Month: February 2023

The effect of an electron-withdrawing group in the imidazolium cation: the case of nitro-functionalized imidazolium salts as acidic catalysts for the acetylation of glycerol was written by Morais, Eduardo M.;Grillo, Igor B.;Stassen, Hubert K.;Seferin, Marcus;Scholten, Jackson D.. And the article was included in New Journal of Chemistry in 2018.Quality Control of 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

The acetylation of glycerol was achieved with high conversion and selectivity towards triacetin at low temperatures and short reaction times by using acidic imidazolium salts as catalysts. Moreover, the addition of a nitro group to the imidazolium cation affords a much more competent catalyst, indicating a significant effect provided by the simple electronic change in the imidazolium cation. Theor. calculations revealed increased polarization of the acidic hydrogen bond on the nitrated salts, which may be related to their superior catalytic behavior when compared to the non-functionalized salts. Combining the preliminary exptl. and theor. results, it is possible to suppose that the catalytic activity of acidic imidazolium salts may be better comprehended by its Bronsted acidities, but other parameters such as hardness, electronegativity, electrophilicity and ion-pair binding energy were also evaluated in order to investigate their effects in the acetylation of glycerol promoted by these acidic imidazolium salts. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Quality Control of 1-Methyl-1H-imidazol-3-ium chloride).

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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Quality Control of 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Unraveling the antitrypanosomal mechanism of benznidazole and related 2-nitroimidazoles: From prodrug activation to DNA damage was written by Dattani, Ambika;Drammeh, Isatou;Mahmood, Aishah;Rahman, Mahbubur;Szular, Joanna;Wilkinson, Shane R.. And the article was included in Molecular Microbiology in 2021.Application In Synthesis of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:

Nitroheterocycles represent an important class of compound used to treat trypanosomiasis. They often function as prodrugs and can undergo type I nitroreductase (NTR1)-mediated activation before promoting their antiparasitic activities although the nature of these downstream effects has yet to be determined Here, we show that in an NTR1-dependent process, benznidazole promotes DNA damage in the nuclear genome of Trypanosoma brucei, providing the first direct link between activation of this prodrug and a downstream trypanocidal mechanism. Phenotypic and protein expression studies revealed that components of the trypanosome′s homologous recombination (HR) repair pathway (TbMRE11, γH2A, TbRAD51) cooperate to resolve the benznidazole-induced damage, indicating that the prodrug-induced lesions are most likely double stand DNA breaks, while the sequence/recruitment kinetics of these factors parallels that in other eukaryotes HR systems. When extended to other NTR1-activated 2-nitroimidazoles, some were shown to promote DNA damage. Intriguingly, the lesions induced by these required TbMRE11 and TbCSB activities to fix leading us to postulate that TbCSB may operate in systems other than the transcription-coupled nucleotide excision repair pathway. Understanding how existing trypanosomal drugs work will aid future drug design and help unlock novel reactions/pathways that could be exploited as targets for therapeutic intervention. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Application In Synthesis 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. 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Application In Synthesis of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and pharmacological activity of aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals was written by Anisimova, V. A.;Tolpygin, I. E.;Spasov, A. A.;Kosolapov, V. A.;Stepanov, A. V.;Orlova, A. A.;Naumenko, L. V.. And the article was included in Pharmaceutical Chemistry Journal in 2007.Application of 24134-26-7 This article mentions the following:

The synthesis and pharmacol. properties of a series of hydroxybenzoylmethylimidazo- and pyrimidobenzimidazoles are described. Most of the products exhibit a high antioxidant activity, possess pronounced hemorheol. properties, and influence the blood glucose level. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Application of 24134-26-7).

2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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 of 24134-26-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Toughening Poly(lactic acid) with Imidazolium-based Elastomeric Ionomers was written by Chen, Lu;Hu, Kuan;Sun, Si-Ting;Jiang, Hai;Huang, Dong;Zhang, Kun-Yu;Pan, Li;Li, Yue-Sheng. And the article was included in Chinese Journal of Polymer Science in 2018.Related Products of 21252-69-7 This article mentions the following:

Imidazolium-based elastomeric ionomers (i-BIIR) were facilely synthesized by ionically modified brominated poly(isobutylene-co-isoprene) (BIIR) with different alkyl chain imidazole and thoroughly explored as novel toughening agents for poly(lactic acid) (PLA). The miscibility, thermal behavior, phase morphol. and mech. property of ionomers and blends were investigated through dynamic mech. analyses (DMA), differential scanning calorimetry (DSC), SEM, tensile and impact testing. DMA and SEM results showed that better compatibility between the PLA and i-BIIR was achieved compared to the PLA/unmodified BIIR elastomer. A remarkable improvement in ductility with an optimum elongation at break up to 235% was achieved for the PLA/i-BIIR blends with 1-dodecylimidazole alkyl chain (i-BIIR-12), more than 10 times higher than that of pure PLA. The impact strengths of PLA were enhanced from 1.9 kJ/m² to 4.1 kJ/m² for the PLA/10 wt% i-BIIR-12 blend. Toughening mechanism had been established by systematical anal. of the compatibility, intermol. interaction and phase structures of the blends. Interfacial cavitations initiated massive shear yielding of the PLA matrix owing to a suitable interfacial adhesion which played a key role in the enormous toughening effect in these blends. We believed that introducing imidazolium group into the BIIR elastomer was vital for the formation of a suitable interfacial adhesion. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Related Products of 21252-69-7).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Integration of multi-scale molecular modeling approaches with experiments for the in silico guided design and discovery of novel hERG-Neutral antihypertensive oxazalone and imidazolone derivatives and analysis of their potential restrictive effects on cell proliferation was written by Durdagi, Serdar;Aksoydan, Busecan;Erol, Ismail;Kantarcioglu, Isik;Ergun, Yavuz;Bulut, Gulay;Acar, Melih;Avsar, Timucin;Liapakis, George;Karageorgos, Vlasios;Salmas, Ramin E.;Sergi, Baris;Alkhatib, Sara;Turan, Gizem;Yigit, Berfu Nur;Cantasir, Kutay;Kurt, Bahar;Kilic, Turker. And the article was included in European Journal of Medicinal Chemistry in 2018.Name: 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 This article mentions the following:

AT1 antagonists is the most recent drug class of mols. against hypertension and they mediate their actions through blocking detrimental effects of angiotensin II (A-II) when acts on type I (AT1) A-II receptor. The effects of AT1 antagonists are not limited to cardiovascular diseases. AT1 receptor blockers may be used as potential anti-cancer agents – due to the inhibition of cell proliferation stimulated by A-II. Therefore, AT1 receptors and the A-II biosynthesis mechanisms are targets for the development of new synthetic drugs and therapeutic treatment of various cardiovascular and other diseases. Multi-scale mol. modeling approaches were performed and it is found that oxazolone and imidazolone derivatives reveal similar/better interaction energy profiles compared to the FDA approved sartan mols. at the binding site of the AT1 receptor. In silico-guided designed hit mols. were then synthesized and tested for their binding affinities to human AT1 receptor in radioligand binding studies, using [¹²⁵I-Sar¹-Ile⁸] AngII. Among the compounds tested, 19d (4′-((4-(4-bromobenzylidene)-2-butyl-5-oxo-4,5-dihydro-1H-imidazol-1-yl)methyl)[1,1′-biphenyl]-2-carbonitrile) and 9j (4-(2-bromobenzylidene)-2-butyl-1-((2′-(2-trityl-2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl)methyl)-1H-imidazol-5(4H)-one) mols. bound to receptor in a dose response manner and with relatively high affinities. Next, cytotoxicity and wound healing assays were performed for these hit mols. Since hit mol. 19d led to deceleration of cell motility in all three cell lines (NIH3T3, A549, and H358) tested in this study, this mol. is investigated in further tests. In two cell lines (HUVEC and MCF-7) tested, 19d induced G2/M cell cycle arrest in a concentration dependent manner. Adherent cells detached from the plates and underwent cell death possibly due to apoptosis at 19d concentrations that induced cell cycle arrest. 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: 145040-37-5Name: 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).

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. 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.Name: 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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On the relation between reorientation and diffusion in glass-forming ionic liquids with micro-heterogeneous structures was written by Becher, Manuel;Steinruecken, Elisa;Vogel, Michael. And the article was included in Journal of Chemical Physics in 2019.Recommanded Product: 404001-48-5 This article mentions the following:

We investigate complex structure-dynamics relations in glass-forming ionic liquids comprising 1-alkyl-3-methylimidazolium cations and bis(trifluoromethylsulfonyl)imide anions. In doing so, we exploit the microheterogeneous structures emerging when the alkyl length is increased in the range n = 1-12 and use that ^1H and ²H NMR give information about cation dynamics, while ¹⁹F NMR reports on anion motions. Furthermore, we combine spin-lattice relaxation anal., including field-cycling relaxometry, with stimulated-echo experiments to follow reorientation dynamics related to structural relaxation in wide dynamic ranges and we apply static field gradients to probe translational diffusion. The resulting correlation times τ and diffusion coefficients D show Vogel-Fulcher-Tammann temperature dependence. Moreover, they indicate a moderate slowdown of both cation and anion dynamics with increasing alkyl length n. However, the relative diffusivities of the ionic species depend on the cation size, where cations are more mobile for n < 6 and anions for n > 6. Finally, we relate rotational and translational motions in the framework of the Stokes-Einstein-Debye (SED) approach. We find that the SED relation is obeyed for anion dynamics in all samples, while it breaks down for cation dynamics when n is increased. The origin of this SED breakdown is shown to differ fundamentally from that reported previously for conventional glass formers. We argue that an emergence of cation clusters causes a retardation of cation diffusion relative to cation reorientation upon cooling, i.e., the studied ionic liquids show a complex interplay of structural and dynamical properties. (c) 2019 American Institute of Physics. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Recommanded Product: 404001-48-5).

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. 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: 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Dichlorophenylacrylonitriles as AhR Ligands That Display Selective Breast Cancer Cytotoxicity in vitro was written by Baker, Jennifer R.;Gilbert, Jayne;Paula, Stefan;Zhu, Xiao;Sakoff, Jennette A.;McCluskey, Adam. And the article was included in ChemMedChem in 2018.Category: imidazoles-derivatives This article mentions the following:

Knoevenagel condensation of 3,4-dichloro- and 2,6-dichlorophenylacetonitriles gave a library of dichlorophenylacrylonitriles. Our leads (Z)-2-(3,4-dichlorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile (5) and (Z)-2-(3,4-dichlorophenyl)-3-(4-nitrophenyl)acrylonitrile (6) displayed 0.56±0.03 and 0.127±0.04 μM growth inhibition (GI₅₀) and 260-fold selectivity for the MCF-7 breast cancer cell line. A 2,6-dichlorophenyl moiety saw a 10-fold decrease in potency; addnl. nitrogen moieties (-NO₂) enhanced activity (Z)-2-(2,6-dichloro-3-nitrophenyl)-3-(2-nitrophenyl)acrylonitrile (26) and (Z)-2-(2,6-dichloro-3-nitrophenyl)-3-(3-nitrophenyl)acrylonitrile (27), with the corresponding -NH₂ analogs (Z)-2-(3-amino-2,6-dichlorophenyl)-3-(2-aminophenyl)acrylonitrile (29) and (Z)-2-(3-amino-2,6-dichlorophenyl)-3-(3-aminophenyl)acrylonitrile (30) being more potent. Despite this, both 29 (2.8±0.03 μM) and 30 (2.8±0.03 μM) were found to be 10-fold less cytotoxic than 6. A bromine moiety effected a 3-fold enhancement in solubility with (Z)-3-(5-bromo-1H-pyrrol-2-yl)-2-(3,4-dichlorophenyl)acrylonitrile 18 relative to 5 at 211 μg mL^-1. Modeling-guided synthesis saw the introduction of 4-aminophenyl substituents (Z)-3-(4-aminophenyl)-2-(3,4-dichlorophenyl)acrylonitrile (35) and (Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide (38), with resp. GI₅₀ values of 0.030±0.014 and 0.034±0.01 μM. Other analogs such as 35 and 36 were found to have sub-micromolar potency against our panel of cancer cell lines (HT29, colon; U87 and SJ-G2, glioblastoma; A2780, ovarian; H460, lung; A431, skin; Du145, prostate; BE2-C, neuroblastoma; MIA, pancreas; and SMA, murine glioblastoma), except compound 38 against the U87 cell line. A more extensive evaluation of 38 ((Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide) in a panel of drug-resistant breast carcinoma cell lines showed 10-206 nM potency against MDAMB468, T47D, ZR-75-1, SKBR3, and BT474. Mol. Operating Environment docking scores showed a good correlation between predicted binding efficiencies and observed MCF-7 cytotoxicity. This supports the use of this model in the development of breast-cancer-specific drugs. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4Category: imidazoles-derivatives).

1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4) 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.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

NMR Quantification of Halogen-Bonding Ability To Evaluate Catalyst Activity was written by Chang, Yun-Pu;Tang, Teresa;Jagannathan, Jake R.;Hirbawi, Nadia;Sun, Shaoming;Brown, Jonah;Franz, Annaliese K.. And the article was included in Organic Letters in 2020.Safety of 1-Methylbenzimidazole This article mentions the following:

Quantification of halogen-bonding abilities is described for a series of benzimidazolium-, imidazolium- and bis(imidazolium) halogen-bond donors (XBDs) using ³¹P NMR spectroscopy. The measured Δδ(³¹P) values correlate with calculated activation free energy ΔG^{â€?/sup> and catalytic activity for a Friedel-Crafts indole addition This rapid method also serves as a sensitive indicator for Bronsted acid impurities. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Safety of 1-Methylbenzimidazole).}

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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Safety of 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Polarographic investigations in the imidazole and thiazole series. Nitro derivatives, aldehydes, and halogen derivatives was written by Laviron, E.. And the article was included in Abhandl. Deut. Akad. Wiss. Berlin, Kl. Chem., Geol. Biol. in 1964.Application of 3034-41-1 This article mentions the following:

4-(5)-Nitroimidazole,-2-nitroimidazole, 4-nitro- and 5-nitro-l-methylimidazole, and 4-(5)nitro-1,3-dimethylimidazolium iodide (I) are reduced in 2 steps, but the 2nd step is not equally sharp in all cases. Ε_1/2 is a linear function of pH for 2- nitroimidazole and I but not for the other compounds The diffusion current of 2-nitroimidazole is diminished at low pH. This is also true of the 5-nitro derivatives of thiazole (with NH₂, NHAc, Cl, Br, or OH substituted in position 2). 4(5)-Imidazolecarboxaldehyde and thiazolecarboxaldehyde in buffered aqueous and in absolute EtOH and MeOH solutions, acidified with H₂SO₄ or buffered with acetate and HOAc, show a marked lowering of the diffusion current in acid medium. This was ascribed to a polarographically irreducible hydrate of the imidazolium or thiazolium ion in acid, a hypothesis that was further supported by uv spectra. Of numerous halogen derivatives investigated, all compounds in the thiazol series are very easily reducible, while only the 2-iodo and 2,4,5-triiodo compounds give well defined waves in the imidazole series. At the extremes of pH, the Ε_1/2 of the halogen derivatives are independent of pH, while a more or less linear dependence on pH (with varying slope) is found for intermediate values of pH. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application of 3034-41-1).

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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Application of 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Metalation and metal-halogen exchange reactions of imidazoles was written by Iddon, Brian;Lim, Bee Lan. And the article was included in Journal of the Chemical Society, Chemical Communications in 1981.Application In Synthesis of 4-Bromo-1-methylimidazole This article mentions the following:

Imidazoles I (R = SPh, R¹ = H, R² = H, MeS) underwent lithiation and sulfuration to give thioimidazoles. E.g., I (R = SPh, R¹ = R² = H) was treated with BuLi in THF at -78° followed by addition of (PhS)₂ to give I (R = R² = SPh, R¹ = H) quant. Similar treatment of I (R-R² = Br) gave 67% I (R = SPh, R¹ = R² = Br). 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 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 4-Bromo-1-methylimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem