tert-butylcalix[4]arene polymer (CCP) as a highly efficient adsorbent for mercury ion (Hg2+) removal from water. In fact, a lower rim diamine derivative of p-tert-butylcalix[4]arene has been cross-linked with chitosan chain by carbonyl diimidazole (CDI) as the linker. CDI forms a urea linkage between calix[4]arene diamine derivative and amine groups of the chitosan polymeric chain. The structure and properties of the new polymer were characterized by Fourier transform IR spectroscopy, X-ray diffraction and scanning electron microscope. Also, the adsorption capacity of CCP was studied towards Hg2+ in aqueous medium by inductively coupled plasma-optical emission spectrometry. Interestingly, the results showed a considerable adsorption capacity for CCP in comparison with chitosan. Therefore, CCP can be introduced as a promising adsorbent for the elimination of Hg2+ from wastewaters. Moreover, because of the conformity of adsorption kinetic with pseudo-second-order kinetic models, it can be concluded that chem. adsorption has an important role between functional groups on CCP polymer and Hg2+ ions. In addition, according to Freundlich isotherm, the CCP surface was heterogeneous with different functional groups. The experimental part of the paper was very detailed, including the reaction process of Di(1H-imidazol-1-yl)methanone(cas: 530-62-1COA of Formula: C7H6N4O)

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.COA of Formula: C7H6N4O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Product Details of 530-62-1In 2022 ,《Prebiotically Plausible Autocatalytic Peptide Amyloids》 appeared in Chemistry – A European Journal. The author of the article were Rout, Saroj K.; Rhyner, David; Riek, Roland; Greenwald, Jason. The article conveys some information:

The prebiotic emergence of mols. capable both of self-replication and of storing information was a defining event at the dawn of life. Still, no plausible prebiotic self-replication of biol. relevant mols. has been demonstrated. Building upon the known templating nature of amyloids, we present two systems in which the products of a peptide-bond-forming reaction act as self-replicators to enhance the yield and stereoselectivity of their formation. This first report of an amino acid condensation that can undergo autocatalysis further supports the potential role of amyloids in prebiotic mol. evolution as an environment-responsive and information-coding system capable of self-replication. The experimental process involved the reaction of Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Product Details of 530-62-1)

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.Product Details of 530-62-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application In Synthesis of 2-Chloro-1H-benzo[d]imidazoleIn 2018 ,《Molecular modeling, synthesis, antibacterial and cytotoxicity evaluation of sulfonamide derivatives of benzimidazole, indazole, benzothiazole and thiazole》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Naaz, Farha; Srivastava, Ritika; Singh, Anuradha; Singh, Nidhi; Verma, Rajesh; Singh, Vishal K.; Singh, Ramendra K.. The article conveys some information:

A new series of heterocyclic mols. bearing sulfonamide linkage has been synthesized and screened for antibacterial activity. During antibacterial screening using broth dilution method, mols. were found to be highly active (MIC value 50-3.1 μg/mL) against different human pathogens, namely B. cereus, S. aureus, E. coli and P. aeruginosa, and most effective against E. coli. A great synergistic effect was observed during determination of FIC where mols. were used in combination with reference drugs chloramphenicol and sulfamethoxazole. The MIC value of the combination – varying concentration of test compounds and 1/2 MIC of reference drugs or varying concentration of reference drugs and 1/2 MIC of test compounds, was reduced up to 1/4 or 1/32 of the original value, indicating thereby the combination was 4-32 times more potent than the test mol. The mols. also showed low degree of cytotoxicity against PBM, CEM and VERO cell lines. The results pos. indicated towards the development of lead antibacterials using the combination approach. In the experimental materials used by the author, we found 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Application In Synthesis 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.Application In Synthesis of 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Efficient synthesis of mibefradil analogues: an insight into in vitro stability》 was published in Organic & Biomolecular Chemistry in 2014. These research results belong to Lee, Ji Eun; Kwon, Tae Hui; Gu, Su Jin; Lee, Duck-Hyung; Kim, B. Moon; Lee, Jae Yeol; Lee, Jae Kyun; Seo, Seon Hee; Pae, Ae Nim; Keum, Gyochang; Cho, Yong Seo; Min, Sun-Joon. Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol The article mentions the following:

This article describes the synthesis and biol. evaluation of a chem. library of mibefradil analogs to investigate the effect of structural modification on in vitro stability. The construction of the dihydrobenzopyran structure in mibefradil derivatives I (X = CH2, O; R1 = H, Me, F, NO2, Cl, 5,6-(Cl)2, Br; R2 = H, iPr, CF3CH2, cyclopropyl) was achieved through two efficient approaches based on a diastereoselective intermol. Reformatsky reaction and an intramol. carbonyl-ene cyclization. In particular, the second strategy through the intramol. carbonyl-ene reaction led to the formation of a key intermediate II in a short and highly stereoselective way, which has allowed for practical and convenient preparation of analogs I. Using this protocol, we could obtain 22 new mibefradil analogs, which were biol. tested for in vitro efficacies against T-type calcium channels and metabolic stabilities. Among the synthesized compounds, we found that analog I (X = CH2, R1 = R2 = H) containing a dihydrobenzopyran ring and a secondary amine linker showed high % remaining activities of the tested CYP enzymes retaining the excellent T-type calcium channel blocking activity. These findings indicated that the structural modification of mibefradil was effective for improving in vitro stability, i.e., reducing CYP inhibition and metabolic degradation The experimental process involved the reaction of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol)

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.
However, the application of imidazoles is not limited to the field of peptides and peptidomimetics. Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Functionalized ZIF-7/Pebax 2533 mixed matrix membranes for CO2/N2 separation》 was written by Gao, Jie; Mao, Haizhuo; Jin, Hua; Chen, Chen; Feldhoff, Armin; Li, Yanshuo. Category: imidazoles-derivativesThis research focused onzeolite mixed matrix membrane carbon dioxide nitrogen separation. The article conveys some information:

Membrane-based separation technol. has evolved as a competitive approach for CO2 capture from flue gas (mainly N2). To achieve high separation performance, three partially NH2-, OH- and CH3OH- functionalized mixed-linker-ZIF-7 were successfully synthesized, and incorporated into polyether-block-amide (Pebax 2533) polymer to form mixed-matrix membranes (MMMs). As evidenced by the CO2 adsorption isotherms, introducing functional groups in the ZIF-7 framework was indeed beneficial for CO2 adsorption. All MMMs composed of ZIF-7-NH2, ZIF-7-OH and ZIF-7-CH3OH offered better CO2/N2 separation performance than the parent ZIF-7-Pebax 2533 membrane, suggesting the pos. effect of functionalized ZIF-7 fillers on the gas separation performance. Among the three functionalized ZIF-7 based MMMs, the ZIF-7-OH-Pebax MMMs exhibited the best performance for CO2/N2 separation, which might be ascribed to the highest adsorption selectivity of CO2 over N2 predicted by ideal adsorbed solution theory (IAST) for ZIF-7-OH fillers. The 14% ZIF-7-OH-Pebax MMM showed high CO2 permeability of 273 Barrer and CO2/N2 separation factor of 38, which increased by 60% and 145% as compared with the neat Pebax membrane. The strategy of preparing functionalized MOFs with strong affinity for CO2 provides an effective method to develop MMMs for highly efficient CO2 separation In the experiment, the researchers used 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7Category: imidazoles-derivatives)

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.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Identification and optimization of 2-aminobenzimidazole derivatives as novel inhibitors of TRPC4 and TRPC5 channels》 was published in British Journal of Pharmacology in 2015. These research results belong to Zhu, Yingmin; Lu, Yungang; Qu, Chunrong; Miller, Melissa; Tian, Jinbin; Thakur, Dhananjay P.; Zhu, Jinmei; Deng, Zixin; Hu, Xianming; Wu, Meng; McManus, Owen B.; Li, Min; Hong, Xuechuan; Zhu, Michael X.; Luo, Huai-Rong. COA of Formula: C10H12N2O The article mentions the following:

Background and Purpose : Transient receptor potential canonical (TRPC) channels play important roles in a broad array of physiol. functions and are involved in various diseases. However, due to a lack of potent subtype-specific inhibitors the exact roles of TRPC channels in physiol. and pathophysiol. conditions have not been elucidated. Exptl. Approach : Using fluorescence membrane potential and Ca2+ assays and electrophysiol. recordings, we characterized new 2-aminobenzimidazole-based small mol. inhibitors of TRPC4 and TRPC5 channels identified from cell-based fluorescence high-throughput screening. Key Results : The original compound, M084, was a potent inhibitor of both TRPC4 and TRPC5, but was also a weak inhibitor of TRPC3. Structural modifications of the lead compound resulted in the identification of analogs with improved potency and selectivity for TRPC4 and TRPC5 channels. The aminobenzimidazole derivatives rapidly inhibited the TRPC4- and TRPC5-mediated currents when applied from the extracellular side and this inhibition was independent of the mode of activation of these channels. The compounds effectively blocked the plateau potential mediated by TRPC4-containing channels in mouse lateral septal neurons, but did not affect the activity of heterologously expressed TRPA1, TRPM8, TRPV1 or TRPV3 channels or that of the native voltage-gated Na+, K+ and Ca2+ channels in dissociated neurons. Conclusions and Implications : The TRPC4/C5-selective inhibitors developed here represent novel and useful pharmaceutical tools for investigation of physiol. and pathophysiol. functions of TRPC4/C5 channels.3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9COA of Formula: C10H12N2O) was used in this study.

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.
COA of Formula: C10H12N2O However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Nickel-Catalyzed Intramolecular Desulfitative C-N Coupling: A Synthesis of Aromatic Amines》 was written by Liu, Jiangjun; Jia, Xiuwen; Chen, Xuemeng; Sun, Haotian; Li, Yue; Kramer, Soeren; Lian, Zhong. Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride And the article was included in Journal of Organic Chemistry on April 17 ,2020. The article conveys some information:

A nickel-catalyzed intramol. C-N coupling reaction via SO2 extrusion was presented. The use of a catalytic amount of BPh3 allowed the transformation to take place under much milder conditions (60°C) than previously reported C-N coupling reactions by CO or CO2 extrusion (160-180°C). In addition, this method displayed good functional group tolerance and versatility, as it can be applied to the synthesis of dialkyl aryl amines, alkyl diaryl amines and triaryl amines. The robustness of the desulfitative C-N coupling was demonstrated by three high-yielding gram-scale reactions. In the experiment, the researchers used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride)

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.Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Product Details of 258278-25-0On September 13, 2021 ,《Synthesis of L-Au(I)-CF2H Complexes and Their Application as Transmetalation Shuttles to the Difluoromethylation of Aryl Iodides》 was published in Organometallics. The article was written by Garcia-Dominguez, Patricia. The article contains the following contents:

We describe herein two alternative protocols to efficiently prepare difluoromethylgold(I) complexes bearing ancillary ligands with different electronic and steric properties. LAu-OX (X = H and t-Bu) species, formed in the presence of base, have been identified as intermediate complexes involved in these transformations. The application of these compounds as “”CF2H transmetalation shuttles”” from gold to palladium has been demonstrated in a Pd-catalyzed difluoromethylation reaction of aryl iodides, in which the Au-to-Pd transfer of “”CF2H”” is feasible under stoichiometric conditions. These findings will pave the way for catalytic manifolds in gold chem. The experimental part of the paper was very detailed, including the reaction process 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) 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.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

Application In Synthesis of Imidazo[1,2-a]pyridine-5-carbaldehydeOn September 20, 2007 ,《Inhibitors of Tumor Progression Loci-2 (Tpl2) Kinase and Tumor Necrosis Factor α (TNF-α) Production: Selectivity and in Vivo Antiinflammatory Activity of Novel 8-Substituted-4-anilino-6-aminoquinoline-3-carbonitriles》 was published in Journal of Medicinal Chemistry. The article was written by Green, Neal; Hu, Yonghan; Janz, Kristin; Li, Huan-Qiu; Kaila, Neelu; Guler, Satenig; Thomason, Jennifer; Joseph-McCarthy, Diane; Tam, Steve Y.; Hotchandani, Rajeev; Wu, Junjun; Huang, Adrian; Wang, Qin; Leung, Louis; Pelker, Jefferey; Marusic, Suzana; Hsu, Sang; Telliez, Jean-Baptiste; Hall, J. Perry; Cuozzo, John W.; Lin, Lih-Ling. The article contains the following contents:

Tumor progression loci-2 (Tpl2) (Cot/MAP3K8) is a serine/threonine kinase in the MAP3K family directly upstream of MEK. Recent studies using Tpl2 knockout mice have indicated an important role for Tpl2 in the lipopolysaccharide (LPS) induced production of tumor necrosis factor α (TNF-α) and other proinflammatory cytokines involved in diseases such as rheumatoid arthritis. Initial 4-anilino-6-aminoquinoline-3-carbonitrile leads showed poor selectivity for Tpl2 over epidermal growth factor receptor (EGFR) kinase. Using mol. modeling and crystallog. data of the EGFR kinase domain with and without an EGFR kinase-specific 4-anilinoquinazoline inhibitor (erlotinib, Tarceva), the authors hypothesized that the authors could diminish the inhibition of EGFR kinase by substitution at the C-8 position of the 4-anilino-6-aminoquinoline-3-carbonitrile leads. The 8-substituted-4-anilino-6-aminoquinoline-3-carbonitriles were prepared from the appropriate 2-substituted 4-nitroanilines. Modifications to the C-6 and C-8 positions led to the identification of compounds with increased inhibition of TNF-α release from LPS-stimulated rat and human blood, and these analogs were also highly selective for Tpl2 kinase over EGFR kinase. Further structure-activity based modifications led to the identification of 8-bromo-4-(3-chloro-4-fluorophenylamino)-6-[(1-methyl-1H-imidazol-4-yl)methylamino]quinoline-3-carbonitrile, which demonstrated in vitro as well as in vivo efficacy in inhibition of LPS-induced TNF-α production The experimental part of the paper was very detailed, including the reaction process of Imidazo[1,2-a]pyridine-5-carbaldehyde(cas: 372147-50-7Application In Synthesis of Imidazo[1,2-a]pyridine-5-carbaldehyde)

Imidazo[1,2-a]pyridine-5-carbaldehyde(cas: 372147-50-7) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Application In Synthesis of Imidazo[1,2-a]pyridine-5-carbaldehyde 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