Category: imidazoles-derivatives

Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines was written by Quinonero, Ophelie;Jean, Marion;Vanthuyne, Nicolas;Roussel, Christian;Bonne, Damien;Constantieux, Thierry;Bressy, Cyril;Bugaut, Xavier;Rodriguez, Jean. And the article was included in Angewandte Chemie, International Edition in 2016.Related Products of 85692-37-1 This article mentions the following:

Suitably substituted enantioenriched 4-aryl-1,4-dihydro-pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO₂ into axially chiral 4-arylpyridines with central-to-axial chirality conversion. Moderate to complete percentages (cp) were observed, and a model for the conversion of chirality is discussed. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Related Products of 85692-37-1).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) 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).Related Products of 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Interaction of Imidazolium-Based Room-Temperature Ionic Liquids with DOPC Phospholipid Monolayers: Electrochemical Study was written by Galluzzi, Massimiliano;Zhang, Shengwen;Mohamadi, Shahrzad;Vakurov, Alexander;Podesta, Alessandro;Nelson, Andrew. And the article was included in Langmuir in 2013.Related Products of 404001-48-5 This article mentions the following:

To test the biocompatible character of room-temperature ionic liquids (ILs), the interaction of various ILs with biol. membrane (biomembrane) models was studied. Dioleoyl phosphatidylcholine (DOPC) adsorbed on a Hg electrode forms an impermeable defect-free monolayer which is a well established biomembrane model, prone to be studied by electrochem. techniques. The authors have monitored the modifications of the Hg supported monolayer caused by ILs using rapid cyclic voltammetry (RCV), a.c. voltammetry (ACV), and electrochem. impedance spectroscopy (EIS). Imidazolium-based ILs were studied whose interaction highlighted the role of anion and lateral side chain of cation during the interaction with DOPC monolayers. The hydrophobic and lipophilic character of the IL cations is a primary factor responsible for this interaction. Hg-supported monolayers provide an accurate anal. of the behavior of ILs at the interface of a biomembrane leading to a comprehensive understanding of the interaction mechanisms involved. At the same time, these experiments show that the Hg-phospholipid model is an effective toxicity sensing technique as shown by the correlation between literature in vivo toxicity data and the data. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Related Products of 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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Related Products of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

FTIR metabolomic fingerprint reveals different modes of action exerted by active pharmaceutical ingredient based ionic liquids (API-ILs) on Salmonella typhimurium was written by Mester, P.;Jehle, A. K.;Leeb, C.;Kalb, R.;Grunert, T.;Rossmanith, P.. And the article was included in RSC Advances in 2016.Name: 1-ethyl-2,3-dimethylimidazolium chloride This article mentions the following:

Since their incorporation into various chem. and biochem. processes, ionic liquids (ILs) have now been found useful for biomedical applications, including active pharmaceutical ingredients (APIs) such as antimicrobial agents or antibiotics. Recently, synergistic API-ILs with great potential have been reported, which show either increased antimicrobial activity or the ability to overcome bacterial resistance. In this study a total of 19 API-ILs, based on the antibiotic nalidixic acid, combined with different cation species, were investigated for synergistic effects against the important foodborne pathogen Salmonella. Furthermore, 19 resp. ILs with chloride as the anion were used to control the effects of the different cation species. The antimicrobial activities of all 38 ILs against six different Salmonella species, as well as two nalidixic acid-resistant S. typhimurium strains, were determined via the microbroth dilution assay. The response pattern of the main cellular constituents, namely proteins, carbohydrates, and lipids of the bacterial cells to the most promising API-ILs was further investigated by Fourier transform IR (FTIR) spectroscopy. While a number of active API-ILs based on nalidixic acid could be synthesized, no evidence for synergistic effects, such as increased antimicrobial activity or the ability to overcome resistance was found with either microbiol. or spectroscopic methods. However, it could be demonstrated for the first time that while the different IL species ([TC₈MA]⁺ and [TMC₁₆A]⁺) showed similar antimicrobial activity, the FTIR spectral patterns indicated changes in bacterial membrane fluidity suggesting different modes of action. In the experiment, the researchers used many compounds, for example, 1-ethyl-2,3-dimethylimidazolium chloride (cas: 92507-97-6Name: 1-ethyl-2,3-dimethylimidazolium chloride).

1-ethyl-2,3-dimethylimidazolium chloride (cas: 92507-97-6) 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-ethyl-2,3-dimethylimidazolium chloride

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

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

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

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

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

Reductive cyclization of o-phenylenediamine with CO₂ and BH₃NH₃ to synthesize 1H-benzoimidazole derivatives was written by Li, Xiao;Zhang, Junhua;Yang, Yue;Hong, Hailong;Han, Limin;Zhu, Ning. And the article was included in Journal of Organometallic Chemistry in 2021.COA of Formula: C8H8N2 This article mentions the following:

A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO₂ and BH₃NH₃ to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH₃NH₃ promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramol. nucleophilic addition-elimination for the formation of target product. In this process, BH₃NH₃ served multifunctional roles, acting as a reducing agent and a formylation catalyst. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6COA of Formula: C8H8N2).

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) 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 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.COA of Formula: C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Counterion-specific shale hydration inhibiting performance of vinylimdazolium ionic liquids was written by Yang, Lili;Kong, Dechang;Chang, Xiangyang;Jiang, Guancheng;Ao, Tian;Xie, Chunlin;Kinkeyi Moukoko, Aurchy Dauriant;Ma, Jiaying. And the article was included in Journal of Molecular Liquids in 2021.Recommanded Product: 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) This article mentions the following:

The role of cation and the influence of the cation alkyl chain length of vinylimdazolium-based ionic liquid (IL) were studied previously to develop high-performance shale inhibitor for application in water-based drilling fluids (WBDFs). Results demonstrate that they have a considerable effect on the inhibition performance. However, the physicochem. properties can be tuned by changing the cation/anion combination. Therefore, the influence of anion type on the inhibiting performance must be investigated. In this study, we selected several vinylimdazolium-based ILs with different anions, such as bromide (Br-), tetrafluoroborate (BF-4), hexafluorophosphate (PF-6), and bis(trifluoromethylsulfonyl) (TFSI-). The size, solubility, hydrophilicity, and interaction in-between were tuned accordingly by changing the anion species. Results from linear swelling height, hot rolling recovery, and rheol. measurements show that the IL with bromide anion has the most outstanding shale inhibiting performance. The anions influence the inhibitory performance of ILs in a distinct manner from cations by measuring the properties of Na-Bent dispersions added with different anion-based ILs. The former produces different abilities to suppress elec. double layers and decreases the interlayer distance, whereas the latter mainly affects the interlayer distance. Despite different hydrophilic/hydrophobic properties, they have similar performance to inhibit the crystalline hydration and swelling. This condition is probably because they have a common cation that dominates the process of entering the interlayer void and narrowing interlayer spacing. Many hydrophilic ILs with anion Br- or BF-4 have the capacity to strongly resist the repel interaction between clay particles and prompt aggregation, leading to better inhibitory performance. Combined with the previous result, cations and anions affect the IL inhibiting ability although their underlying mechanism is different. Thus, this work explored the relationship between inhibiting performance and IL moiety. The findings provide consolidate theor. foundation for developing shale inhibitors for WBDFs. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9Recommanded Product: 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V)).

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. 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: 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V)

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem