Category: imidazoles-derivatives

《Temperature, Composition, and Alkyl Chain-Dependent Molecular Interactions between Imidazolium-Based Ionic Liquids with N-Methylaniline and N-Ethylaniline: Experimental and Theoretical Study》 was published in Journal of Chemical & Engineering Data in 2020. These research results belong to Master, Zubin; Malek, Naved I.. Synthetic Route of C8H15BF4N2 The article mentions the following:

Ionic liquids (ILs), an alternative to conventional mol. organic solvents, have attracted the attention of the scientific community because of their tunable unique physicochem. properties. Among the tested strategies, addition of co-solvents is the most convenient choice to alter the physicochem. properties of ILs for their industrial applications. In the present article, we have measured the d. (ρ), speeds of sound (u), and refractive index (nD) for six binary mixtures of N-methylaniline (NMA) and N-ethylaniline (NEA) + BmimBF4 + HmimBF4 + OmimBF4 over the entire range of composition and at temperatures ranging from 293.15 to 323.15 K at 5 K intervals and at atm. pressure. Excess molar volume (VmE), excess molar isentropic compressibility (Ks,mE), and deviation in the refractive index (ΔφnD) on volume fraction basis were calculated from these measured thermophys. properties. Influence of temperature on the excess and deviation properties has been studied. VmE, Ks,mE, and ΔφnD were fitted to the Redlich-Kister polynomial equation, and the parameters for the binary coefficients are reported. The influence of the alkyl chain length of ILs on the thermophys. properties of the mixtures of secondary amines was studied. We have discussed the intermol. interactions between the ILs and amine mols. using well-known arguments. We further predicted the refractive indexes of the studied mixtures using various mixing rules, and the resulting values have been compared with the exptl. values through the standard deviation. Exptl. calculated excess molar volumes have been compared with the predicted values of the Prigogine-Flory-Patterson theory and the extended real association model at 298.15 K. In the experiment, the researchers used many compounds, for example, 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6Synthetic Route of C8H15BF4N2)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. A multidisciplinary study on lonic liquids is emerging, including chemistry, materials science, chemical engineering, and environmental science. More specifically, some important fundamental viewpoints are now different from the original concepts, as insights into the nature of lonic liquids become deeper. For example, the physicochemical properties of lonic liquids are now recognized as ranging broadly from the oft quoted “nonvolatile, non-flammable, and air and water stable” to those that are distinctly volatile, flammable, and unstable. Synthetic Route of C8H15BF4N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Alkylated benzimidazoles: Design, synthesis, docking, DFT analysis, ADMET property, molecular dynamics and activity against HIV and YFV》 was published in Computational Biology and Chemistry in 2020. These research results belong to Srivastava, Ritika; Gupta, Sunil K.; Naaz, Farha; Sen Gupta, Parth Sarthi; Yadav, Madhu; Singh, Vishal Kumar; Singh, Anuradha; Rana, Malay Kumar; Gupta, Satish Kumar; Schols, Dominique; Singh, Ramendra K.. Related Products of 4857-06-1 The article mentions the following:

A series of alkylated benzimidazole derivatives I [R1 = H, Br, NO2; R2 = H, Br, NO2; R3 = (CH2)2OH, (CH2)3OH] was synthesized and screened for their anti-HIV, anti-YFV, and broad-spectrum antiviral properties. The physicochem. parameters and drug-like properties of the compounds were assessed first, and then docking studies and MD simulations on HIV-RT allosteric sites were conducted to find the possible mode of their action. DFT anal. was also performed to confirm the nature of the hydrogen bonding interaction of active compounds The in silico studies indicated that the mols. behaved like possible NNRTIs. The nature – polar or non-polar and position of the substituent present at fifth, sixth, and N-1 positions of the benzimidazole moiety played an important role in determining the antiviral properties of the compounds Among the various compounds, I (R1 = R2 = Br; R3 = (CH2)2OH) showed anti-HIV activity with an appreciably low IC50 value as 0.386 x 10-5μM. Similarly, compound I (R1 = NO2; R2 = H; R3 = (CH2)3OH), showed excellent inhibitory property against the yellow fever virus (YFV) with EC50 value as 0.7824 x 10-2μM. In the experiment, the researchers used many compounds, for example, 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Related Products of 4857-06-1)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.Related Products of 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Pendant Alkoxy Groups on N-Aryl Substitutions Drive the Efficiency of Imidazolylidene Catalysts for Homoenolate Annulation from Enal and Aldehyde》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Kyan, Ryuji; Sato, Kohei; Mase, Nobuyuki; Narumi, Tetsuo. Application In Synthesis of 1,3-Dimesityl-1H-imidazol-3-ium chloride The article mentions the following:

Hydrogen-transfer in the tetrahedral intermediate generated from an imidazolylidene catalyst and α,β-unsaturated aldehyde forms a conjugated Breslow intermediate. This is a critical step affecting the efficiency of the NHC-catalyzed γ-butyrolactone formation via homoenolate addition to aryl aldehydes. A novel type of imidazolylidene catalyst with pendant alkoxy groups on the ortho-N-aryl groups is described. Catalyst of this sort facilitates the formation of the conjugated Breslow intermediate. Studies of the rate constants for homoenolate annulation affording γ-butyrolactones, reveal that introduction of the oxygen atoms in the appropriate position of the N-aryl substituents can increase the efficiency of imidazolylidene catalysts. Structural and mechanistic studies revealed that pendant alkoxy groups can be located close to the proton of the tetrahedral intermediate, thereby facilitating the proton transfer. The results came from multiple reactions, including the reaction of 1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Application In Synthesis of 1,3-Dimesityl-1H-imidazol-3-ium chloride)

1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8) is a ligand for arylation of aldehydes and for carbene catalyzed intermolecular arylation of C-H bonds. It is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases.Application In Synthesis of 1,3-Dimesityl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Intermolecular, Branch-Selective, and Redox-Neutral Cp*IrIII-Catalyzed Allylic C-H Amidation》 were Knecht, Tobias; Mondal, Shobhan; Ye, Jian-Heng; Das, Mowpriya; Glorius, Frank. And the article was published in Angewandte Chemie, International Edition in 2019. SDS of cas: 530-62-1 The author mentioned the following in the article:

Herein, we report the redox-neutral, intermol., and highly branch-selective amidation of allylic C-H bonds enabled by Cp*IrIII catalysis. A variety of readily available carboxylic acids were converted into the corresponding dioxazolones and efficiently coupled with terminal and internal olefins in high yields and selectivities. Mechanistic investigations support the formation of a nucleophilic IrIII-allyl intermediate rather than the direct insertion of an Ir-nitrenoid species into the allylic C-H bond. In the experiment, the researchers used many compounds, for example, Di(1H-imidazol-1-yl)methanone(cas: 530-62-1SDS of cas: 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.SDS of cas: 530-62-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Label-free detection of exosomes using a surface plasmon resonance biosensor》 were Sina, Abu Ali Ibn; Vaidyanathan, Ramanathan; Wuethrich, Alain; Carrascosa, Laura G.; Trau, Matt. And the article was published in Analytical and Bioanalytical Chemistry in 2019. Quality Control of 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid The author mentioned the following in the article:

The development of a sensitive and specific detection platform for exosomes is highly desirable as they are believed to transmit vital tumor-specific information (mRNAs, microRNAs, and proteins) to remote cells for secondary metastasis. Herein, the authors report a simple method for the real-time and label-free detection of clin. relevant exosomes using a surface plasmon resonance (SPR) biosensor. The authors’ method shows high specificity in detecting BT474 breast cancer cell-derived exosomes particularly from complex biol. samples (e.g. exosome spiked in serum). This approach exhibits high sensitivity by detecting as low as 8280 exosomes/μL which may potentially be suitable for clin. anal. The authors believe that this label-free and real-time method along with the high specificity and sensitivity may potentially be useful for clin. settings. In addition to this study using 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid, there are many other studies that have used 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5Quality Control of 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid) was used in this study.

5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5) may be used to elute proteins from avidin/streptavidin resins. It has been used for culturing of oligodendrocytes.Quality Control of 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid And it has been used for blocking endogenous biotin during immunohistology procedures.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2017,Abdellattif, Magda H.; Eissa, A. M. F.; Mohamed, H. M. published 《Synthesis of anionic surface active agents containing heterocyclic moiety from long chain fatty alcohols》.Journal of Advances in Chemistry published the findings.Safety of 1H-Imidazol-2-amine The information in the text is summarized as follows:

A series of novel groups of anionic surface active agent were synthesized. Synthesis of these surfactants via the reaction of long chain fatty alcs. (octyl, decyl and dodecyl) with maleic anhydride to give monoester. The monoester chloride reacted with amino derivatives of heterocyclic rings followed by addition of NaHSO3. The surface tension, interfacial tension; Kraft point, emulsifying and wetting power were evaluated. Stability to hydrolysis, biodegradability and biol. activities were measured. A comparison studies between the chem. structures and the results were done. After reading the article, we found that the author used 1H-Imidazol-2-amine(cas: 7720-39-0Safety of 1H-Imidazol-2-amine)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Safety of 1H-Imidazol-2-amine

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2017,Draughn, G. Logan; Allen, C. Leigh; Routh, Patricia A.; Stone, Maria R.; Kirker, Kelly R.; Boegli, Laura; Schuchman, Ryan M.; Linder, Keith E.; Baynes, Ronald E.; James, Garth; Melander, Christian; Pollard, Angela; Cavanagh, John published 《Evaluation of a 2-aminoimidazole variant as adjuvant treatment for dermal bacterial infections》.Drug Design, Development and Therapy published the findings.Quality Control of 1H-Imidazol-2-amine The information in the text is summarized as follows:

2-Aminoimidazole (2-AI)-based compounds have been shown to efficiently disrupt biofilm formation, disperse existing biofilms, and resensitize numerous multidrug-resistant bacteria to antibiotics. Using Pseudomonas aeruginosa and Staphylococcus aureus, we provide initial pharmacol. studies regarding the application of a 2-AI as a topical adjuvant for persistent dermal infections. In vitro assays indicated that the 2-AI H10 is nonbactericidal, resensitizes bacteria to antibiotics, does not harm the integument, and promotes wound healing. Furthermore, in vivo application of H10 on swine skin caused no gross abnormalities or immune reactions. Taken together, these results indicate that H10 represents a promising lead dermal adjuvant compound The experimental process involved the reaction of 1H-Imidazol-2-amine(cas: 7720-39-0Quality Control of 1H-Imidazol-2-amine)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Quality Control of 1H-Imidazol-2-amine

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2010,Garton, Neil; Bailey, Nick; Bamford, Mark; Demont, Emmanuel; Farre-Gutierrez, Irene; Hutley, Gail; Bravi, Gianpaolo; Pickering, Paula published 《Discovery of biaryl inhibitors of H+/K+ ATPase》.Bioorganic & Medicinal Chemistry Letters published the findings.Synthetic Route of C3H3BrN2 The information in the text is summarized as follows:

We report the identification of a novel biaryl template for H+/K+ ATPase inhibition. Evaluation of critical SAR features within the biaryl imidazole framework and the use of pharmacophore modeling against known imidazopyridine and azaindole templates suggested that the geometry of the mol. is key to achieving activity. Herein we present our work optimizing the potency of the mol. through modifications and substitutions to each of the ring systems. In particular sub-micromolar potency is achieved with (4b) presumably through a proposed intramol. hydrogen bond that ensures the required imidazole basic center is appropriately located. In the experiment, the researchers used many compounds, for example, 2-Bromo-1H-imidazole(cas: 16681-56-4Synthetic Route of C3H3BrN2)

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. Synthetic Route of C3H3BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Chemistry – A European Journal included an article by Rottschaefer, Dennis; Sharma, Mahendra K.; Neumann, Beate; Stammler, Hans-Georg; Andrada, Diego M.; Ghadwal, Rajendra S.. Quality Control of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride. The article was titled 《A Modular Access to Divinyldiphosphenes with a Strikingly Small HOMO-LUMO Energy Gap》. The information in the text is summarized as follows:

The olefinic C-H bond functionalization of (NHC)CHPh (NHC = IPr =C{(NAr)CH}2 1; SIPr = C{(NAr)CH2}2 2; Ar = 2,6-iPr2C6H3), derived from classical N-heterocyclic carbenes (NHCs), with PCl3 affords the dichlorovinylphosphines {(NHC)C(Ph)}PCl2 (NHC = IPr 3, SIPr 4). Two-electron reduction of 3 and 4 with magnesium leads to the formation of the divinyldiphosphenes [{(NHC)C(Ph)}P]2 (NHC = IPr 5, SIPr 6) as crystalline solids. Unlike literature-known diphosphenes, which are mostly yellow or orange, 5 is a green whereas 6 is a purple solid. Although the P:P bond lengths of 5 (2.062(1)) and 6 (2.055(1) Å) are comparable to those of the known diphosphenes (2.02-2.08 Å), the C-P bond lengths of 5 (1.785(1)) and 6 (1.797(1) Å) are, however, considerably shorter than a Csp2-P single bond length (1.85 Å), indicating a considerable π-conjugation between C:C and P:P moieties. The HOMO-LUMO energy gap for 5 (4.15) and 6 (4.52 eV) is strikingly small and thus the narrowest among the diphosphenes (>4.93 eV) reported as yet. Consequently, 5 readily undergoes P:P bond cleavage at room temperature on treatment with sulfur to form the unique dithiophosphorane {(IPr)C(Ph)}P(S)2 7. Interestingly, reaction of 5 with selenium gives the selenadiphosphirane [{(IPr)C(Ph)}P]2Se 8 with an intact P-P bond. In the experimental materials used by the author, we found 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Quality Control 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) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Quality Control 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

《Simple Synthetic Routes to N-Heterocyclic Carbene Gold(I)-Aryl Complexes: Expanded Scope and Reactivity》 was written by Tzouras, Nikolaos V.; Saab, Marina; Janssens, Wim; Cauwenbergh, Thibault; Van Hecke, Kristof; Nahra, Fady; Nolan, Steven P.. Category: imidazoles-derivatives And the article was included in Chemistry – A European Journal on April 28 ,2020. The article conveys some information:

Transmetalation of arylboronic acids with gold(I) NHC chlorides [LAuCl] afforded arylgold complexes [LAuAr] (Ar = substitutted Ph, 1-naphthyl, 2-furyl; L = 1,3-bis(diisopropylphenyl)-2-imidazolylidene, 4,5-dichloro-1,3-bis(diisopropylphenyl)-2-imidazolylidene, 1,3-di-1-adamantyl-2-imidazolylidene, 1,3-di-tert-butyl-2-imidazolylidene, PPh3). Reactivity of arylgold complexes [LAuAr] towards OH-, NH- and CH-acids (HX) was explored, giving access to complexes [LAuX]. The discovery of sustainable and scalable synthetic protocols leading to gold-aryl compounds bearing N-heterocyclic carbene (NHC) ligands sparked an investigation of their reactivity and potential utility as organometallic synthons. The use of a mild base and green solvents provide access to these compounds, starting from widely available boronic acids and various [Au(NHC)Cl] complexes, with reactions taking place under air, at room temperature and leading to high yields with unprecedented ease. One compound, (N,N’-bis[2,6-(diisopropyl)phenyl]-2-imidazolylidene)(4-methoxyphenyl)gold, ([Au(IPr)(4-MeOC6H4)]), was synthesized on a multigram scale and used to gauge the reactivity of this class of compounds towards C-H/N-H bonds and with various acids, revealing simple pathways to gold-based species that possess attractive properties as materials, reagents and/or catalysts. In the experiment, the researchers used many compounds, for example, Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Category: imidazoles-derivatives)

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Category: imidazoles-derivatives 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