Category: imidazoles-derivatives

Photoexcitation dynamics of p-nitroaniline and N,N-dimethyl-p-nitroaniline in 1-alkyl-3-methylimidazolium-cation based ionic liquids with different alkyl-chain lengths was written by Kimura, Y.;Ibaraki, S.;Hirano, R.;Sugita, Y.;Yasaka, Y.;Ueno, M.. And the article was included in Physical Chemistry Chemical Physics in 2017.Formula: C18H31F6N3O4S2 This article mentions the following:

Photoexcitation dynamics of p-nitroaniline (pNA) and N,N-dimethyl-p-nitroaniline (DMpNA) in 1-alkyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([C_nmim][NTf₂]) with different alkyl chain lengths (from C₂ to C₁₂) was investigated using transient absorption spectroscopy. The internal conversion rate from the excited state to the ground state was estimated from bleach recovery around the ground state absorption center, and the successive vibrational cooling rate in the ground state was estimated from the decay of the hot band observed at the red-edge of ground state absorption. The internal conversion rate slightly decreased with an increase in the alkyl-chain length of the cation, while the dependence of DMpNA was more significant than that of pNA. The extent of change was correlated with the change of the reaction free energy and solvent reorganization energy estimated from the absorption spectrum assuming that the internal conversion process is modeled by a back-electron-transfer process. The vibrational cooling rate estimated from the decay of hot-band absorption slightly decreased with an increase in the alkyl-chain length of the cation for both solutes. The hot-band decay of pNA was about 1.5-times faster than that of DMpNA, irresp. of the alkyl-chain length. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Formula: 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Formula: C18H31F6N3O4S2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

New reactive ionic liquids as carriers in polymer inclusion membranes for transport and separation of Cd(II), Cu(II), Pb(II), and Zn(II) ions from chloride aqueous solutions was written by Szczepanski, Piotr;Guo, Haopeng;Dzieszkowski, Krzysztof;Rafinski, Zbigniew;Wolan, Andrzej;Fatyeyeva, Kateryna;Kujawa, Joanna;Kujawski, Wojciech. And the article was included in Journal of Membrane Science in 2021.Application In Synthesis of 1-Octyl-1H-imidazole This article mentions the following:

Three new reactive ionic liquids (RILs) based on the imidazole derivatives were synthesized and used as carriers in polymer inclusion membranes (PIMs) composed of cellulose triacetate (CTA) as a polymer matrix and o-nitrophenyl octyl ether (NPOE) as a plasticizer. The effect of alkyl chain length (C1, C4, and C8) in the imidazolium cation of RILs on the transport and separation properties was evaluated. From among three synthesized RILs only the RIL with the longest alkyl chain (RILC8_Br) can be successfully applied as the carrier for Cd(II) removal from multicomponent aqueous chloride solution containing also Cu(II), Pb(II), and Zn(II) ions. The effects of the stripping phase composition, HCl concentration in the feed solution, and the carrier content in the membrane on the separation performance and transport effectiveness were studied. The results indicate that the RILC8_Br ionic liquid enables selective transport of Cd(II) ions and their active concentration in the stripping solution with the fluxes reaching a value of 2.7 x 10^-10 mol/cm²s. In the investigated feed solution concentration range, the selectivity order was found to be Cd(II) > Zn(II) > Pb(II) ≫ Cu(II) and it was independent of the exptl. conditions. For a description of the transport kinetics a model similar to the first-order reversible reaction equations was applied and its applicability was proved. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Application In Synthesis of 1-Octyl-1H-imidazole).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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.Application In Synthesis of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Enantioselective Hydrogenation of Imidazo[1,2-a]pyridines was written by Schlepphorst, Christoph;Wiesenfeldt, Mario P.;Glorius, Frank. And the article was included in Chemistry – A European Journal in 2018.Reference of 69214-09-1 This article mentions the following:

The enantioselective synthesis of tetrahydroimidazo[1,2-a]pyridines by direct hydrogenation was achieved using a ruthenium/N-heterocyclic carbene (NHC) catalyst. The reaction forgoes the need for protecting or activating groups, proceeds with complete regioselectivity, good to excellent yields, enantiomeric ratios of up to 98:2, and tolerates a broad range of functional groups [e.g., I → II (95.5:4.5 e.r., 99% isolated yield)]. 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridines, which are found in numerous bioactive mols., were directly obtained by this method, and its applicability was demonstrated by the (formal) synthesis of several functional mols. In the experiment, the researchers used many compounds, for example, 5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1Reference of 69214-09-1).

5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Reference of 69214-09-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and conversions of 2-formylbenzimidazoles was written by Dalgatov, D. D.. And the article was included in Sb. Aspirantskikh Rabot, Dagestansk. Univ., Estestv, i Fiz.-Mat. Nauk, Makhachkala in 1964.Recommanded Product: 3012-80-4 This article mentions the following:

Methods for synthesis of 2-formylbenzimidazoles (I) and the N-Me (II) and N-Ph (III) derivatives of I were studied. II was condensed with Me ketones and PhCH₂NO₂ (IV) and I and II were condensed with cyclohexanone (V). 1,2-Bis(2-benzimidazolyl)ethylene glycol (2.94 g.) was dissolved in 100 ml. N HCl, 2.3 g. KIO₄ added, the solution kept 2 days at 20°, and 10% Na₂CO₃ added to alkalinity to yield 93% I, m. 235° (alc.) (decomposition). I (1.46 g.), 7 ml. V, and 7 ml. MeOH was heated at 100°, 5-6 drops 20% KOH added, and the mixture cooled after 10-15 min. to yield 75% the 2-(2-benzimidazolylmethylene) derivative of V, sublimes 175-80° (MeOH). KOH (5.6 g.) and 13.2 g. 2-methylbenzimidazole (VI) in 50 ml. alc. was boiled, 17.2 g. PhSO₃Me added after 1 hr., the mixture heated 2 hrs. and filtered, and the filtrate evaporated to give 10.3 g. l-Me derivative (VIa) of VI, m. 112° (H₂O). Oxidation of VIa with SeO₂ in PhMe at 95° yielded 40% II. 1-Methyl-2-(hydroxymethyl)benzimidazole (1.6 g.) was dissolved in 50 ml. 2N H₂SO₄, 0.05 g. AgNO₃ added, the mixture heated to 70° K₂S₂O₈ added after 4 hrs., the mixture filtered, and the filtrate neutralized with Na₂CO₃ solution to yield 0.4 g. II, m. 110°. II (1.6 g.) and 1.49 g. isonicotinic hydrazide in 8 ml. MeOH was boiled 20 min. to yield 2 g. isonicotinoyl hydrazone of II, m. 200-3° (MeOH). 2-(Hydroxymethyl)benzimidazole (VII) (14.8 g.), 21.2 g. unsaturated leukotrone O, and a concentrated solution of 4 g. NaOH was heated 4 hrs., and Me₂NPh steam distilled to yield 12 g. 1-PhCH₂ derivative of VII, m. 186.5-87° (alc.). To 1.6 g. II and 1.99 g. p-bromoacetophenone (VIII) in 3 ml. MeOH was added 2-3 drops 5% KOH to yield 70% 2-[β-(p-bromobenzoyl)vinyl]-1-methylbenzimidazole, m. 159-60° (alc.). II (1.6 g.) and 3.98 g. VIII were dissolved in 10 ml. hot MeOH, 2 ml. 20% KOH added, and the mixture boiled 1 hr. to yield 74% 1-methyl-2-bis(p-bromo-phenacylmethyl)benzimidazole, m. 186.5-87° (MeOH). Analogously was obtained 2-(β-tolylvinyl)-1-methylbenzimidazole, m. 134° (alc.). II (1.6 g.) and 0.98 g. IV in 5 ml. MeOH and 3 drops 10% KOH was boiled 0.5 hr. to yield 1.7 g. 2-(1-methyl-2-benzimidazolylmethylene) derivative of V, m. 237° (CHCl₃). To 1.37 g. IV in 8 ml. alc. was added 1 g. NaOH in 8 ml. H₂O and in portions 1.6 g. of a solution of II in 10 ml. alc. and after 5 hrs. the mixture neutralized with 1:1 aqueous HCl to yield 73% 2-(β-nitro- α-hydroxy-β-phenylethyl)-1-methylbenzimidazole, m. 162-3° (decomposition) (alc.-Me₂CO). To 20.8 g. 2-methyl-1-phenylbenzimidazole in 200 ml. anhydrous PhMe at 95° was added 11.1 g. SeO₂ over 4 hrs., the mixture heated 2 hrs., the PhMe layer separated and steam distilled, and the residue treated with CHCl₃ to yield 35% III (oil); dinitrophenylhydrazone m. 260-1°; semi-carbazone m. 255-6°. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Recommanded Product: 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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. 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. Recommanded Product: 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Oxa, Thia, Heterocycle, and Carborane Analogues of SQ109: Bacterial and Protozoal Cell Growth Inhibitors was written by Li, Kai;Wang, Yang;Yang, Gyongseon;Byun, Soo Young;Rao, Guodong;Shoen, Carolyn;Yang, Hongliang;Gulati, Anmol;Crick, Dean C.;Cynamon, Michael;Huang, Guozhong;Docampo, Roberto;No, Joo Hwan;Oldfield, Eric. And the article was included in ACS Infectious Diseases in 2015.Formula: C11H20N2 This article mentions the following:

The authors synthesized a library of 48 analogs of the Mycobacterium tuberculosis cell growth inhibitor SQ109 in which the ethylenediamine linker was replaced by oxa, thia, or heterocyclic species, and in some cases, the adamantyl group was replaced by a 1,2-carborane or the N-geranyl group by another hydrophobic species. Compounds were tested against M. tuberculosis (H37Rv and/or Erdman), Mycobacterium smegmatis, Bacillus subtilis, Escherichia coli, Saccharomyces cerevisiae, Trypanosoma brucei, and two human cell lines (human embryonic kidney, HEK293T, and the hepatocellular carcinoma, HepG2). The most potent activity was found against T. brucei, the causative agent of human African trypanosomiasis, and involved targeting of the mitochondrial membrane potential with 15 SQ109 analogs being more active than was SQ109 in cell growth inhibition, having IC₅₀ values as low as 12 nM (5.5 ng/mL) and a selectivity index of ∼300. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Formula: C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 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).Formula: C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers was written by Das, Arko;Joshi, Harshit;Singh, Vinod K.. And the article was included in Organic Letters in 2021.Electric Literature of C6H8N2O This article mentions the following:

An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary-tertiary stereocenters I [R¹ = Ph, CH=CHPh, 2-thienyl, etc.; R² = Me, OMe, OEt, Ph; R³ = 2-pyridyl, benzo[d]thiazol-2-yl] was summarized. The chiral copper(I)-phosphine complex binded with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in α-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields (up to 97%). Furthermore, post-functionalization of the acyl imidazole part had also been demonstrated. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Electric Literature of C6H8N2O).

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.Electric Literature of C6H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A strategy of stabilization via active energy-exchange for bistable electrochromic displays was written by Gu, Chang;Wang, Xiaojun;Jia, Ai-Bo;Zheng, Hongzhi;Zhang, Weiran;Wang, Yuyang;Li, Minjie;Zhang, Yu-Mo;Zhang, Sean Xiao-An. And the article was included in CCS Chemistry in 2022.Computed Properties of C9H15F6N2P This article mentions the following:

As future energy-saving optoelectronics, bistable electrochromic (EC) materials/devices have high energy efficiency for potential applications as smart windows, displays, and information/energy storage, due to their ability to maintain optical states without consuming energy. However, further development is hindered by the lack of in-depth understanding of related key factors and universally applicable design strategies to achieve bistability. Herein, we report a new strategy based on active energyexchange with the aid of proton-coupled electron transfer, which can dynamically adjust the HOMO /LUMO energy levels of materials to obtain good bistability from traditional nonbistable materials. This strategy was thoroughly studied and proven by taking quinone derivatives and bromocresol green derivatives as examples. The device obtained after further polymerization and optimization showed remarkable bistability, coloration efficiency, and application potential for energy-saving flexible displays. The success, challenges, and cognitive gains of this strategy not only accelerate the development of various energysaving optoelectronic materials/devices, but are also likely to stimulate progress in physics, chem., and materials. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9Computed Properties of C9H15F6N2P).

1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Computed Properties of C9H15F6N2P

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Anions as Dynamic Probes for Ionic Liquid Mixtures was written by Di Pietro, Maria Enrica;Castiglione, Franca;Mele, Andrea. And the article was included in Journal of Physical Chemistry B in 2020.Reference of 404001-48-5 This article mentions the following:

Ionic liquid (IL) mixtures were proposed as a viable alternative to rationally fine-tune the physicochem. properties of ILs for a variety of applications. The understanding of the effects of mixing ILs on the properties of the mixtures is however only in the early stages. Two series of ionic liquid mixtures, based on the 1-ethyl-3-methylimidazolium and 1-dodecyl-3-methylimidazolium cations, and having a common anion (tetrafluoroborate or bis(trifluoromethylsulfonyl)imide), were prepared and deeply characterized via multiple NMR techniques. Diffusion and relaxation methods combined with 2D ion-ion correlation (nuclear Overhauser enhancement) experiments were used for a better understanding of the interplay between dynamics and structure of IL mixtures A crucial role of the anion in driving the mixture’s behavior emerged, making them important “dynamic probes” for gaining information of the polar and nonpolar regions of ionic liquids and their mixtures In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Reference of 404001-48-5).

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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Reference of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Cocrystal formation by ionic liquid-assisted grinding: case study with cocrystals of caffeine was written by Mukherjee, Arijit;Rogers, Robin D.;Myerson, A. S.. And the article was included in CrystEngComm in 2018.Product Details of 404001-48-5 This article mentions the following:

Liquid assisted grinding using imidazolium-based ionic liquids (IL-AG) was found to be effective in isolation of cocrystals and cocrystal polymorphs. Isolation of specific polymorphs of caffeine-citric acid (CAF-CA) and caffeine-glutaric acid (CAF-GLU) cocrystals highlights the tunability of ILs in polymorphic control. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Product Details of 404001-48-5).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Product Details of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of [¹⁸F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)acetamide], a marker for PET detection of hypoxia was written by Josse, Olivier;Labar, Daniel;Georges, Benoit;Gregoire, Vincent;Marchand-Brynaert, Jacqueline. And the article was included in Bioorganic & Medicinal Chemistry in 2001.Application of 22813-32-7 This article mentions the following:

[¹⁸F]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)acetamide ([¹⁸F]-EF3) has been prepared in 65% chem. yield and 5% radiochem. yield by coupling 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl)acetate with [¹⁸F]-3,3,3-trifluoropropylamine. This original radiolabeled key synthon was obtained in 40% overall chem. yield by oxidative [¹⁸F]-fluorodesulfurization of Et N-phthalimido-3-aminopropanedithioate, followed by deprotection with hydrazine of the resulting [¹⁸F]-N-phthalimido-3,3,3-trifluoropropylamine. The process was performed within 90 min, from the [¹⁸F]-HF production in the cyclotron to the purification of the final target. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Application of 22813-32-7).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) 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. 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. Application of 22813-32-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem