Category: imidazoles-derivatives

《Heteroarylamide smoothened inhibitors: Discovery of N-[2,4-dimethyl-5-(1-methylimidazol-4-yl)phenyl]-4-(2-pyridylmethoxy)benzamide (AZD8542) and N-[5-(1H-imidazol-2-yl)-2,4-dimethyl-phenyl]-4-(2- pyridylmethoxy)benzamide (AZD7254)》 was published in Bioorganic & Medicinal Chemistry in 2020. These research results belong to Yang, Bin; Hird, Alexander W.; Bodnarchuk, Michael S.; Zheng, Xiaolan; Dakin, Les; Su, Qibin; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Brassil, Patrick; Redmond, Sean; John Russell, Daniel; Janetka, James W.. Category: imidazoles-derivatives The article mentions the following:

Aberrant hedgehog (Hh) pathway signaling is implicated in multiple cancer types and targeting the Smoothened (SMO) receptor, a key protein of the Hh pathway, has proven effective in treating metastasized basal cell carcinoma. Our lead optimization effort focused on a series of heteroarylamides. We observed that a Me substitution ortho to the heteroaryl groups on an aniline core significantly improved the potency of this series of compounds These findings predated the availability of SMO crystal structure in 2013. Here we retrospectively applied quantum mechanics calculations to demonstrate the o-Me substitution favors the bioactive conformation by inducing a dihedral twist between the heteroaryl rings and the core aniline. The o-Me also makes favorable hydrophobic interactions with key residue side chains in the binding pocket. From this effort, two compounds (AZD8542 and AZD7254) showed excellent pharmacokinetics across multiple preclin. species and demonstrated in vivo activity in abrogating the Hh paracrine pathway as well as anti- tumor effects. After reading the article, we found that the author used 2-Bromo-1H-imidazole(cas: 16681-56-4Category: imidazoles-derivatives)

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. Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Thermal storage density of ionic liquid mixtures: A preliminary study as thermal fluid》 were Mora, Sebastian; Neculqueo, Gloria; Tapia, Ricardo A.; Urzua, Julio I.. And the article was published in Journal of Molecular Liquids in 2019. Formula: C4H6N2 The author mentioned the following in the article:

For the purpose of calculate and compare the variation in thermal storage d., data for the thermal stability, heat capacity, and d. properties of equimolar binary mixtures of 1-octyl-3-methylimidazolium and 1-octyl-2,3-dimethylimidazolium based ionic liquids have been measured. Preliminary anal. of fifteen mixtures obtained from six ionic liquid provide evidence that certain mixtures increase its heat capacity and hence its thermal storage d., offering a viable alternative to materials currently used in solar energy storage. In the part of experimental materials, we found many familiar compounds, such as 1-Methyl-1H-imidazole(cas: 616-47-7Formula: C4H6N2)

1-Methyl-1H-imidazole(cas: 616-47-7) is actively involved in removing acid during the production of diethoxyphenylphosphine. It is used as an intermediate in organic synthesis.Formula: C4H6N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Mechanistic studies of the influence of halogen substituents on the corrosion inhibitive efficiency of selected imidazole molecules: A synergistic computational and experimental approach》 were Abdulazeez, Ismail; Zeino, Aasem; Kee, Choon Wee; Al-Saadi, Abdulaziz A.; Khaled, Mazen; Wong, Ming Wah; Al-Sunaidi, Abdullah A.. And the article was published in Applied Surface Science in 2019. COA of Formula: C3H3BrN2 The author mentioned the following in the article:

Adsorption behavior and corrosion inhibition mechanism of imidazole and its C2-halogenated analogs (with the halogen atoms being Cl, Br or I) on Fe(1 0 0) surface were investigated by DFT periodic slab calculations and electrochem. techniques. DFT calculations revealed that C2-halogenated imidazoles adopt the tilted conformation on Fe surface with a significantly lengthened C-halogen bond and readily undergo facile dissociation at the halo-substitution with calculated adsorption energies -3.95, -3.76 and -3.48 eV for 2-I-Imz, 2-Br-Imz and 2-Cl-Imz, resp. Electrochem. evaluations supported with surface characterization studies showed that the inhibitor mols. adsorb onto mild steel with 2-I-Imz having the highest inhibition efficiency of 83.5%. The trend of observed inhibition efficiencies correlates with adsorption energies and kinetic behavior predicted by the MD approach. The strength of adsorption in the order I >Br > Cl. The present study therefore provides a thorough mechanistic understanding of the role halogen substituents could play on the corrosion inhibitive performance of small organic systems. In addition to this study using 2-Bromo-1H-imidazole, there are many other studies that have used 2-Bromo-1H-imidazole(cas: 16681-56-4COA of Formula: C3H3BrN2) was used in this study.

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. COA of Formula: C3H3BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Polymers (Basel, Switzerland) included an article by Kujawa, Joanna; Rynkowska, Edyta; Fatyeyeva, Kateryna; Knozowska, Katarzyna; Wolan, Andrzej; Dzieszkowski, Krzysztof; Li, Guoqiang; Kujawski, Wojciech. Reference of 1-Methyl-1H-imidazole. The article was titled 《Preparation and characterization of cellulose acetate propionate films functionalized with reactive ionic liquids》. The information in the text is summarized as follows:

The 1-(1,3-diethoxy-1,3-dioxopropan-2-ylo)-3-methylimidazolium bromide (RIL1_Br), 1-(2-etoxy-2 -oxoethyl)-3-methylimidazolium bromide (RIL2_Br), 1-(2-etoxy-2-oxoethyl)-3 -methylimidazolium tetrafluoroborate (RIL3_BF4) ionic liquids were synthesized. Subsequently, the dense cellulose acetate propionate (CAP)-based materials containing from 9 to 28.6 weight% of these reactive ionic liquids were elaborated. Reactive ionic liquids (RILs) were immobilized in CAP as a result of the transesterification reaction. The yield of this reaction was over 90% with respect to the used RIL. The physicochem. properties of resultant films were studied using NMR (NMR), SEM, energy dispersive X-ray (EDX), at. force microscopy (AFM), and thermogravimetric anal. (TGA). The RIL incorporation influenced the morphol. of films by increasing their surface roughness with the rise of RIL content. The thermal stability of CAP-based membranes was dependent on the nature of the ionic liquid Nevertheless, it was proven that CAP films containing RILs were stable up to 120-150°C. Transport properties were characterized by water permeation tests. It was found that the type and the amount of the ionic liquid in the CAP matrix substantially influenced the transport properties of the prepared hybrid materials. In the experiment, the researchers used 1-Methyl-1H-imidazole(cas: 616-47-7Reference of 1-Methyl-1H-imidazole)

1-Methyl-1H-imidazole(cas: 616-47-7) is actively involved in removing acid during the production of diethoxyphenylphosphine. It is used as an intermediate in organic synthesis.Reference of 1-Methyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Polymers (Basel, Switzerland) included an article by Vu-Quang, Hieu; Vinding, Mads Sloth; Nielsen, Thomas; Ullisch, Marcus Goerge; Nielsen, Niels Chr.; Nguyen, Dinh-Truong; Kjems, Jorgen. Application In Synthesis of Di(1H-imidazol-1-yl)methanone. The article was titled 《Pluronic F127-folate coated super paramagenic iron oxide nanoparticles as contrast agent for cancer diagnosis in magnetic resonance imaging》. The information in the text is summarized as follows:

Contrast agents have been widely used in medicine to enhance contrast in magnetic resonance imaging (MRI). Among them, super paramagnetic iron oxide nanoparticles (SPION) have been reported to have low risk in clin. use. In our study, F127-Folate coated SPION was fabricated in order to efficiently target tumors and provide imaging contrast in MRI. SPION alone have an average core size of 15 nm. After stabilizing with Pluronic F127, the nanoparticles reached a hydrodynamic size of 180 nm and dispersed well in various kinds of media. The F127-Folate coated SPION were shown to specifically target folate receptor expressing cancer cells by flow cytometry anal., confocal laser scanning microscope, as well as in vitro MRI. Furthermore, in vivo MRI images have shown the enhanced neg. contrast from the F127-Folate coated SPION in tumor-bearing mice. In conclusion, our F127-Folate coated SPION have shown great potential as a contrast agent in MRI, as well as in the combination with drug delivery for cancer therapy. In the experimental materials used by the author, we found Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Application In Synthesis of Di(1H-imidazol-1-yl)methanone)

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.Application In Synthesis of Di(1H-imidazol-1-yl)methanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2018,Organic & Biomolecular Chemistry included an article by Wang, Jing; Hu, Xuefeng; Wang, Dongli; Xie, Cao; Lu, Weiyue; Song, Jie; Wang, Ruifeng; Gao, Chunli; Liu, Min. Synthetic Route of C3H5N3. The article was titled 《2-Aminoimidazole facilitates efficient gene delivery in a low molecular weight poly(amidoamine) dendrimer》. The information in the text is summarized as follows:

Functional groups have shown great potential in gene delivery. However, a number of the reported functional groups can only overcome one certain physiol. barrier, resulting in limited transfection efficiencies. Based on the structure-activity relationships of both imidazolyl and guanidyl, we designed a novel multifunctional group, 2-aminoimidazole (AM), for gene delivery. On modifying with the AM group, the transfection efficiency of low mol. weight poly(amidoamine) (G2) was 200 times greater than the parent dendrimer in vitro. In contrast, the transfection efficiency of G2 showed a decreasing trend when it was grafted with imidazole. Assays revealed that the AM group played multiple roles in gene delivery, including condensing DNA into monodisperse nanoparticles of 80-90 nm in diameter, achieving nearly ten times higher cellular-uptake efficacy, and enhancing the abilities of endosome/lysosome escape and nuclear localization. What’s more, AM showed low toxicity. These results demonstrate that the AM group could be a promising tool in non-viral gene delivery. After reading the article, we found that the author used 1H-Imidazol-2-amine(cas: 7720-39-0Synthetic Route of C3H5N3)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Synthetic Route of C3H5N3

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

《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

《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

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