Category: imidazoles-derivatives

Reactions of 4-halo- and 4-methylthio-imidazolium salts with sulfide and methanethiolate ions was written by Begtrup, Mikael. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1979.Application In Synthesis of 4-Bromo-1-methylimidazole This article mentions the following:

The chloroimidazolium salts I [R = H (II), Ph, R¹ = Cl, X = 4-MeC₆H₄SO₃] reacted with Na₂S-NaH to give the ring cleaved products MeNHC(S)CH₂NMeCOR (III; R = H, Ph) and with MeSH-NaH to give the substituted products I [R = H (IV), Ph, R¹ = SMe, X = Cl]; further treatment of IV with MeSH-NaH gave the thione V (R = SMe) and after treatment with NaBr, I (R = R¹ = H, X = Br). The bromo analog I (R = H, R¹ = Br, X = 4-MeC₆H₄SO₃) (VI) reacted with excess Na₂S-NaH to give 67% V (R = H) and with 1 mol equiv to give 42% I (R = R¹ = H, X = Br), together with V (R = H) and III (R = H); similar treatment of I (R = Ph, R¹ = Br, X = 4-MeC₆H₄SO₃) gave 77% I (R = Ph, R¹ = H, X = Br). In the Cl series, thiation predominated over ring cleavage, V (R = Cl) being formed when II was treated with Na₂S-S. When VI was subjected to similar treatment, reduction with formation of I (R = R¹ = H, X = Br) and V (R = H) prevailed over thiation to V (R = Br). Treatment of VI with MeSH-NaH (1 mol equiv) gave 82% I (R = R¹ = H, X = Br) whereas with excess MeS^–, V (R = H) was obtained. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Application In Synthesis of 4-Bromo-1-methylimidazole).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Application In Synthesis of 4-Bromo-1-methylimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and cytotoxicity evaluation of novel C7-C7, C7-N3 and N3-N3 dimers of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (seco-CBI) with pyrrole and imidazole polyamide conjugates was written by Kumar, Rohtash;Lown, J. William. And the article was included in Organic & Biomolecular Chemistry in 2003.HPLC of Formula: 169770-25-6 This article mentions the following:

The C7-C7, C7-N3 and N3-N3 dimers of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (seco-CBI) with pyrrole and imidazole polyamides, e.g. I (n = 1 – 3; X = N, CH; R = Me₃CO₂C), were synthesized and their preliminary anticancer evaluation was carried out against three types of cancer cells. In the experiment, the researchers used many compounds, for example, Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 169770-25-6HPLC of Formula: 169770-25-6).

Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 169770-25-6) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.HPLC of Formula: 169770-25-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Novel NHC-coordinated ruthenium(II) arene complexes achieve synergistic efficacy as safe and effective anticancer therapeutics was written by Chen, Chao;Xu, Chang;Li, Tongyu;Lu, Siming;Luo, Fangzhou;Wang, Hangxiang. And the article was included in European Journal of Medicinal Chemistry in 2020.Application In Synthesis of 1-Octyl-1H-imidazole This article mentions the following:

There is an urgent need for more effective, less toxic cancer therapy agents. Motivated by this need, we synthesized a small panel of N-heterocyclic carbene (NHC)-coordinated ruthenium(II) arene complexes Ru1–Ru6 with the formula [Ru(p-cymene)(L)Cl]PF₆ (L = NHC ligand with varying substituents). Cell-based in vitro studies revealed that despite the structural similarity, Ru1–Ru6 exhibited distinct cytotoxic activities against cancer cells. In particular, Ru4 and Ru6, which bear n-octyl and pentamethylbenzyl motifs, resp., were the most active at inducing apoptosis. In human ovarian A2780 cancer cells, Ru4 and Ru6 showed the highest cytotoxicities with IC₅₀ values of 2.74 ± 0.15μM and 1.98 ± 0.10μM, resp., and they were approx. 2-fold more potent than cisplatin (IC₅₀ = 5.55 ± 0.37μM). In addition to the cell killing capacity, inhibition of cell migration was validated by using these two optimized complexes. Mechanistic studies revealed that Ru4 and Ru6 complexes induced apoptosis in a caspase-dependent manner, primarily through intracellular reactive oxygen species (ROS) overproduction and cell cycle arrest at G1 phase. Furthermore, in a preclin. metastatic model of A2780 tumor xenograft, administration of Ru4 and Ru6 (20μmol/kg) resulted in a marked inhibition of tumor progression and metastasis. Finally, a substantially alleviated systemic toxicity was observed for both complexes in comparison with cisplatin in animals. Overall, this study greatly increases our understanding of NHC-coordinated Ru(II) arene metallodrugs, aiding further investigation of their therapeutic potential in the treatment of metastatic cancers. 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. 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 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).Application In Synthesis of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effect of ionic liquids on the conformation of a porphyrin-based viscometer was written by Jameson, Laramie P.;Kimball, Joseph D.;Gryczynski, Zygmunt;Balaz, Milan;Dzyuba, Sergei V.. And the article was included in RSC Advances in 2013.Application In Synthesis of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

Structure of the cationic and anionic counterparts of ionic liquids has a significant impact on the conformational bias of the porphyrin rotor; an apparent correlation between the conformation and the viscosity of ionic liquids was noted, albeit it was found to be distinct and more complex from that found in mol. solvents. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Application In Synthesis of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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 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).Application In Synthesis of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Characterization of the chemical differences between solvent extracts from Pu-erh tea and Dian Hong black tea by CP-Py-GC/MS was written by Gong, Jia-shun;Tang, Chao;Peng, Chun-xiu. And the article was included in Journal of Analytical and Applied Pyrolysis in 2012.HPLC of Formula: 26832-08-6 This article mentions the following:

Solvent extracts from a type of Pu-erh tea and Dian Hong black tea were characterized by Curie-point pyrolysis-gas chromatog.-mass spectroscopy (CP-Py-GC/MS). The ethyl-acetate extracts from both teas showed similar CP-Py-GC/MS results, with main pyrolytic products of carbon dioxide, caffeine, o-phenols, and phthalate esters. During pyrolysis, the n-butanol extract from Pu-erh tea formed carbon dioxide (38.92% of total pyrolytic products), alkaloids (49.7%), and nitrogen oxides (8.38%), as well as a small fraction of esters. The n-butanol extract from Dian Hong tea formed mainly alcs., amines, esters, phenols, carboxylic acids, and alkaloids. The raw theabrownin extracts (ethanol precipitates) from the two teas produced substantially different CP-Py-GC/MS results. The raw theabrownin extract from Pu-erh tea formed mostly carbon dioxide during pyrolysis, whereas the counterpart extract from Dian Hong tea formed mainly carbon dioxide (48.23%) and nitrogen oxides (35.39%). The 3.5-100 kDa fractions separated from the theabrownin extracts of the two teas showed similar CP-Py-GC/MS results, whereas the fractions <3.5 kDa and >100 kDa formed substantially different pyrolytic products. These results showed that solvent extracts from Pu-erh tea and Dian Hong tea had substantially different chem. compositions and structures. The study suggested that CP-Py-GC/MS can be used to effectively identify chem. differences between tea extracts In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6HPLC of Formula: 26832-08-6).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Cu-Al composite as the negative electrode for long-life Al-ion batteries was written by Jiao, Handong;Jiao, Shuqiang;Song, Wei-Li;Chen, Haosen;Wang, Mingyong;Tu, Jiguo;Fang, Daining. And the article was included in Journal of the Electrochemical Society in 2019.COA of Formula: C4H7ClN2 This article mentions the following:

Rechargeable Al-ion batteries have attracted great interest due to their advantages in high anode capacity, high safety, etc. However, conventional Al foil neg. electrode has critical problems in corrosion and pulverization. Here, we propose a novel Cu-Al composite, which is prepared by a facile electrochem. plating approach, as the neg. electrode for addressing above challenges. Remarkably, the plated Cu foil neg. electrode delivers excellent stability and long cycle life compared with the Al foil neg. electrode, although its thickness and areal mass d. are only 30% and �6% of that of the Al foil neg. electrode, resp. The essential pulverization problem in bare Al neg. electrode would be dramatically reduced attributing to excellent corrosion resistance of Cu foil. Besides, the plated Al is still attached to the Cu foil during repeated charge-discharge processes, resulting in a nearly 100% Coulombic efficiency even after long-term cycling. More importantly, the plated Cu foil neg. electrode is convenient for the large-scale practical applications. In view of our results, this work opens an effective approach for configuring low-cost, high energy d., long cycle life and scalable neg. electrode of Al-ion batteries. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3COA of Formula: 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.COA of Formula: C4H7ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Discovery of imidazolidine-2,4-dione-linked HIV protease inhibitors with activity against lopinavir-resistant mutant HIV was written by Flosi, William J.;DeGoey, David A.;Grampovnik, David J.;Chen, Hui-ju;Klein, Larry L.;Dekhtyar, Tatyana;Masse, Sherie;Marsh, Kennan C.;Mo, Hong Mei;Kempf, Dale. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

A new series of HIV protease inhibitors has been designed and synthesized based on the combination of the (R)-(hydroxyethylamino)sulfonamide isostere and the cyclic urea component of lopinavir. The series was optimized by replacing the 6-membered cyclic urea linker with an imidazolidine-2,4-dione which readily underwent N-alkylation to incorporate various methylene-linked heterocycle groups that bind favorably in site 3 of HIV protease. Significant improvements compared to lopinavir were seen in cell culture activity vs. wild-type virus (pNL4-3) and the lopinavir-resistant mutant virus A17 (generated by in vitro serial passage of HIV-1 (pNL4-3) in MT-4 cells). Select imidazolidine-2,4-dione containing PIs were also more effective at inhibiting highly resistant patient isolates Pt1 and Pt2 than lopinavir. Pharmacokinetic data collected for compounds in this series varied considerably when coadministered orally in the rat with an equal amount of ritonavir (5 mg/kg each). The AUC values ranged from 0.144 to 12.33 μg h/mL. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Regulation of the Metal Center and Coordinating Anion of Mononuclear Ln(III) Complexes to Promote an Efficient Luminescence Response to Various Organic Solvents was written by Wang, Hui-Feng;Ma, Xiong-Feng;Zhu, Zhong-Hong;Zou, Hua-Hong;Liang, Fu-Pei. And the article was included in Langmuir in 2020.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

A series of mononuclear lanthanide complexes [Ln(L1)(NO₃)₃], (Ln = Dy(III), 1; Tb(III), 3; and Eu(III), 4; L1 = (N¹E,N²E)-N¹,N²-bis((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)cyclohexane-1,2-diamine) is obtained by reacting N-methylbenzimidazole-2-carbaldehyde (L2) and 1,2-cyclohexanediamine (L3) with Ln(NO₃)₃·6H₂O under solvothermal conditions. L1 ligand is produced via an in situ Schiff base reaction of two mols. of L2 and one mol. of L3. The metal center Ln(III) is in a N₄O₆ environment formed by L1 and NO₃^–. NaSCN is added on the basis of 1 synthesis. One SCN^– replaces one of the three coordinated NO₃^– anions in the 1 structure, and the complex [Dy(L1)(NO₃)₂(SCN)]·CH₃CN (2) is synthesized. The complex 1 shows excellent luminescence response to petroleum ether (PET), an organic solvent. To the best of our knowledge, this study is the first to use a complex for sensing responses to PET. When the metal center is changed, the obtained mononuclear complexes 3 and 4 show an excellent luminescence response to THF. Lastly, 2 obtained by changing the coordinating anion shows an excellent luminescence response to dichloromethane. Herein, for the first time, we regulate the metal center and coordinating anion of lanthanide complexes to adjust the recognition and response of these complexes to different organic solvents. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

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. 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.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Iridium-catalyzed Synthesis of Saturated N-Heterocycles from Aldehydes and SnAP Reagents with Continuous Flow Photochemistry was written by Jindakun, Chalupat;Hsieh, Sheng-Ying;Bode, Jeffrey W.. And the article was included in Organic Letters in 2018.Synthetic Route of C9H8N2O This article mentions the following:

Com. available tin amine protocol (SnAP) reagents provide a simple approach to the synthesis of a wide variety of saturated N-heterocycles from aldehydes. In this report, we disclose that the copper(II) promoter and hexafluoroisopropanol can be replaced by photocatalytic conditions using Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆ in CH₃CN. Continuous flow photochem. conditions provide a clean, scalable approach to valuable products including morpholines, piperazines, thiomorpholines, diazepanes, and oxazepanes from aldehyde starting materials. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Synthetic Route of C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Synthetic Route of C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Mechanisms of hydrogen bond formation between ionic liquids and cellulose and the influence of water content was written by Rabideau, Brooks D.;Ismail, Ahmed E.. And the article was included in Physical Chemistry Chemical Physics in 2015.Electric Literature of C7H13ClN2 This article mentions the following:

We study the dynamics of the formation of multiple hydrogen bonds between ionic liquid anions and cellulose using mol. dynamics simulations. We examine fifteen different ionic liquids composed of 1-alkyl-3-methylimidazolium cations ([C_nmim], n = 1, 2, 3, 4, 5) paired with either chloride, acetate or dimethylphosphate. We map the transitions of anions hydrogen bonded to cellulose into different bonding states. We find that increased tail length in the ionic liquids has only a very minor effect on these transitions, tending to slow the dynamics of the transitions and increasing the hydrogen bond lifetimes. Each anion can form up to four hydrogen bonds with cellulose. We find that this hydrogen bond “redundancy” leads to multiply bonded anions having lifetimes three to four times that of singly bound anions. Such redundant hydrogen bonds account for roughly half of all anion-cellulose hydrogen bonds. Addnl. simulations for [C₂mim]Cl, [C₂mim]Ac and [C₂mim]DMP were performed at different water concentrations between 70 mol% and 90 mol%. It was found that water crowds the hydrogen bond-accepting sites of the anions, preventing interactions with cellulose. The more water that is present in the system, the more crowded these sites become. Thus, if a hydrogen bond between an anion and cellulose breaks, the likelihood that it will be replaced by a nearby water mol. increases as well. We show that the formation of these “redundant” hydrogen bonding states is greatly affected by the presence of water, leading to steep drops in hydrogen bonding between the anions and cellulose. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Electric Literature of C7H13ClN2).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) 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 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.Electric Literature of C7H13ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem