Category: imidazoles-derivatives

The Fairy Chemical Imidazole-4-carboxamide Inhibits the Expression of Axl, PD-L1, and PD-L2 and Improves Response to Cisplatin in Melanoma was written by Inoue, Chisa;Yasuma, Taro;D’Alessandro-Gabazza, Corina N.;Toda, Masaaki;Fridman D’Alessandro, Valeria;Inoue, Ryo;Fujimoto, Hajime;Kobori, Hajime;Tharavecharak, Suphachai;Takeshita, Atsuro;Nishihama, Kota;Okano, Yuko;Wu, Jing;Kobayashi, Tetsu;Yano, Yutaka;Kawagishi, Hirokazu;Gabazza, Esteban C.. And the article was included in Cells in 2022.Application In Synthesis of 1H-Imidazole-4-carboxamide This article mentions the following:

The leading cause of death worldwide is cancer. Many reports have proved the beneficial effect of mushrooms in cancer. However, the precise mechanism is not completely clear. In the present study, we focused on the medicinal properties of biomols. released by fairy ring-forming mushrooms. Fairy chems. generally stimulate or inhibit the growth of surrounding vegetation. In the present study, we evaluated whether fairy chems. (2-azahypoxanthine, 2-aza-8-oxohypoxanthine, and imidazole-4-carboxamide) exert anticancer activity by decreasing the expression of Axl and immune checkpoint mols. in melanoma cells. We used B16F10 melanoma cell lines and a melanoma xenograft model in the experiments Treatment of melanoma xenograft with cisplatin combined with imidazole-4-carboxamide significantly decreased the tumor volume compared to untreated mice or mice treated cisplatin alone. In addition, mice treated with cisplatin and imidazole-4-carboxamide showed increased peritumoral infiltration of T cells compared to mice treated with cisplatin alone. In vitro studies showed that all fairy chems., including imidazole-4-carboxamide, inhibit the expression of immune checkpoint mols. and Axl compared to controls. Imidazole-4-carboxamide also significantly blocks the cisplatin-induced upregulation of PD-L1. These observations point to the fairy chem. imidazole-4-carboxamide as a promising coadjuvant therapy with cisplatin in patients with cancer. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Application In Synthesis of 1H-Imidazole-4-carboxamide).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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 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.Application In Synthesis of 1H-Imidazole-4-carboxamide

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

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

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

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

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

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

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

Acylation of benzimidazole by the Regel-Buechel method. 2. Deacylation and dissociation of 1-methyl-3-acyl-2-(1-methyl-2-benzimidazolyl)benzimidazolin-4-ones was written by Khristich, B. I.;Bondarenko, E. V.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1987.Application of 3012-80-4 This article mentions the following:

1-Methyl-3-acyl-2-(1-methylbenzimidazol-2-yl)-2-benzimidazolines with an excess of acyl halide are transformed to unstable 1-methyl-3-acyl-2-(1-methyl-3-acyl-2-benzimidazolin-2-yl)benzimidazolium chlorides, which undergo intramol. oxidation-reduction-decomposition to give 1,1′-dimethyl-2,2′-bibenzimidazolyl and aldehyde, and dissociates at the C-C bond connecting the benzimidazole and benzimidazoline fragments to a carbene-ylide and 1-methyl-3-acylbenzimidazolium chloride. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Application of 3012-80-4).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Understanding Cellulose Dissolution: Energetics of Interactions of Ionic Liquids and Cellobiose Revealed by Solution Microcalorimetry was written by Nunes de Oliveira, Heitor Fernando;Rinaldi, Roberto. And the article was included in ChemSusChem in 2015.Application In Synthesis of 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

In this report, the interactions between fifteen selected ionic liquids (ILs) and cellobiose (CB) were examined by high-precision solution microcalorimetry. The heat of mixing (Δ_mixH) of CB and ILs, or CB and IL/mol. solvent (MS) solutions, provides the first ever-published measure of the affinity of CB with ILs. Most importantly, we found that there is a very good correlation between the nature of the results found for Δ_mixH_(CB) and the solubility behavior of cellulose. This correlation suggests that Δ_mixH_(CB) offers a good estimate of the enthalpy of dissolution of cellulose even in solvents in which cellulose is insoluble Therefore, the current findings open up new horizons for unravelling the intricacies of the thermodn. factors accounting for the spontaneity of cellulose dissolution in ILs or IL/MS solutions In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Application In Synthesis of 1-Methyl-1H-imidazol-3-ium chloride).

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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Application In Synthesis of 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem