Month: February 2023

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

An efficient approach for the deprotection of esters using ionic liquid as nucleophile was written by Wei, Benmei;Zhang, Zhiyong;Dai, Zhiqun;Guan, Jintao. And the article was included in Asian Journal of Chemistry in 2013.Name: 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

An efficient approach for the deprotection of esters was developed using ionic liquid as nucleophile in the presence of protic acid. Using Me benzoate as a model compound, the best result was obtained by the combination of 1-methylimidazolium bromide and methane sulfonic acid with a conversion of 96% after 2 h at 120掳. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Name: 1-Methyl-1H-imidazol-3-ium chloride).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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.Name: 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Prediction of the Formation and Stabilities of Energetic Salts and Ionic Liquids Based on ab Initio Electronic Structure Calculations was written by Gutowski, Keith E.;Holbrey, John D.;Rogers, Robin D.;Dixon, David A.. And the article was included in Journal of Physical Chemistry B in 2005.Recommanded Product: 1-Methyl-4-nitroimidazole This article mentions the following:

A computational approach to predict the thermodn. for forming a variety of imidazolium-based salts and ionic liquids from typical starting materials is described. The gas-phase proton and Me cation acidities of several protonating and methylating agents, as well as the proton and Me cation affinities of many important methyl-, nitro-, and cyano-substituted imidazoles, have been calculated reliably by using the computationally feasible DFT (B3LYP) and MP2 (extrapolated to the complete basis set limit) methods. These accurately calculated proton and Me cation affinities of neutrals and anions are used in conjunction with an empirical approach based on mol. volumes to estimate the lattice enthalpies and entropies of ionic liquids, organic solids, and organic liquids These quantities were used to construct a thermodn. cycle for salt formation to reliably predict the ability to synthesize a variety of salts including ones with potentially high energetic densities. An adjustment of the gas phase thermodn. cycle to account for solid- and liquid-phase chemistries provides the best overall assessment of salt formation and stability. This has been applied to imidazoles (the cation to be formed) with alkyl, nitro, and cyano substituents. The proton and Me cation donors studied were as follows: HCl, HBr, HI, (HO)₂SO₂, HSO₃CF₃ (TfOH), and HSO₃(C₆H₄)CH₃ (TsOH); CH₃Cl, CH₃Br, CH₃I, (CH₃O)₂SO₂, CH₃SO₃CF₃ (TfOCH₃), and CH₃SO₃(C₆H₄)CH₃ (TsOCH₃). As substitution of the cation with electron-withdrawing groups increases, the triflate reagents appear to be the best overall choice as protonating and methylating agents. Even stronger alkylating agents should be considered to enhance the chances of synthetic success. When using the enthalpies of reaction for the gas-phase reactants to form a salt, a cutoff value of -13 kcal mol^-1 or lower (more neg.) should be used as the min. value for predicting whether a salt can be synthesized. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Recommanded Product: 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nucleophilic Aromatic Substitution Reactions Described by the Local Electron Attachment Energy was written by Stenlid, Joakim H.;Brinck, Tore. And the article was included in Journal of Organic Chemistry in 2017.Recommanded Product: 3034-41-1 This article mentions the following:

A local multiorbital electrophilicity descriptor, the local electron attachment energy [E(r)], is used to study the nucleophilic aromatic substitution reactions of S_NAr and VNS (vicarious nucleophilic substitution). E(r) considers all virtual orbitals below the free electron limit and is determined on the mol. isodensity contour of 0.004 at units. Good (R² = 0.83) to excellent (R² = 0.98) correlations are found between descriptor values and exptl. reactivity data for six series of electron deficient arenes. These include homo- and heteroarenes, rings of five to six atoms, and a variety of fluorine, bromine, and hydride leaving groups. The solvent, temperature, and nucleophile are in addition varied across the series. The surface E(r) [E_S(r)] provides reactivity predictions better than those of transition-state calculations for a concerted S_NAr reaction with a bromine nucleofuge, gives correlations substantially stronger than those of LUMO energies, and is overall more reliable than the mol. electrostatic potential. Using E_S(r), one can identify the various electrophilic sites within a mol. and correctly predict isomeric distributions. Since the calculations of E_S(r) are computationally inexpensive, the descriptor offers fast but accurate reactivity predictions for the important nucleophilic aromatic substitution class of reactions. Applications in, e.g., drug discovery, synthesis, and toxicol. studies are envisaged. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Thermodynamics and limiting activity coefficients measurements for organic solutes and water in the ionic liquid 1-dodecyl-3-methylimidzolium bis(trifluoromethylsulfonyl) imide was written by Domanska, Urszula;Wlazlo, Michal. And the article was included in Journal of Chemical Thermodynamics in 2016.Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

Bio-fuels like alcs., including butan-1-ol are produced from biomass by fermentation, and distillation Ionic liquids (ILs) are novel attractive solvents, which can be used for removing butan-1-ol from the aqueous fermentation broth. In this work, the 1-dodecyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}imide, [DoMIM][NTf₂] is proposed as an extractive solvent. The temperature of fusion and the enthalpy of fusion, obtained with DSC, the d. and viscosity of [DoMIM][NTf₂] as a function of temperature have been measured over a temperature range (298.15-368.15) K. The limiting activity coefficients 纬^{鈭?/sup>₁₃, for 65 solutes including alkanes, cycloalkanes, alkenes, alkynes, aromatic hydrocarbons, alcs., water, thiophene, THF, ethers, and ketones in the [DoMIM][NTf₂] were determined by gas-liquid chromatog. at six temperatures from 318.15 K to 368.15 K. The partial molar excess Gibbs energies 螖GE,鈭?/sup>₁, enthalpies 螖HE,鈭?/sup>₁, and entropies 螖SE,鈭?/sup>₁ at infinite dilution were calculated from the exptl. 纬鈭?/sup>₁₃ values obtained over the temperature range. The gas-liquid partition coefficients, K_L were calculated for all solutes and the Abraham solvation parameter model was discussed. The selectivity and capacity for butan-1-ol/water separation problem were calculated from 纬鈭?/sup>₁₃ and compared to literature values for bis{(trifluomethyl)sulfonyl}imide-based ILs with different cations and with all available data for ILs. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).}

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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鈥揅6) is higher than in water and generally decreases with a Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Poly(ionic liquid) Bridge Joining Smectic Lamellar Conducting Channels in Photoelectrochemical Devices as High-Performance Solid-State Electrolytes was written by Wang, Caihong;Li, Xueyong;Zhou, Jiwen;Tian, Wen;Ji, Junyi;Wu, Yong;Tan, Shuai. And the article was included in ACS Applied Energy Materials in 2021.Recommanded Product: 1632-83-3 This article mentions the following:

Nanostructured ionic liquid crystals have emerged as promising electrolytes with the potential to satisfy the demands of both efficient charge transport and stability over conventional liquid electrolytes for advanced energy devices. However, traditional methods via the macroscopic orientation of ionic liquid crystals for charge transport intensification can hardly be achieved during practical device applications. Herein, a simple method was proposed to spontaneously construct long-range continuous conducting channels for significantly improving the charge transport of ionic liquid crystals in the confined space of energy devices. A poly(imidazolium ionic liquid) was designed and in situ prepared in a smectic [C14MIm][I]-based electrolyte for photoelectrochem. device fabrication. The composite solid-state electrolyte self-assembled microphase-segregation nanostructures, wherein the poly(ionic liquid) aggregated at the boundaries of layered smectic polydomains. The imidazolium iodide ions in the poly(ionic liquid) acted as imbedded ion tunnels at domain interfaces via 蟺-蟺 stacking and ionic interaction, which facilitated the charge transport crossing the interfacial gaps to join the intradomain lamellar channels as thermally stable and long-range continuous charge transport pathways. By using the poly(ionic liquid) to bridge the domain-interfacial gaps, the ion conductivity of the ionic liquid crystals was up to 7 times increased with a maximum value of 2.0 x 10^-3 S cm^-1, and the derived dye-sensitized solar cell could operate stably at 70 掳C with a 2-times enhancement and champion efficiency of 8.2%. The approach here was comparable but more processable to traditional methods via the macroscopical orientation of ionic liquid crystals for charge transport intensification within energy devices, which have great potential to develop high-performance solid-state electrolytes to achieve the best balance between efficiency and durability for energy devices. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Recommanded Product: 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) 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 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).Recommanded Product: 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reactions of organic anions. Part 143. Vicarious nucleophilic substitution of hydrogen in imidazole derivatives was written by Makosza, Mieczyslaw;Kwast, Ewa. And the article was included in Bulletin of the Polish Academy of Sciences, Chemistry in 1987.Quality Control of 1-Methyl-4-nitroimidazole This article mentions the following:

Nitroderivatives of imidazole react with carbanions containing leaving groups at the carbanion center yielding products of vicarious nucleophilic substitution of H at positions activated by the nitro group. Thus, nitroimidazole I reacted with PhSO₂CH₂Cl in the presence of KOH in Me₂SO to give derivative II. Some aspects of the orientation pattern of substitution are discussed. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Quality Control of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Quality Control of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A regiospecific rearrangement of 4(5)-substituted 2-phenacylthio-1H-imidazoles to 4-substituted 2-mercapto-1-phenacyl-1H-imidazoles was written by Chakrabarti, Jiban K.;Smith, Colin W.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1991.Formula: C6H8N2O2S This article mentions the following:

4(5)-Substituted 2-phenacylthio-1H-imidazoles I (R = CO₂Et, Ph) thermally rearrange to give 2-mercapto-1-phenacyl-1H-imidazoles II. In the experiment, the researchers used many compounds, for example, Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8Formula: C6H8N2O2S).

Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8) 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鈥揅6) is higher than in water and generally decreases with a 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.Formula: C6H8N2O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of heteroxanthine from a derivative of imidazole was written by Sarasin, J.;Wegmann, E.. And the article was included in Helvetica Chimica Acta in 1924.Application In Synthesis of 1-Methyl-4-nitroimidazole This article mentions the following:

S. and W. describe a new synthesis of 7-methylxanthine from an imidazole derivative, by closing the pyrimidine ring, an operation which has not been previously effected. 1-Methyl-4-nitro-5-chloroimidazole (I) is obtained in theoretical yield from 1-methyl-5-chloroimidazole (b. 200掳) (II) by dissolving in dilute HNO₃ to form the nitrate, treating the latter with cold concentrated H₂SO₄, heating the mixture on the water bath for 2 hrs., and pouring the product on ice; it m. 147-8掳, and is insoluble in acids and dilute alkalies. The isomeric 1-methyl-5-nitro-4-chloroimidazole (III), obtained by the same method from 1-methyl-4-chloroimidazole; m. 77-8掳. I and III are reduced at 0掳 by Sn and HCl to the corresponding methylchloroaminoimidazoles which were not obtained in the pure state. I heated for several hrs. on the H₂O bath in EtOH with 2 mols. KCN and 0.1 mol. KI yields 85% 1-methyl-4-nitro-5-cyanoimidazole (IV), m. 141-2掳, insoluble in acids and dilute alkalies. 1-Methyl-4-nitroimidazole-5-carboxamide (V), obtained in 90% yield when IV is heated for 2 hrs. on the H₂O bath with 8 times its weight of concentrated H₂SO₄ and the product is poured on ice, m. 257-8掳 (decomposes), insoluble in acids and alkalies, saponified with great difficulty; a small amount of the acid (VI) is obtained by prolonged action of concentrated HCl. VI m. 160掳 with evolution of CO₂ and formation of 1-methyl-4-nitroimidazole (VII), m. 133-40掳, which is also obtained by heating V in a sealed tube at 120掳 with HCl. Reduction of VII by Sn and HCl at 0掳 and hydrolysis of the product by heating under pressure with HCl, gives NH₄Cl and sarcosine-HCl, m. 168-9掳; this reaction establishes the constitution of II and VII. V is reduced at 0掳 by Sn and HCl to the corresponding amine, 1-methyl-4-aminoimidazole-5-carboxamide (VIII), m. 184-5掳, decomposed when heated with water or dilute alkalies with evolution of NH₃; HCl salt, m. 214-5掳. 7-Methylxanthine (heteroxanthine) obtained in 38% yield by heating 0.4 g. of VIII for 8 hrs. in a sealed tube at 160-70掳 with an equal weight of CO(OEt)₂, m. 380掳 (browning and evolution of gas). A mixture of the substance with heteroxanthine prepared from theobromine melts at the same temperature The murexide reaction is given with KClO₃ and HCl. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application In Synthesis of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 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.Application In Synthesis 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