Month: February 2023

Toward Designing “Sweet” Ionic Liquids Containing a Natural Terpene Moiety as Effective Wood Preservatives was written by Feder-Kubis, Joanna;Zabielska-Matejuk, Jadwiga;Stangierska, Anna;Przybylski, Piotr;Jacquemin, Johan;Geppert-Rybczynska, Monika. And the article was included in ACS Sustainable Chemistry & Engineering in 2019.Category: imidazoles-derivatives This article mentions the following:

This study is focused on the utilization of naturally occurring terpene alc. in the synthesis of ionic liquids (ILs) and their application potential in wood protection. A new series of ILs containing a natural, renewable source of (-)-menthol in the cation and a saccharinate derivative as the anion were obtained with a high yield under mild process conditions. The potential applications of synthesized compounds that belong to surface-active compounds were assessed for wood preservation, and they showed pos. results. Laboratory tests of their activity against fungi and saccharinate-based chiral ionic liquid (CIL) bonding with Scots pine (Pinus sylvestris L.) wood are described. The biol. results for salts with alkyl substituents ranging from pentyl to octyl chains are very promising, and their activity is similar to, and even higher than, that of the commonly used material benzalkonium chloride. The fungicidal values of saccharinate-based CILs against Coniophora puteana ranged from 2.75 to 4.4 kg m^-3 and were lower than those of com. benzalkonium chloride. Moreover, those salts penetrate to some extent into pine wood, which strongly increases their potential for use in wood industries. The attenuated total reflectance IR spectroscopy technique was used to characterize the fixing mechanism of the chiral “sweet” salts in the wood structure, and the CIL penetration depth into Scots pine wood was tested. These results were completed with the surface properties of the investigated saccharinates, the surface tension measurements, and contact angles of ILs on wood. The corrosiveness study of imidazolium saccharinate salt showed low aggressiveness against carbon steel, moreover, lower than that of IL with nitrate anion, didecyldimethylammonium nitrate, and com. used benzalkonium chloride. The incorporation of a saccharinate anion into the IL structure may eliminate this unfavorable property of com. protective agents based on ILs. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Category: imidazoles-derivatives).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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).Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Chemoselective iodination of 6-substituted imidazo[1,2-a]pyridine was written by Zhao, Chunshen;Li, Fei;Yang, Shuo;Liu, Li;Huang, Zhuyan;Chai, Huifang. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2018.Computed Properties of C7H5N3O2 This article mentions the following:

3- And 8-Iodoimidazo[1,2-a]pyridines were synthesized from imidazo[1,2-a]pyridines under different substitution conditions. The mol. electrostatic potential calculations were performed to investigate the chemoselectivity of the substitution reaction. The mol. structures of the target compounds were characterized by single crystal X-ray diffraction anal. In the experiment, the researchers used many compounds, for example, 6-Nitroimidazo[1,2-a]pyridine (cas: 25045-82-3Computed Properties of C7H5N3O2).

6-Nitroimidazo[1,2-a]pyridine (cas: 25045-82-3) 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. 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.Computed Properties of C7H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

TEMPO-Mediated Synthesis of N-(Fluoroalkyl)imidazolones via Reaction of Imidazoles with Iodofluoroacetate was written by Chen, Jia-Hao;Ahmed, Wasim;Li, Ming-Hua;Li, Zhao-Dong;Cui, Zi-Ning;Tang, Ri-Yuan. And the article was included in Advanced Synthesis & Catalysis in 2020.Electric Literature of C8H8N2 This article mentions the following:

A TEMPO-mediated oxidative copper-catalyzed synthesis of N-(fluoroalkyl)imidazolones e.g., I via the radical addition of imidazoles such as 6-bromo-3-methyl-3H-imidazo[4,5-b]pyridine, 1-phenylimidazole, 5-bromo-1-methylbenzimidazole, etc. with iodofluoroacetate ICH(F)C(O)OCH₂CH₃ was reported. A possible key intermediate involving TEMPO was observed by ESI-MS. Also found that aerobic oxidation conditions were effective for the transformation in the presence of a copper catalyst, enabling access to a number of N-(fluoroalkyl)imidazolones I in moderate to good yields. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Electric Literature of C8H8N2).

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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Electric Literature of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Identification of new process-related impurity in the key intermediate in the synthesis of TCV-116 was written by Testen, Ana;Plevnik, Miha;Stefane, Bogdan;Cigic, Irena Kralj. And the article was included in Acta Pharmaceutica (Warsaw, Poland) in 2019.Synthetic Route of C33H34N6O6 This article mentions the following:

Development of safe and effective drugs requires complete impurity evaluation and, therefore, knowledge about the formation and elimination of impurities is necessary. During impurity profiling of a key intermediate during synthesis of candesartan cilexetil (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, TCV-116), a novel compound, which had not been reported previously, was observed Structural elucidation of impurity was achieved by liquid chromatog. hyphenated to different high resolution mass analyzers. Based on exact mass measurements and fragmentation pattern, a chloro alkyl carbonate ester analog of the intermediate was identified. Structure of the impurity was confirmed by mass spectro-metric and NMR analyses of the target substance. Identified impurity could represent a hazard if it is transferred to the final API stage and its presence should be kept below allowed limits. Further investigation could reveal whether bis(1-chloroethyl) carbonate is a precursor to impurity formation. Therefore, synthesis should be regulated so as to minimize impurity production Anal. of the final product indicated that the amount of impurity did not exceed 50 mg L^-1, which represents the detection limit, determined according to the signal/noise ratio. 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: 145040-37-5Synthetic Route 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. 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).Synthetic Route of C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Solvatochromism of Heteroaromatic Compounds: XIX. Factors Affecting Quantitative Characteristics of Solvatochromism in Aprotic Inert Media was written by Turchaninov, V. K.;Vokin, A. I.;Aksamentova, T. N.;Krivoruchka, I. G.;Shulunova, A. M.;Andriyankova, L. V.. And the article was included in Russian Journal of General Chemistry (Translation of Zhurnal Obshchei Khimii) in 2003.Computed Properties of C4H5N3O2 This article mentions the following:

The effects of aprotic inert media on the electronic absorption spectra of aromatic nitro compounds p-NO₂C₆H₄R were used as evidence for the linear correlation between the slope s_a of the solvatochromism equations ν_max = ν₀ + s_aπ^* and the dipole moments of the mols. in their ground electronic state μ_g. A linear correlation was established between ν₀ and the first ionization potential of subunits PhR. A new approach to estimating the dipole moment of electronically excited mols. (μ_e) for mols. like p-NO₂C₆H₄R from the correlation μ_e = rμ_g was proposed. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Computed Properties of C4H5N3O2).

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 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.Computed Properties of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Syntheses of some N-alkylated-2-substituted imidazoles was written by Moazzam, Muhammad;Parrick, J.. And the article was included in Journal of the Chemical Society of Pakistan in 1988.Related Products of 85692-37-1 This article mentions the following:

N-Substituted imidazoles were prepared by modifications of known methods. Some substitutions, e.g. acetylation, at the 2-position of these compounds were carried out. A few hydrazones of 1-triphenylmethylimidazole-2-carboxaldehyde were also prepared Reaction of the 2-aldehyde with Et nitroacetate is described. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Related Products of 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 This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Related Products of 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of new formyl halo N-methylimidazole derivatives was written by El Borai, M.;Moustafa, A. H.;Anwar, M.;Ghattas, A. G.. And the article was included in Croatica Chemica Acta in 1981.HPLC of Formula: 25676-75-9 This article mentions the following:

Title compounds [I, R, R¹, R² = CHO, Br, H (II), Br, CHO, H; H, Br, CHO; CHO, H, Br; CHO, Br, Br] were prepared E. g., formylation of I (R = Br, R¹ = R² = H) followed by bromination gave II. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9HPLC of Formula: 25676-75-9).

4-Bromo-1-methylimidazole (cas: 25676-75-9) 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.HPLC of Formula: 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Defining Structure-Functional Selectivity Relationships (SFSR) for a Class of Non-Catechol Dopamine D₁ Receptor Agonists was written by Martini, Michael L.;Liu, Jing;Ray, Caroline;Yu, Xufen;Huang, Xi-Ping;Urs, Aarti;Urs, Nikhil;McCorvy, John D.;Caron, Marc G.;Roth, Bryan L.;Jin, Jian. And the article was included in Journal of Medicinal Chemistry in 2019.COA of Formula: C7H5BrN2 This article mentions the following:

G protein-coupled receptors (GPCRs) are capable of downstream signaling through distinct noncanonical pathways such as β-arrestins in addition to the canonical G protein-dependent pathways. GPCR ligands that differentially activate the downstream signaling pathways are termed functionally selective or biased ligands. A class of novel non-catechol G protein-biased agonists of the dopamine D₁ receptor (D₁R) was recently disclosed. We conducted the first comprehensive structure-functional selectivity relationship study measuring G_S and β-arrestin2 recruitment activities focused on four regions of this scaffold, resulting in over 50 analogs with diverse functional selectivity profiles. Some compounds became potent full agonists of β-arrestin2 recruitment, while others displayed enhanced G_S bias compared to the starting compound Pharmacokinetic testing of an analog with an altered functional selectivity profile demonstrated excellent blood-brain barrier penetration. This study provides novel tools for studying ligand bias at D₁R and paves the way for developing the next generation of biased D₁R ligands. In the experiment, the researchers used many compounds, for example, 5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1COA of Formula: C7H5BrN2).

5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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.COA of Formula: C7H5BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Heterogeneous Structures of Ionic Liquids as Probed by CO Rotation with Nuclear Magnetic Resonance Relaxation Analysis and Molecular Dynamics Simulations was written by Endo, Takatsugu;Sumida, Hiroki;Fujii, Kaori;Takahashi, Kenji;Kimura, Yoshifumi. And the article was included in Journal of Physical Chemistry B in 2020.Electric Literature of C18H31F6N3O4S2 This article mentions the following:

The rotational dynamics of carbon monoxide (CO) in ionic liquids (ILs) was investigated by NMR relaxation measurements and mol. dynamics (MD) simulations. NMR spin-lattice relaxation time measurements were performed for ¹⁷O-enriched CO in 10 ILs (four imidazolium-cation-based, four phosphonium-cation-based, and two ammonium-cation-based ILs, all paired with the bis(trifluorosulfonylmethane)imide anion). In combination with previously reported data for five ILs and viscosity data, our results indicated that the obtained rotational relaxation times (τ_2R) were much smaller than those predicted using the Stokes-Einstein-Debye (SED) theory. For the same viscosity/temperature values, the τ_2R^-1 value increased linearly with increasing carbon number of the alkyl group in the cation. The deviation from the SED equation was due to the insensitivity of τ_2R to the carbon number, even though a higher carbon number generally leads to higher viscosity values for ILs. To investigate the unique rotational properties of CO in the ILs, MD simulations were performed on five representative ILs (two imidazolium, two phosphonium, and one ammonium) containing CO solutes. From rotational correlation function analyses, the CO rotation mainly occurred in a free rotation-like manner within 1 ps, which explained the relative insensitivity of CO rotation to viscosity. In the subsequent time scale (>1 ps), the minor component of the CO rotation was discriminated among different ILs. It was strongly suggested that, because CO preferably locates in the outer part of the alkyl groups in the cation, the slow CO rotation is correlated with the outer alkyl dynamics, which are decoupled from the whole cation rotation. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Electric Literature of C18H31F6N3O4S2).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. 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.Electric Literature of C18H31F6N3O4S2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Differentiation of 1,4- and 1,5-disubstituted imidazoles was written by Matthews, H. Randall;Rapoport, Henry. And the article was included in Journal of the American Chemical Society in 1973.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

A method is presented for distinguishing 1,4- and 1,5-disubstituted imidazoles by their proton cross-ring coupling constants Other spectral methods also have been evaluated, as well as several methods which have been reported for differentiating such isomers. Comparison of these methods leads to the conclusion that the measurement of cross-ring coupling constants is the most generally satisfactory and reliable procedure. On this basis, structures are assigned to the carboxymethylhistidines, and the histamine metabolite is established as 1-β-d-ribofuranosyl-4- imidazoleacetic acid. 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. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem