Category: imidazoles-derivatives

Chemical Fragments that Hydrogen Bond to Asp, Glu, Arg, and His Side Chains in Protein Binding Sites was written by Chan, A. W. Edith;Laskowski, Roman A.;Selwood, David L.. And the article was included in Journal of Medicinal Chemistry in 2010.Recommanded Product: 26832-08-6 This article mentions the following:

We present an anal. of the chem. fragments from lead-like ligands in the Protein Data Bank (PDB) that form hydrogen bonds to the side chains of Asp, Glu, Arg, and His, which are the most common residues found in ligand binding sites. A fragment is defined as the largest ring assembly containing the atoms involved in hydrogen bonding. In total, 462 fragments were found in 2038 ligands from over 8000 protein-ligand structures in the PDB. The results show which fragments have a higher propensity for interaction with specific side chains. Some fragments interact with Asp but not with Glu, and vice versa, despite these side chains sharing the same chem. moiety. Arg side chains form hydrogen bonds almost exclusively with O-mediated ligands, and the fragments are the most diverse. Hydrogen bond distances from the imidazole of His showed a wider range than the other three amino acids. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Recommanded Product: 26832-08-6).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Recommanded Product: 26832-08-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Enantioselective Conjugate Addition of 2-Acylimidazoles with Nitroalkenes Promoted by Chiral-at-Metal Rhodium(III) Complexes was written by Thota, Ganesh Kumar;Sun, Gui-Jun;Deng, Tao;Li, Yi;Kang, Qiang. And the article was included in Advanced Synthesis & Catalysis in 2018.Recommanded Product: 85692-37-1 This article mentions the following:

An enantioselective conjugate addition of 2-acylimidazoles with nitroalkenes catalyzed by chiral-at-metal rhodium(III) complex under mild reaction conditions was developed, affording versatile γ-nitro ketone skeletons in good yields with excellent enantioselectivities (up to >99% ee). In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Recommanded Product: 85692-37-1).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Recommanded Product: 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

NMR Chemical Shift and Methylation of 4-Nitroimidazole: Experiment and Theory* was written by Backler, Frederick;Sani, Marc Antoine;Separovic, Frances;Vasilyev, Vladislav;Wang, Feng. And the article was included in Australian Journal of Chemistry in 2021.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

Nitroimidazoles and derivatives are a class of active pharmaceutical ingredients (APIs) first introduced sixty years ago. As anti-infection agents, the structure-activity relationships of nitroimidazole compounds have been particularly difficult to study due to their low reduction potentials and unique electronic structures. In this study, we combine dynamic nuclear polarization (DNP)-enhanced solid-state (100K), solid-state (298K), and ¹H-¹³C heteronuclear single quantum coherence (HSQC) solution-state NMR techniques (303K) with d. functional theory (DFT) to study the 1H, 13C, and 15N chem. shifts of 4-nitroimidazole (4-NI) and 1-methyl-4-nitroimidazole (CH₃-4NI). The 4-NI chem. shifts were observed at 119.4, 136.4, and 144.7ppm for 13C, and at 181.5, 237.4, and 363.0ppm for 15N. The measurements revealed that methylation (deprotonation) of the amino nitrogen N(1) of 4-NI had less effect (Δδ=-4.8ppm) on the N(1) chem. shift but was compensated by shielding of the N(3) (Δδ=11.6ppm) in CH₃-4NI. The calculated chem. shifts using DFT for 4-NI and CH₃-4NI agreed well with the exptl. values (within 2%) for the imidazole carbons. However, larger discrepancies (up to 13%) were observed between the calculated and measured 15N NMR chem. shifts for the imidazole nitrogen atoms of both mols., which indicate that effects such as imidazole ring resonant structures and mol. dynamics may also contribute to the nitrogen chem. environment. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

CO₂ Responsive Imidazolium-Type Poly(Ionic Liquid) Gels was written by Zhang, Jing;Xu, Dan;Guo, Jiangna;Sun, Zhe;Qian, Wenjing;Zhang, Ye;Yan, Feng. And the article was included in Macromolecular Rapid Communications in 2016.Reference of 915358-85-9 This article mentions the following:

Poly(ionic liquid) (PIL) gels with CO₂ stimulus responsiveness were synthesized through the copolymerization of an imidazolium-type ionic liquid monomer with 2-(di-Me amino) Et methacrylate. Upon bubbling with CO₂ gas, the prepared PIL solution is converted to a transparent and stable gel, which can be turned back to the initial solution state after N₂ bubbling. The reversible sol-gel phase transition behavior is proved by the reversible values of viscosity and ionic conductivity The possible mechanism for such a reversible sol-gel phase transition is demonstrated by NMR, conductivity, and rheol. measurements. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9Reference of 915358-85-9).

1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Reference of 915358-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ionic-liquid-modified CMK-3 as a support for the immobilization of molybdate ions (MoO₄^2-): Heterogeneous nanocatalyst for selective oxidation of sulfides and benzylic alcohols was written by Hosseini-Eshbala, Fereshteh;Sedrpoushan, Alireza;Breit, Bernhard;Mohanazadeh, Farajollah;Veisi, Hojat. And the article was included in Materials Science & Engineering, C: Materials for Biological Applications in 2020.Computed Properties of C11H20N2 This article mentions the following:

A nanometric carbon CMK-3 modified with octylimidazolium ionic liquid (OctIm) and MoO₄^2- as a new hybrid catalyst was synthesized. The study is the first to report a successful immobilization of MoO₄^2- on the CMK-3/OctIm as a hybrid nanocatalyst. A variety of anal. methods were utilized to determine the properties of the structure and morphol. of the synthesized nanocatalyst [CMK-3/OctIm/ MoO₄^2-]. The anal. techniques were transmission electron microscopy (TEM), scanning electron microscope (SEM), energy-dispersive X-ray spectroscopy (EDS), inductively coupled plasma (ICP), X-ray diffraction (XRD), N₂ isotherms (BET), IR spectroscopy and thermogravimetric anal. (TGA). CMK-3/OctIm/ MoO₄^2- hybrid catalyst demonstrated a considerable catalytic activity. It is a recyclable nanocatalyst that is utilized to chemoselectively oxidize different types of sulfides RSR¹ (R = Me, Ph, prop-2-en-1-yl, etc.; R¹ = Me, Ph, cyanomethyl, etc.) and thianthrene to the corresponding sulfoxides RS(O)R¹ and thianthrene,5,10-dioxide and benzylic alcs. R²CH₂OH (R² = Ph, 3,4,5-trimethoxyphenyl, 3-chlorophenyl, etc.) to aldehydes R²CHO using the green oxidant, hydrogen peroxide (H₂O₂) in high-yields. With a little leaching and variation in activity, it is possible to recover and reuse the catalyst frequently. A combination of molybdate anion and the CMK-3 order mesoporous carbon resulted in an improvement in the performance of catalysis and ease of separation for the reaction procedure. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Computed Properties of C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Computed Properties of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Alkylimidazolium Based Ionic Liquids: Impact of Cation Symmetry on Their Nanoscale Structural Organization was written by Rocha, Marisa A. A.;Neves, Catarina M. S. S.;Freire, Mara G.;Russina, Olga;Triolo, Alessandro;Coutinho, Joao A. P.;Santos, Luis M. N. B. F.. And the article was included in Journal of Physical Chemistry B in 2013.Synthetic Route of C18H31F6N3O4S2 This article mentions the following:

Aiming at evaluating the impact of the cation symmetry on the nanostructuration of ionic liquids (ILs), in this work, densities and viscosities as a function of temperature and small-wide angle X-ray scattering (SWAXS) patterns at ambient conditions were determined and analyzed for 1-alkyl-3-methylimidazolium bis-(trifluoromethylsulfonyl)-imide (asym.) and 1,3-dialkylimidazolium bis-(trifluoromethylsulfonyl)-imide (sym.) series of ionic liquids The sym. IL series, [C_N/2C_N/2i.m.]-[NTf₂], presents lower viscosities than the asym. [C_N-1C₁i.m.]-[NTf₂] counterparts. For ionic liquids from [C₁C₁i.m.]-[NTf₂] to [C₆C₆i.m.]-[NTf₂], an odd-even effect in the viscosity along the cation alkyl side chain length was observed, in contrast with a linear increase found for the ones ranging between [C₆C₆i.m.]-[NTf₂] and [C₁₀C₁₀i.m.]-[NTf₂]. The anal. of the viscosity data along the alkyl side chain length reveals a trend shift that occurs at [C₆C₁i.m.]-[NTf₂] for the asym. series and at [C₆C₆i.m.]-[NTf₂] for the sym. series. These results are further supported by SWAXS measurements at ambient conditions. The gathered data indicate that both asym. and sym. members are characterized by the occurrence of a distinct degree of mesoscopic structural organization above a given threshold in the side alkyl chain length, regardless the cation symmetry. The data also highlight a difference in the alkyl chain dependence of the mesoscopic cluster sizes for sym. and asym. cations, reflecting a different degree of interdigitation of the aliphatic tails in the two families. The trend shift found in this work is related to the structural segregation in the liquid after a critical alkyl length size (CALS) is attained and has particular relevance in the cation structural isomerism with higher symmetry. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Synthetic Route of C18H31F6N3O4S2).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Synthetic Route of C18H31F6N3O4S2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Design and Application of a Low-Temperature Continuous Flow Chemistry Platform was written by Newby, James A.;Blaylock, D. Wayne;Witt, Paul M.;Pastre, Julio C.;Zacharova, Marija K.;Ley, Steven V.;Browne, Duncan L.. And the article was included in Organic Process Research & Development in 2014.Quality Control of 1-(1-Methyl-1H-imidazol-2-yl)ethanone This article mentions the following:

A flow reactor platform technol. applicable to a broad range of low temperature chem. is reported. The newly developed system captures the essence of running low temperature reactions in batch and represents this as a series of five flow coils, each with independently variable volume The system was initially applied to the functionalization of alkynes, Grignard addition reactions, heterocycle functionalization, and heteroatom acetylation. This new platform has then been used in the preparation of a 20-compound library of polysubstituted, fluorine-containing aromatic substrates from a sequential metalation-quench procedure and can be readily adapted to provide gaseous electrophile inputs such as carbon dioxide using a tube-in-tube reactor. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Quality Control of 1-(1-Methyl-1H-imidazol-2-yl)ethanone).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Quality Control of 1-(1-Methyl-1H-imidazol-2-yl)ethanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The Gelling Ability of Some Diimidazolium Salts: Effect of Isomeric Substitution of the Cation and Anion was written by D’Anna, Francesca;Vitale, Paola;Ferrante, Francesco;Marullo, Salvatore;Noto, Renato. And the article was included in ChemPlusChem in 2013.Electric Literature of C11H20N2 This article mentions the following:

The gelling ability of some geminal imidazolium salts was studied both in organic solvents and in water solution Organic salts differing either in the cation or anion structure were taken into account. In particular, the effects on the gel-phase formation of isomeric substitution on the cation or anion and of the use of mono- or dianions were evaluated. As far as the cation structure is concerned, isomeric cations, such as 3,3′-di-n-octyl-1,1′-(1,4-phenylenedimethylene)diimidazolium and 3,3′-di-n-octyl-1,1′-(1,3-phenylenedimethylene)diimidazolium, were used. However, in addition to the bromide anion, isomeric dianions, such as the 1,5- and 2,6-naphthalenedisulfonate anions, were also examined After preliminary gelation tests, different factors affecting the obtained gel phases, such as the nature of the solvent, organogelator concentrations, and action of external stimuli, were analyzed. The gel-phase formation was also studied as a function of time, by using resonance light scattering measurements. Gel morphologies were analyzed by SEM. To further support the understanding of the different behavior shown by the isomeric cations, some representative ion pairs were analyzed by DFT-based studies. The collected data underline the significant role played by isomeric substitution of both cation and anion structures in determining the gelling capability of the studied salts, as well as the properties of the gel phases. Finally, DFT studies were helpful in the identification of the structural features affecting the self-assembly. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Electric Literature of C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Electric Literature of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Intracerebroventricular Administration of Metformin Inhibits Ghrelin-Induced Hypothalamic AMP-Kinase Signalling and Food Intake was written by Stevanovic, Darko;Janjetovic, Kristina;Misirkic, Maja;Vucicevic, Ljubica;Sumarac-Dumanovic, Mirjana;Micic, Dragan;Starcevic, Vesna;Trajkovic, Vladimir. And the article was included in Neuroendocrinology in 2012.Computed Properties of C4H5N3O This article mentions the following:

Background/Aims: The antihyperglycemic drug metformin reduces food consumption through mechanisms that are not fully elucidated. The present study investigated the effects of intracerebroventricular administration of metformin on food intake and hypothalamic appetite-regulating signaling pathways induced by the orexigenic peptide ghrelin. Methods: Rats were injected intracerebroventricularly with ghrelin (5 μg), metformin (50, 100 or 200 μg), 5-amino-imidazole-4-carboxamide 1-β-D-ribofuranoside (AICAR, 25 μg) and L-leucine (1 μg) in different combinations. Food intake was monitored during the next 4 h. Hypothalamic activation of AMP-activated protein kinase (AMPK), acetyl-CoA carboxylase (ACC), regulatory-associated protein of mTOR (Raptor), mammalian target of rapamycin (mTOR) and p70 S6 kinase 1 (S6K) after 1 h of treatment was analyzed by immunoblotting. Results: Metformin suppressed the increase in food consumption induced by intracerebroventricular ghrelin in a dose-dependent manner. Ghrelin increased phosphorylation of hypothalamic AMPK and its targets ACC and Raptor, which was associated with the reduced phosphorylation of mTOR. The mTOR substrate, S6K, was activated by intracerebroventricular ghrelin despite the inhibition of mTOR. Metformin treatment blocked ghrelin-induced activation of hypothalamic AMPK/ACC/Raptor and restored mTOR activity without affecting S6K phosphorylation. Metformin also reduced food consumption induced by the AMPK activator AICAR while the ghrelin-triggered food intake was inhibited by the mTOR activator L-leucine. Conclusion: Metformin could reduce food intake by preventing ghrelin-induced AMPK signaling and mTOR inhibition in the hypothalamus. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Computed Properties of C4H5N3O).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Computed Properties of C4H5N3O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A reactive oxygen species Ca²⁺ signalling pathway identified from a chemical screen for modifiers of sugar-activated circadian gene expression was written by Li, Xiang;Deng, Dongjing;Cataltepe, Gizem;Roman, Angela;Buckley, Christopher R.;Cassano Monte-Bello, Carolina;Skyricz, Aleksandra;Caldana, Camila;Haydon, Michael J.. And the article was included in New Phytologist in 2022.Electric Literature of C33H34N6O6 This article mentions the following:

Sugars are essential metabolites for energy and anabolism that can also act as signals to regulate plant physiol. and development. Exptl. tools to disrupt major sugar signalling pathways are limited. We performed a chem. screen for modifiers of activation of circadian gene expression by sugars to discover pharmacol. tools to investigate and manipulate plant sugar signalling. Using a library of com. available bioactive compounds, we identified 75 confident hits that modified the response of a circadian luciferase reporter to sucrose in dark-adapted Arabidopsis thaliana seedlings. We validated the transcriptional effect on a subset of the hits and measured their effects on a range of sugar-dependent phenotypes for 13 of these chems. Chems. were identified that appear to influence known and unknown sugar signalling pathways. Pentamidine isethionate was identified as a modifier of a sugar-activated Ca2+ signal that acts as a calmodulin inhibitor downstream of superoxide in a metabolic signalling pathway affecting circadian rhythms, primary metabolism and plant growth. Our data provide a resource of new exptl. tools to manipulate plant sugar signalling and identify novel components of these pathways. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Electric Literature of C33H34N6O6).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Electric Literature of C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem