Author: Jessica.F

《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

Abe, Yoshito; Kayakiri, Hiroshi; Satoh, Shigeki; Inoue, Takayuki; Sawada, Yuki; Imai, Keisuke; Inamura, Noriaki; Asano, Masayuki; Hatori, Chie; Katayama, Akira; Oku, Teruo; Tanaka, Hirokazu published an article on February 12 ,1998. The article was titled 《A Novel Class of Orally Active Non-Peptide Bradykinin B2 Receptor Antagonists. 1. Construction of the Basic Framework》, and you may find the article in Journal of Medicinal Chemistry.Product Details of 79707-11-2 The information in the text is summarized as follows:

A novel class of potent, selective, and orally active non-peptide bradykinin (BK) B2 receptor antagonists were designed and synthesized starting from 8-benzyloxyimidazo[1,2-a]pyridine derivative(I). The unique screening lead I was discovered by a 2-step intentional random screening process, involving recognition of the relationship between BK and angiotensin II (Ang II) and the common structural features. Systematic chem. modification of I elucidated the structural requirements essential for B2 binding affinity leading to the identification of 8-[[3-(N-acylglycyl-N-methylamino)-2,6-dichlorobenzyl]oxy]-3-halo-2-methylimidazo[1,2-a]pyridine skeleton as the basic framework of this new series of B2 antagonists. A mol. modeling study suggested the key role of the N-methylanilide moiety at the 3-position of the 2,6-dichlorobenzene ring to allow these compounds to adopt the characteristic active conformation. The representative lead compounds inhibited the specific binding of [3H]BK to guinea pig ileum membrane preparations expressing B2 receptors, with nanomolar IC50s and also displayed in vivo functional antagonistic activities against BK-induced bronchoconstriction in guinea pigs at an oral dose of 1 mg/kg. Pharmacokinetic studies of the N-butylamide and Et urea moieties at the 3-position of the 2,6-dichlorobenzene in rats highlighted their excellent oral bioavailabilities, indicating that they represent the first orally active non-peptide B2 antagonists reported to date. In the experiment, the researchers used 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Product Details of 79707-11-2)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.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. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Product Details of 79707-11-2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 1977,Journal of Medicinal Chemistry included an article by Kohn, Harold; Kohn, Barbara A.; Steenberg, Marie L.; Buckley, Joseph P.. Application of 60546-77-2. The article was titled 《Syntheses and pharmacological activity of substituted imidazolidinethiones and thioimidazolines》. The information in the text is summarized as follows:

Five title compounds, prepared by S-alkylation or N-acetylation of the appropriate imidazolidinethiones, all decreased respiration and body temperature and produced ptosis in rats in gross observation studies. Thioimidazolines N-carbomethoxy- (I) [60546-77-2] and N-acetyl-2-methylthioimidazoline (II) [60546-75-0] were the most active central nervous system depressants and had the highest safety index. The isomeric imidazolidinethiones N-carbomethoxy- (III) [60546-78-3] and N-acetyl-N’-methylimidazolidinethione (IV) [60546-76-1] were much less effective and were much more toxic. NMR and ir spectra of the compounds are presented and discussed. The results came from multiple reactions, including the reaction of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2Application of 60546-77-2)

Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Application of 60546-77-2 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 2020,Organic & Biomolecular Chemistry included an article by Zhou, Kai; Bao, Ming; Huang, Jingjing; Kang, Zhenghui; Xu, Xinfang; Hu, Wenhao; Qian, Yu. Computed Properties of C10H10N2O2. The article was titled 《Iron-catalyzed [3+2]-cycloaddition of in situ generated N-ylides with alkynes or olefins: access to multi-substituted/polycyclic pyrrole derivatives》. The information in the text is summarized as follows:

An iron-catalyzed one-pot three-component reaction of 1-substituted benzimidazoles with diazoacetates and electron-deficient alkynes or alkenes has been reported. Mechanistically, the reaction goes through a 1,3-dipolar cycloaddition of catalytically generated benzimidazolium N-ylides with various activated alkynes or alkenes, leading to multi-substituted and polycyclic fused pyrrole derivatives, resp. In the part of experimental materials, we found many familiar compounds, such as Methyl 1-methyl-1H-benzo[d]Imidazole-6-carboxylate(cas: 131020-50-3Computed Properties of C10H10N2O2)

Methyl 1-methyl-1H-benzo[d]Imidazole-6-carboxylate(cas: 131020-50-3) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Computed Properties of C10H10N2O2 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

The author of 《Methanesulfonylation of 2-benzimidazolemethanol and α-(2-benzimidazolyl)benzyl alcohol》 were Charlson, Alexander J.. And the article was published in Carbohydrate Research in 1973. Computed Properties of C10H12N2O The author mentioned the following in the article:

Treatment of 2-benzimidazolemethanol (I) with MeSO2Cl and pyridine in CHCl3 afforded 2-(chloromethyl)-1-(methylsulfonyl)benzimidazole (II), which was also prepared by methylsulfonylation of 2-(chloromethyl)benzimidazole. Methylsulfonylation of α-(2-benzimidazolyl)benzyl alc. (III) in CHCl3 yielded 2-(α-chlorobenzyl)-1-(methylsulfonyl)benzimidazole. 1-(Methylsulfonyl)-2-benzimidazolemethanol was obtained on methylsulfonylation of I in pyridine at 0°, and α-[1-(methylsulfonyl)-2-benzimidazolyl]benzyl alc. (IV) was prepared from III by using the same reaction conditions. The reaction of 1-acetyl-2-(chloromethyl)benzimidazole with MeSO3Ag in benzene gave 1-acetyl-O-(methylsulfonyl)-2-benzimidazolemethanol. II has some antitumor activity in the KB cell-culture system, and some antibacterial activity in the Staphylococcus aureus test-system; it is also active in preventing anaphylactic shock in a mouse test-system.3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Computed Properties of 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.
However, the application of imidazoles is not limited to the field of peptides and peptidomimetics. Computed Properties of C10H12N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem