Imidazoles-derivatives

Chemistry of antipernicious anemia factors. III. 5,6-Disubstituted benzimidazoles as products of acid hydrolysis of vitamin B₁₂ was written by Beaven, G. R.;Holiday, E. R.;Johnson, E. A.;Ellis, B.;Mamalis, P.;Petrow, V.;Sturgeon, B.. And the article was included in Journal of Pharmacy and Pharmacology in 1949.Safety of 7-Methyl-1H-benzo[d]imidazole This article mentions the following:

N-(p-Tolylsulfonyl)-nitroanilides are prepared from the nitro amine in pyridine treated portionwise with p-MeC₆H₄SO₂Cl, then heated at 100° for 2 h., acidified, and crystallized Yields are 80-95%. The following 2′-nitro-p-toluenesulfonanilides are prepd: 4′-Me (I), yellow needles from alc., m. 104°; 6′-Me (II), yellow prisms from alc., m. 125°; 3′,4′-di-Me (III), prismatic needles from alc., m. 126-7°; 4′,5′-di-Me (IV), yellow blades from alc., m. 149-50°. The sulfonanilides are methylated by refluxing with Me₂SO₄ in alk. medium; yields, 80-95%. I yields 2′-nitro-N,4′-dimethyl-p-toluenesulfonanilide, pale yellow prisms, m. 128°. The methylated product from II forms silvery leaflets, m. 139-40°; from III, colorless prisms, m. 137°; from IV, m. 125-7°. Mixtures of the N-methyl-p-toluenesulfonanilides, AcOH, and H₂SO₄ are heated at 100° for 1-2 h. and poured into ice and the hydrolyzed amine recrystallized from alc.; yield, 60-75%. The corresponding 2-nitroanilines are: N,3,4-tri-Me, scarlet prisms with 0.5 H₂O, m. 59-60°; N,4,5-tri-Me, resublimed at 0.05 mm. and 100°, orange-red needles, m. 138°. Preparation of benzimidazoles: Shake the nitro amine in EtOH with H (10% Pd-C catalyst), remove the catalyst, dry the solution under N, dissolve the residue in 4 N HCl, add the appropriate aliphatic acid, reflux in N, precipitate with NH₃, and recrystallize; yields, 50-60%. The benzimidazoles prepared are: 1-Me, needles [from light petroleum (V)], m. 64°; 2-Me, needles from H₂O, m. 176°; 4-Me, needles from AcOEt-V, m. 140°; 5-Me, needles from AcOEt-V, m. 113°, b_0.1 169-72°; 1,2-di-Me, needles from AcOEt-V, m. 109-10°; 1,5-di-Me, needles from AcOEt-V, m. 94°; 1,6-di-Me, needles from V, m. 74-5°; 1,7-di-Me, prismatic needles from AcOEt-V, m. 68-70.5°; 2,4-di-Me, prisms from AcOEt, m. 168-9 °; 2,5-di-Me, leaflets from AcOEt-V, m. 202°; 4,5-di-Me, leaflets from aqueous alc., m. 196-7°; 5,6-di-Me, needles from AcOEt-V, m. 199-200°; 1,2,5-tri-Me, plates from AcOEt, m. 141°; 1,2,6-tri-Me, rods from AcOEt-V, m. 119-20 °; 1,2,7-tri-Me, fine needles from V, m. 146-7°; 1,4,5-tri-Me, white needles from V, m. 95-6°; 2,4,5-tri-Me, needles from aqueous alc., m. 188-90°; 1,5,6-tri-Me, needles from AcOEt-V, m. 142-3°; 2,5,6-tri-Me, needles from aqueous alc., m. 233-4°; 1,2,4,5-tetra-Me, long needles from aqueous alc., m. 144-5°; 1,2,5,6-tetra-Me, pale yellow prisms from AcOEt-V, m. 164°. The methylated benzimidazoles are compared spectroscopically with 3 chem. related components, α, β, and γ, separated from the “285 component” by chromatog. The α- and β-components are identified as 1-substituted 5,6-dimethylbenzimidazoles, and γ is 5,6-dimethylbenzimidazole (VI). Only one VI residue is released from vitamin B₁₂ on acid hydrolysis; the benzimidazole nucleus exists preformed in the vitamin, and components α, β, and γ represent successive stages of degradation of a common precursor. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Safety of 7-Methyl-1H-benzo[d]imidazole).

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Safety of 7-Methyl-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Development of Selective Clk1 and -4 Inhibitors for Cellular Depletion of Cancer-Relevant Proteins was written by ElHady, Ahmed K.;Abdel-Halim, Mohammad;Abadi, Ashraf H.;Engel, Matthias. And the article was included in Journal of Medicinal Chemistry in 2017.Category: imidazoles-derivatives This article mentions the following:

In cancer cells, kinases of the Clk family control the supply of full-length, functional mRNAs coding for a variety of proteins essential to cell growth and survival. Thus, inhibition of Clks might become a novel anticancer strategy, leading to a selective depletion of cancer-relevant proteins after turnover. On the basis of a Weinreb amide hit compound, the authors designed and synthesized a diverse set of methoxybenzothiophene-2-carboxamides, of which the N-benzylated derivative showed enhanced Clk1 inhibitory activity. Introduction of a m-fluorine in the benzyl moiety eventually led to the discovery of compound 21b (5-methoxybenzo[b]thiophene-2-carboxylic acid (3-fluorobenzyl)methylamide), a potent inhibitor of Clk1 and -4 (IC₅₀ = 7 and 2.3 nM, resp.), exhibiting an unprecedented selectivity over Dyrk1A. Compound 21b triggered the depletion of EGFR, HDAC1, and p70S6 kinase from the cancer cells, with potencies in line with the measured GIC₅₀ values. In contrast, the cellular effects of congener 21a (5-methoxybenzo[b]thiophene-2-carboxylic acid 3-fluorobenzylamide), which inhibited Clk1 only weakly, were substantially lower. In the experiment, the researchers used many compounds, for example, (1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7Category: imidazoles-derivatives).

(1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7) 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 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

Materially Engineered Artificial Pollinators was written by Chechetka, Svetlana A.;Yu, Yue;Tange, Masayoshi;Miyako, Eijiro. And the article was included in Chem in 2017.Electric Literature of C9H15F6N2P This article mentions the following:

Pollinating insects such as honeybees play a critical role in maintaining the natural environment. The decline in honeybee populations is a global issue with significant repercussions with respect to the pollination of plants. The simultaneous expression of multifunctionality from synthesized ionic liquid gels (ILGs) for biotechnol. is presented in this study. We also demonstrate that, when mixed with photochromic organic compounds, ILGs display rapid color changes, similar to light-triggered camouflage, on living Musca domestica specimens. By further exploiting the physicochem. properties of ILGs, we were able to achieve effective pollen adsorption by ILG-functionalized Formica japonica specimens from Tulipa gesneriana flowers with high biocompatibility. In addition, a radiowave-controllable bio-inspired flying robot equipped with ILG-coated vertically aligned animal hairs could be used to successfully pollinate Lilium japonicum flowers. Such materially engineered artificial plant pollinators should lead to the development of high-performance robotics that can help counter the decline in honeybee populations. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9Electric Literature 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.Electric Literature of C9H15F6N2P

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of the anti-hypertensive drug olmesartan medoxomil in greener approach was written by Shanker, Ch. Gouri;Sujitha, D.;Kumar, D. Aravind;Sudhakar, K.. And the article was included in Heterocyclic Letters in 2018.Reference of 145040-37-5 This article mentions the following:

Proton and metal ion-exchanged Montmorillonite and Copper-Aluminum Hydroxyapatite (Cu-HAP) catalysts were effectively used in the esterifiaction, C-N bond formation and Detritylation in methanol efford Olmesartan Medoxomil in good yields. The catalysts were quant. recovered from reaction mixture by simple filtration and reused for four cycles with consistent activity. 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: 145040-37-5Reference of 145040-37-5).

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. 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 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.Reference of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electrochemical reduction of bifunctional organic compounds. XI. Substituted N-methylnitroimidazoles was written by Kargin, Yu. M.;Latypova, V. Z.;Fassakhov, R. Kh.;Arkhipov, A. I.;Eneikina, T. A.;Sharnin, G. P.. And the article was included in Zhurnal Obshchei Khimii in 1979.Synthetic Route of C4H5N3O2 This article mentions the following:

The mechanism was studied of the electrochem. reduction of nitro- and halo-substituted N-methylimidazoles where the substituents are NO₂, Cl, Br, H, and NHPh. The process begins with the reverse transfer of an electron to the mol. to form anion radicals with different degrees of stability. The rate of anionic elimination of Br^– from positions 2 and 5 in the anion radicals of 1-methyl-2(5)-bromo-4-nitroimidazole (k = 8.2 ± 0.5 and 12.1 ± 0.5 s^-1, resp.) was evaluated. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Synthetic Route of C4H5N3O2).

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. 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. Synthetic Route of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts was written by Taylor, Dominic;Malcomson, Thomas;Zhakeyev, Adilet;Cheng, Shengxian;Rosair, Georgina M.;Marques-Hueso, Jose;Xu, Zhengtao;Paterson, Martin J.;Dalgarno, Scott J.;Vilela, Filipe. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 1632-83-3 This article mentions the following:

The synthesis, characterization, and application of a library of 26 D-A compounds I (R = Ph, 4-hydroxyphenyl, thiophen-2-yl, etc.) based on the BTZ group were described. By varying the donor groups while keeping the BTZ acceptor group the same, and the photocatalyst’s optoelectronic and photophys. properties can be systematically modified. These photocatalysts were then validated using a Minisci-type decarboxylative alkylation of electron deficient heteroarenes (such as lepidine, 2-methylquinoline, isoquinoline, etc.) as a test reaction under both batch and continuous flow conditions. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Related Products of 1632-83-3).

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. 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. Related Products of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Highly efficient protocol for the aromatic compounds nitration catalyzed by magnetically recyclable core/shell nanocomposite was written by Maleki, Ali;Aghaei, Morteza;Paydar, Reza. And the article was included in Journal of the Iranian Chemical Society in 2017.HPLC of Formula: 3034-41-1 This article mentions the following:

An efficient protocol for the nitration of aromatic compounds in the presence of a catalytic amount of sulfuric acid-functionalized silica-based magnetic core/shell nanocomposite was reported. The designed products were obtained in high yields in relatively short reaction times at room temperature under solvent-free conditions. The nanocatalyst was simply recovered from the reaction mixture by using an external magnet and efficiently reused for several times. The characterization of particle size, morphol. and elemental anal. of the nanocatalyst were provided by SEM, transmission electron microscopy and energy-dispersive X-ray spectroscopy analyses, resp. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1HPLC of Formula: 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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.HPLC of Formula: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Activity of antitumor drugs against african trypanosomes was written by Kinnamon, Kenneth E.;Steck, Edgar A.;Rane, Dora S.. And the article was included in Antimicrobial Agents and Chemotherapy in 1979.Recommanded Product: 26832-08-6 This article mentions the following:

Of 49 compounds with antitumor properties, 6 had significant activity against Trypanosoma rhodesiense infections in mice. In order of decreasing activity these compounds were imidazole-4-carboxamide (I) [26832-08-6], inosine diglycoaldehyde (II) [23590-99-0], cis-diamminedichloroplatinum [15663-27-1], streptozotocin [18883-66-4], coralyne sulfate [38989-37-6], and 5-fluoro-2′-deoxyuridine [50-91-9]. Of these compounds, only diamminedichloroplatinum was toxic. These compounds may have therapeutic importance against Trypanosoma infections. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Recommanded Product: 26832-08-6).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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.Recommanded Product: 26832-08-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Protic, Aprotic, and Choline-Derived Ionic Liquids: Toward Enhancing the Accessibility of Hardwood and Softwood was written by Rigual, Victoria;Ovejero-Perez, Antonio;Rivas, Sandra;Dominguez, Juan C.;Alonso, M. Virginia;Oliet, Mercedes;Rodriguez, Francisco. And the article was included in ACS Sustainable Chemistry & Engineering in 2020.Reference of 35487-17-3 This article mentions the following:

A side-by-side comparison of softwood (pine) vs. hardwood (eucalyptus) pretreatment using 3 protic, 3 aprotic, and 3 choline-derived ionic liquids (ILs) is proposed. While the protic ionic liquid 2-hydroxyethylammonium formate leads to alkali lignin dissolution at 30°C after 1 h, the lack of interactions with the whole-cell wall limits the biomass disruption. On the contrary, the protic ionic liquid 1-methylimidazolium chloride produces a catalytic effect that extracts almost all of the hemicelluloses, and partially the lignin. Remarkable digestibilities are obtained with choline acetate ([Ch][OAc]) in eucalyptus (69%), while in pine, protic, and choline-derived ILs tested do not appear to be real “greener” alternatives to conventional ILs such as 1-ethyl-3-methylimidazolium acetate (the highest digestibility, 84%). Solid morphol. revealed a smoother surface in pine pretreated with [Mim][Cl], and confocal fluorescence microscopy was used to distinguish surface holocellulose and lignin, highlighting differences in the accessibility of hardwood vs. softwood due to the presence of surface lignin. Two-dimensional NMR spectroscopy of saccharified samples pretreated with [Ch][OAc] showed the presence of groups derived from acetate. Finally, thermogravimetric anal. and spectroscopy techniques reveal the difficulties in recovering the ionic liquid and conclude a work that describes the strengths and weaknesses of the ILs and biomasses studied. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Reference of 35487-17-3).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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. 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. Reference of 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A simple, eco-friendly, and recyclable bi-functional acidic ionic liquid catalysts for Beckmann rearrangement was written by Kore, Rajkumar;Srivastava, Rajendra. And the article was included in Journal of Molecular Catalysis A: Chemical in 2013.Synthetic Route of C4H7ClN2 This article mentions the following:

A library of ionic liquids was prepared by varying the cations and anions. Bi-functional acidic ionic liquids were prepared by the direct combination of ionic liquids and ZnCl₂. Ionic liquids were investigated in the Beckmann rearrangements. A simple, eco-friendly, and recyclable bi-functional acidic ionic liquid based protocol for Beckmann rearrangement is developed, which is based on the fine tuning of the Broensted and the Lewis acidity of ionic liquids In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Synthetic Route of C4H7ClN2).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem