Imidazoles-derivatives

COSMO-SAC molecular screening method to analyze imidazole ionic liquids for toluene vapor absorption was written by Zhang, Wenlin;Yan, Jiawei;Sun, Tengfei;Zhang, Bin;Lan, Xiaoyan;Li, Chunli. And the article was included in Huagong Xuebao (Chinese Edition) in 2018.HPLC of Formula: 404001-48-5 This article mentions the following:

Imidazolium ionic liquids as toluene vapor absorbent were evaluated by a mol. screening method based on the COSMO-SAC model. A σ-map was established for hundred common imidazolium ionic liquids composed of N,N′-dialkylimidazolium cation and an anion. Absorption potential of ionic liquids to toluene vapor at 303.15 K was calculated from the σ-map and was used as thermodn. evaluation criterion to screen absorbents. Exptl. measurements on saturated absorption of toluene vapor in six ionic liquids showed consistent results with these of mol. screening, which verified reliability of this mol. screening method. Interaction energy of ionic liquid cation and toluene was calculated by Gaussian 09 software. Subsequently, effects of kinetic factors such as vapor inlet concentration and velocity were explored. An initial toluene absorption by ionic liquid reached to 96.2% under temperature of 303.15 K, inlet concentration of 10000 mg · m^-3, and inlet velocity of 0.05 m³ · h^-1. Further study indicated that toluene absorption was almost not changed with increasing number of repeated use cycles of ionic liquid absorbents. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5HPLC of Formula: 404001-48-5).

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–C6) is higher than in water and generally decreases with a 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. HPLC of Formula: 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Color reactions of 2,6-dichloroquinone chloroimide with derivatives of glyoxaline-2-thiol was written by Searle, C. E.. And the article was included in Journal of Applied Chemistry in 1955.Synthetic Route of C6H8N2O2S This article mentions the following:

A large number of glyoxaline-2-thiols and some 2-alkylthioglyoxalines react with 2,6-dichloroquinone chloroimide at pH 8 to give colored products which are in most cases soluble in CHCl₃. In the experiment, the researchers used many compounds, for example, Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8Synthetic Route of C6H8N2O2S).

Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Synthetic Route of C6H8N2O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Theoretical elucidation of the multi-functional synthetic methodology for switchable Ni(0)-catalyzed C-H allylations, alkenylations and dienylations with allenes was written by Liu, Yuxia;Wang, Kaifeng;Ling, Baoping;Chen, Guang;Li, Yulin;Liu, Lingjun;Bi, Siwei. And the article was included in Catalysis Science & Technology in 2020.Quality Control of 1-Methylbenzimidazole This article mentions the following:

The Ni(0)-catalyzed coupling of benzimidazole with 1,1-disubstituted allenes represents a new strategy for achieving controllable C-H allylations, alkenylations and dienylations. To understand the detailed mechanisms and origins of the switchable selectivities, d. functional theory (DFT) calculations were conducted. The results using a tBu-substituted allene demonstrate that the formation of the allylated product involves a Ni-catalyzed C-H activation mechanism through ligand-to-ligand-hydrogen transfer (LLHT) under base-free conditions. In contrast, a Ni/NaOtBu co-promoted C-H activation mechanism is newly proposed in the presence of NaOtBu, which is remarkably different from the previously reported literature. The novel mechanism emphasizes that NaOtBu abstracts the Ni-activated heterocyclic (ipso-C)H atom followed by turnover limiting Ni slippage, and subsequently the allylated product is generated after alkene insertion and protonation. The strong electrostatic attraction between Ni and heterocyclic ipso-C in the Ni slippage pre-intermediate is critical for facilitating the Ni slippage. Once formed, the allylated product, assisted by NaOtBu, further evolves into a more stable alkenylated isomer. Employing a (tert-butyldimethylsilyl)-ether substituted allene as the substrate, the NaOtBu-induced chemoselectivity for dienylation vs. alkenylation was also probed and it was found that the O(tBu)-H···O(Si) hydrogen bonding interaction in the C-O(Si) cleavage pre-intermediate remarkably weakens the adjacent C-O(Si) σ-bond, thereby resulting in an exclusive C-O(Si) cleaved dienylation product. Further theor. predictions suggest that the chemoselectivity might be reversed by replacing tBu in NaOtBu by the withdrawing C(CF₃)₃ group. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Quality Control of 1-Methylbenzimidazole).

1-Methylbenzimidazole (cas: 1632-83-3) 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.Quality Control of 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Versatile and Scalable Method for Producing N-Functionalized Imidazoles was written by Bara, Jason E.. And the article was included in Industrial & Engineering Chemistry Research in 2011.Reference of 21252-69-7 This article mentions the following:

A method for producing sodium imidazolate (NaIm) at a scale of ∼400 g from only commodity starting materials has been developed. The NaIm product was then utilized as a starting material to produce 20 different N-functionalized imidazole and bis(imidazole) compounds, with the application of a common procedure involving minimal solvent volumes and straightforward purification via flash chromatog. and solvent evaporation Generating N-functionalized imidazoles “on demand” from NaIm and alkyl halides (or similar compounds) can eliminate the need for hazardous starting materials such as NaH and anhydrous solvents that have typically been employed in their synthesis. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Reference of 21252-69-7).

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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Reference of 21252-69-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline was written by Casagrande, Manolo;Barteselli, Anna;Basilico, Nicoletta;Parapini, Silvia;Taramelli, Donatella;Sparatore, Anna. And the article was included in Bioorganic & Medicinal Chemistry in 2012.Application of 22600-77-7 This article mentions the following:

With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-4-(heteroarylmethylamino)quinoline and 7-chloro-4-(heteroarylamino)quinoline derivatives was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent mols. inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC₅₀ < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. In the experiment, the researchers used many compounds, for example, (1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7Application of 22600-77-7).

(1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Application of 22600-77-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and pharmacological activity of amides of 2,3-dihydroimidazo- and 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazolyl-N-acetic acids was written by Anisimova, V. A.;Spasov, A. A.;Kosolapov, V. A.;Tolpygin, I. E.;Tibir’kova, E. V.;Salaznikova, O. A.;Kuznetsova, V. A.;Gurova, N. A.;Lenskaya, K. V.;Yakovlev, D. S.;Mal’tsev, D. V.;Kolobrodova, N. A.;Mitina, T. M.;Grechko, O. Yu.. And the article was included in Pharmaceutical Chemistry Journal in 2013.Category: imidazoles-derivatives This article mentions the following:

A series of amides of 2,3-dihydroimidazo- and 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazolyl-N-acetic acids were synthesized. Their pharmacol. activity was studied. It was established that the synthesized substances possessed antiaggregant properties and antiarrhythmic activity. Some of these amides exhibited antioxidant and hypoglycemic effects in addition to antagonist activity with respect to serotonin 5-HT₂ and purine P2Y₁ receptors. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Category: imidazoles-derivatives).

2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Compatibility of supported ionic liquid phase catalysts under ultrasonication was written by Jagadale, Megha;Kale, Dolly;Salunkhe, Rajashri;Rajmane, Mohan;Rashinkar, Gajanan. And the article was included in Journal of Molecular Liquids in 2018.Formula: C4H7ClN2 This article mentions the following:

Various supported ionic liquid phase (SILP) catalysts containing hexafluorophosphate anion was prepared by covalent grafting of imidazolium ionic liquid in the matrix of cellulose, silica and Merrifield resin followed by anion metathesis reaction. The compatibility of SILP catalysts in the synthesis of 1,4-dihydropyridines under ultrasonication was investigated. The results revealed that SILP catalysts was effectively used under ultrasonication without phys., chem. and structural changes as evidenced from various anal. techniques. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Formula: C4H7ClN2).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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. 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. Formula: C4H7ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Phosphorescent Ruthenium Complexes with a Nitroimidazole Unit that Image Oxygen Fluctuation in Tumor Tissue was written by Son, Aoi;Kawasaki, Atsushi;Hara, Daiki;Ito, Takeo;Tanabe, Kazuhito. And the article was included in Chemistry – A European Journal in 2015.Safety of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:

Understanding oxygen fluctuation in a cancerous tumor is important for effective treatment, especially during radiotherapy. Ruthenium complexes bearing a nitroimidazole group report the oxygen status in tumor tissue directly. The nitroimidazole group was known to be accumulated in hypoxic tumor tissues. However, the ruthenium complex showed strong phosphorescence around 600 nm. The emission of ruthenium is quenched instantaneously by mol. oxygen due to energy transfer between triplet states of oxygen and ruthenium complex, but the emission is then recovered by the removal of oxygen. Thus, the authors could observe oxygen fluctuation in tumor tissue in a real-time manner by monitoring the phosphorescence of the ruthenium complex. The versatility of the probe is demonstrated by monitoring oxygen fluctuation in living cells and tumor tissue planted in mice. The ruthenium complex promptly penetrated plasma membrane and accumulated in cells to emit its oxygen-dependent phosphorescence. In vivo experiments revealed that the oxygen level in tumor tissue seems to fluctuate at the sub-minute timescale. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Safety of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Tertiary amine oxides. XVIII. The reduction of 1-[(1-oxido-2-pyridyl)methyl]pyridinium salt was written by Hamana, Masatomo;Umezawa, Bunsuke;Noda, Kanji. And the article was included in Chemical & Pharmaceutical Bulletin in 1963.COA of Formula: C9H8N2O This article mentions the following:

By a modified King reaction, 2-picoline 1-oxide (I), C₅H₅N, and iodine in the molar ratio 1:2:1 refluxed 5 hrs. in dioxane gave 16% title compound (II) (X = I), m. 180-1° (decomposition). Change of solvent to xylene in the same procedure yielded unexpectedly 5% pyrido[1′,2′:3,4]imidazo[1,g-a]pyridinium salt (III) (X = I), m. 252-3°; picrate m. 217-18°. The structure of III was confirmed by a 2nd synthesis, whereby 2-(BrCH₂)C₅H₄N and 2-BrC₅H₄N were refluxed 20 hrs. in MeCN to effect cyclization and to yield, after chromatography over Al₂O₃-Celite (2:1), 18% III (X = Br), m. 150-2°, converted to III (X = I) in 100% yield by refluxing 4 hrs. with NaI in Me₂CO. The identity of the 2 samples of III (X = I) was established by both infrared and ultraviolet absorption spectra (curves shown). Refluxing II 5 hrs. in xylene, or with C₅H₅N.HI in xylene, or with iodine in xylene gave III in, resp., a small amount, 64%, and 53% yields. However, refluxing 1-(2-pyridylmethyl)pyridinium bromide (IV) 5 hrs. with C₅H₅N.HI in xylene left only unchanged IV; picrate m. 169-70°. This result indicated the essential role of the N-oxide group of H in the formation of III. Chromatography on Amberlite IRA-400 (Cl^– or HO^– type) effected the anion exchange in II (from X = I to X = Cl or HO). The selective reduction of either the N-oxide or the pyridinium group of II was studied under varied conditions. Catalytic hydrogenation (Raney Ni) of II (X = Cl) in MeOH or 4% AcOH, after absorption of 1 molar equivalent H, yielded, resp., 43 or 41% IV, and after absorption of 4 molar equivalents H, 74 or 91% N-(2-pyridylmethyl)piperidine (V), b₄ 100-15°; picrate m. 180-2°. Thus, Raney Ni was specific for the N-oxide rather than for the pyridinium reduction Catalytic hydrogenation (Raney Ni) of II (X = HO) after absorption of 4 molar equivalents H yielded (in MeOH solution) 71% V, and (in 1% NaOH solution) 91% V. II (X = Cl) catalytically reduced with Pd-C in acid medium also gave IV in 68% yield, whereas in neutral medium, Pd-C selectively reduced the pyridinium group of 2-[(1,2,3,6-tetrahydro-1-pyridyl)methyl]pyridine 1-oxide (VI) to yield 6.3% V and 40% 2-piperidinomethylpyridine 1-oxide (VII); picrate m. 132-3°. VI, picrate m. 115-16°, was prepared in 92% yield by reducing II (X = I) with NaBH₄ at room temperature, and VI was deoxygenated by adding PCl₃ in CHCl₃ under ice cooling and refluxing the mixture 30 min. on a water bath to yield 34% 1-(2-pyridylmethyl)-l,2,3,6-tetrahydropyridine (VIII), b₄ 106-11° (picrate m. 171-2°), prepared also in 63% yield by warming 2-(BrCH₂)C₅H₄N.HBr 30 min. with Δ³-piperidine-HCl and K₂CO₃ on a water bath. Similarly, refluxing free 2-(BrCH₂)C₅H₄N with piperidine in EtOH 1 hr., evaporating the solvent, and making the residue alk. with K₂CO₃ yielded 100% V. VII, m. 93 5°, was prepared in 10% yield by refluxing 2-(BrCH₂)C₅H₄NO 3 hrs. with piperidine in EtOH, and this, as was VI, was deoxygenated with PCl₃ in CHCl₃ to yield 48% V. VI and VIII sep. catalytically hydrogenated (Raney Ni) yielded, resp., 17% and 95% V. II, reduced by warming 3.5 hrs. at 60° with Zn dust and AcOH, was cleaved to yield 58% 2-picoline (picrate m. 164-5°) and 51% C₅H₅N (picrate m. 165-7°). In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4COA of Formula: C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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.COA of Formula: C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A quantum mechanical study of alkylimidazolium halide ionic liquids was written by Li, Wei;Qi, Chuansong;Rong, Hua;Wu, Xinmin;Gong, Liangfa. And the article was included in Chemical Physics Letters in 2012.Safety of 1-Methyl-3-propylimidazolium Chloride This article mentions the following:

Thirty imidazolium (IM) halide compounds were studied using DFT methods (B3LYP, B3P86, and PBE1PBE1) methods. Geometry optimization and interaction energy calculations were performed using the B3LYP/6-311++G(d,p) method for ions composed of one alkylimidazolium cation and two or three halogen anions. The obtained structures were consistent with exptl. results. In addition, a linear correlation between m.ps. and interaction energies was obtained for the compounds studied, and this relationship was consistent with that obtained for amino acid cation based ionic liquids In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Safety of 1-Methyl-3-propylimidazolium Chloride).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) 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.Safety of 1-Methyl-3-propylimidazolium Chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem