Imidazoles-derivatives

Design, synthesis and biological evaluation of naphthalene-derived (arylalkyl)azoles containing heterocyclic linkers as new anticonvulsants: A comprehensive in silico, in vitro, and in vivo study was written by Valipour, Mehdi;Naderi, Nima;Heidarli, Elmira;Shaki, Fatemeh;Motafeghi, Farzaneh;Talebpour Amiri, Fereshteh;Emami, Saeed;Irannejad, Hamid. And the article was included in European Journal of Pharmaceutical Sciences in 2021.Name: 1-Methylbenzimidazole This article mentions the following:

In continuation of our research to find strong and safe anticonvulsant agents, a number of (arylalkyl)azoles (AAAs) containing naphthylthiazole and naphthyloxazole scaffolds were designed and synthesized. The in vivo anticonvulsant evaluations in BALB/c mice revealed that some of them had significant anticonvulsant activity in both maximal electroshock (MES) and pentylenetetrazole (PTZ) models of epilepsy. The best profile of activity was observed with compounds containing imidazole and triazole rings (C1, C6, G1, and G6). In particular, imidazolylmethyl-thiazole C1 with median ED (ED₅₀)= 7.9 mg/kg in the MES test, ED₅₀= 27.9 mg/kg in PTZ test, and without any sign of neurotoxicity (in the rotarod test, 100 mg/kg) was the most promising compound The patch-clamp recording was performed to study the mechanism of action of the representative compound C1 on hippocampal dentate gyrus (DG) cells. The results did not confirm any modulatory effect of C1 on the voltage-gated ion channels (VGICs) or GABA_A agonism, but suggested a significant reduction of excitatory postsynaptic currents (EPSCs) frequency on hippocampal DG neurons. Sub-acute toxicity studies revealed that administration of the most active compounds (C1, C6, G1, and G6) at 100 mg/kg bw/day for two weeks did not result in any mortality or significant toxicity as evaluated by assessment of biochem. markers such as lipid peroxidation, intracellular glutathione, total antioxidant capacity, histopathol. changes, and mitochondrial functions. Other pharmacol. aspects of compounds including mechanistic and ADME properties were investigated computationally and/or exptl. Mol. docking on the NMDA and AMPA targets suggested that the introduction of the heterocyclic ring in the middle of AAAs significantly affects the affinity of the compounds The obtained results totally demonstrated that the prototype compound C1 can be considered as a new lead for the development of anticonvulsant agents. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Name: 1-Methylbenzimidazole).

1-Methylbenzimidazole (cas: 1632-83-3) 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.Name: 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Photoinduced Heterogeneous C-H Arylation by a Reusable Hybrid Copper Catalyst was written by Choi, Isaac;Mueller, Valentin;Lole, Gaurav;Koehler, Robert;Karius, Volker;Vioel, Wolfgang;Jooss, Christian;Ackermann, Lutz. And the article was included in Chemistry – A European Journal in 2020.Application of 1632-83-3 This article mentions the following:

Heterogeneous copper catalysis enabled photoinduced C-H arylations of heteroarenes with aryl halides under exceedingly mild conditions at room temperature to afford aryl heteroarenes such as I [R = H, 6-OMe, 5-Cl, etc.; Ar = Ph, 4-MeC₆H₄, 2-MeOC₆H₄, etc.; X = O, S, NMe]. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS anal. of the hybrid copper catalyst, among others, supported its outstanding stability and reusability. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Application of 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) 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.Application of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of 2,3-dichloropropionitrile from chlorination of acrylonitrile catalyzed by ionic liquids was written by Li, Xuehui;Zheng, Binguo;Zhao, Jinggan. And the article was included in Cuihua Xuebao in 2006.Safety of 1-Methyl-3-propylimidazolium Chloride This article mentions the following:

Ionic liquids formed by imidazolium and pyridinium cations with Cl^–, Br^–, BF^–₄, and PF^–₆ anions were used for the catalytic synthesis of 2,3-dichloropropionitrile by the chlorination of acrylonitrile. The ionic liquids containing Cl^– and Br^– show good catalytic properties. The Cl^– and Br^– ions act as strong Lewis bases and mol. chlorine is activated by the induction effect of Cl^– and Br^–. Due to the stronger steric hindrance effect of the BF^–₄ and PF^–₆ anions, the chlorination of acrylonitrile is limited in the ionic liquids containing BF^–₄ and PF^–₆ anions. 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

Gemini imidazolium salts comprising Cl^–, BF^–₄, PF^–₆, AuCl^–₄ counterions: synthesis, thermotropic liquid crystal study and use of AuCl^–₄ salt precursor to AuNPs was written by Huang, Roy T. W.;Rondla, Rohini;Wang, Wen-Jwu;Lin, Ivan J. B.. And the article was included in Journal of Molecular Liquids in 2017.Application In Synthesis of 1-Octyl-1H-imidazole This article mentions the following:

The synthesis and thermotropic liquid crystal (LC) properties of gemini imidazolium salts comprising Cl^–, BF^–₄, PF^–₆, AuCl^–₄ counter anions, varied alkenyl spacer lengths and terminal alkyl chains are described. LC properties are investigated by differential scanning calorimetry, polarizing optical microscopy, and powder X-ray diffraction studies. It should be noted that, salts of short spacers favor the formation of mesophase. A SmA with wide mesophase range and high thermal stability are identified. The Cl^– salts have shown an odd-even effect on phase transition temperatures as the length and parity of the spacer is varied. The use of [(CH₂)₄(C₁₈-Im)₂][AuCl₄]₂ salt as precursor for the fabrication of Au nano/micro particles via chem. reduction, photo irradiation, and thermolysis methods is presented. A clear vision of morphol. change is observed in Au structures by varying the reduction method, however the mesophase does not control over the size and morphol. of Au particles in the thermolysis method. The colloidal AuNPs prepared in this study showed remarkable stability for over six months. These results offer great insight into the counter anion and spacer effects on LC nature of gemini Im salts, which broadens the scientific understanding to develop advanced soft materials. 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Application In Synthesis of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Azobenzene-Based Organic Salts with Ionic Liquid and Liquid Crystalline Properties was written by Stappert, Kathrin;Muthmann, Johanna;Spielberg, Eike T.;Mudring, Anja-Verena. And the article was included in Crystal Growth & Design in 2015.Related Products of 21252-69-7 This article mentions the following:

Two sets of new azobenzene-based bromide salts are synthesized, and their thermal photochromic properties are studied. Both sets are based on the imidazolium cation. The first set (1) features a sym. biscation where two imidazolium head groups (Im) with different alkyl chains (Cn) are connected to a central azobenzene unit (Azo): [Azo(C1-Im-Cn)₂]; n = 6, 8, 10, 12, 14. The other one contains an n-alkyl-imidazolium cation (Cn-Im) bearing a terminal azobenzene unit (C1-Azo) substituted with an alkoxy chain (O-Cm) of either two (2) or six (3) carbon atoms: [C1-Azo-O-Cm-Im-Cn]; m = 2, n = 8, 10, 12 and m = 6, n = 8, 10, 12, 14, 16. For both cation classes, the influence of alkyl chains of varying length on the thermal phase behavior was investigated by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). For five compounds (Azo(-C1-Im-C12)₂ (1d), Azo(-C1-Im-C12)₂ (1e), C1-Azo-O-C2-Im-C10 (2b), C1-Azo-O-C2-Im-C12 (2c), and C1-Azo-O-C6-Im-C16 (3e)), the formation of a liquid crystalline phase was observed The biscationic salts (1) are all comparatively high melting organic salts (180-240 °C), and only the two representatives with long alkylchains (C12 and C14) exhibit liquid crystallinity. The monocationic salts with an O-C2 bridge (2) melt between 140 and 170 °C depending on the alkyl chain length, but from an alkyl chain of 10 and more carbon atoms on they form a smectic A liquid crystalline phase. The representatives of the third set with a O-C6 bridge qualify as ionic liquids with m.ps. less than 100 °C. However, only the representative with a hexadecyl chain forms a liquid crystalline phase. Representative single crystals for all sets of cations could be grown that allowed for single crystal structure anal. Together with small-angle X-ray scattering experiments they allow for a more detailed understanding of the thermal properties. Through irradiation with UV-light (320-366 nm) all compounds undergo trans-cis isomerization, which reverses under visible light (440 nm). 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 a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Related Products of 21252-69-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Interionic Interactions in Imidazolic Ionic Liquids Probed by Soft X-ray Absorption Spectroscopy was written by Rodrigues, Fabio;Galante, Douglas;do Nascimento, Gustavo M.;Santos, Paulo S.. And the article was included in Journal of Physical Chemistry B in 2012.Quality Control of 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

This work studies pure ionic liquids (ILs) derived from an imidazolium ring with different carbonic chains and halides or bis(trifluoromethanesulfonilimide) (TFSI^–) as anions, using x-ray absorption near edge spectroscopy (XANES) at different energies (N, S, O, F, and Cl edges) to probe the interionic interactions. XANES data show that the interaction with the anion is weaker when the cation is an imidazolium than when the salt is formed by smaller cations, as Li, independently of the length of the carbonic chain attached to the imidazolium cation. Also for all studied ILs, it is not observed any influence of the anion on the XANES spectra of the cation, nor the opposite. 1-Methylimidazolium with Cl^–, a small and strongly coordinating anion, presents in the N K XANES spectrum a splitting of the band corresponding to N in the imidazolic ring, indicating two different chem. environments. For this cation with TFSI^–, on the contrary, this splitting was not observed, showing that the anion has a weaker interaction with the imidazolic ring, even without a lateral carbonic chain. 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. 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.Quality Control of 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

KOtBu-Catalyzed 1,2-Silaboration of N-Heteroarenes to Access 2-Silylheterocycles: A Cooperative Model for the Regioselectivity was written by Jeong, Eunchan;Heo, Joon;Jin, Seongho;Kim, Dongwook;Chang, Sukbok. And the article was included in ACS Catalysis in 2022.HPLC of Formula: 1632-83-3 This article mentions the following:

Reductive functionalization of N-heteroarenes offers a route to highly versatile heterocyclic synthons bearing multiple transformable groups. The authors present herein the development of KOtBu-catalyzed 1,2-silaboration of a broad range of N-heteroarenes, affording heterocyclic allylamines or enamines with the formation of a sp³ C2-Si bond. These labile compounds were isolated either as their N-acyl derivatives or as rearomatized 2-silyl-N-heteroarenes by the 1-pot procedures. A model of the six-membered ion-pair complex is proposed to rationalize the observed 1,2-regioselectivity, wherein KOtBu catalyst plays an associative role in activating the substrate and silylborane reagent. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3HPLC of Formula: 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) 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.HPLC of Formula: 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Hydrothermal syntheses, structures, and properties of the first examples of lanthanide 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoate complexes was written by Wen, Hui-Liang;Wen, Wen;Li, Dan-Dan;Liu, Chong-Bo;He, Min. And the article was included in Journal of Coordination Chemistry in 2013.Formula: C22H16N2O2 This article mentions the following:

Three new lanthanide coordination polymers with 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoic acid (H₂PA), [Ln(HPA)₃(H₂O)₂]·2H₂O [Ln = Pr (1); Eu (2); Er (3)] were obtained by hydrothermal syntheses and characterized by single crystal x-ray diffraction, elemental anal., IR spectroscopy, and powder X-ray diffraction. Complexes 1–3 are isomorphous 2-dimensional supramol. structures, in which lanthanide ions are bridged by carboxyl groups of HPA^– to form 1-dimensional chain structures, and the chains are further linked to 2-dimensional supramol. structures by hydrogen bonds. HPA^– exhibit chelating and μ₂-bridging coordination mode. The TGA of was carried out to examine the thermal stability and the photoluminescence of was investigated. In the experiment, the researchers used many compounds, for example, 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5Formula: C22H16N2O2).

4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5) 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 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).Formula: C22H16N2O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nonchromatographic Speciation of Selenium in Edible Oils Using Dispersive Liquid-Liquid Microextraction and Electrothermal Atomic Absorption Spectrometry was written by Lopez-Garcia, Ignacio;Vicente-Martinez, Yesica;Hernandez-Cordoba, Manuel. And the article was included in Journal of Agricultural and Food Chemistry in 2013.Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

A methodol. for the nonchromatog. separation of the main selenium species present in edible oils is presented. Dispersive liquid-liquid microextraction is used to extract inorganic selenium (iSe), seleno-L-cystine (SeCys₂), seleno-L-methionine (SeMet), and selenocystamine (SeCM) into a slightly acidic aqueous medium. The selenium total (tSe) content is measured in the extracts by electrothermal at. absorption spectrometry. By repeating the microextraction stage using an ionic liquid instead of water, the sum of SeCys₂, SeMet, and SeCM is obtained and iSe is calculated by difference. The detection limit is 0.03 ng of Se per g of oil. The fractionation of the edible oils by solid phase extraction followed by dispersive liquid-liquid extraction and at. absorption measurement also permits speciation of iSe to be carried out. Data for tSe and iSe levels of 15 samples of different origin are given. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Name: 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. 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 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.Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Prevention of Cardiac Dysfunction During Adjuvant Breast Cancer Therapy (PRADA): Extended Follow-Up of a 2×2 Factorial, Randomized, Placebo-Controlled, Double-Blind Clinical Trial of Candesartan and Metoprolol was written by Heck, Siri Lagethon;Mecinaj, Albulena;Ree, Anne Hansen;Hoffmann, Pavel;Schulz-Menger, Jeanette;Fagerland, Morten Wang;Gravdehaug, Berit;Rosjo, Helge;Steine, Kjetil;Geisler, Juergen;Gulati, Geeta;Omland, Torbjorn. And the article was included in Circulation in 2021.Product Details of 145040-37-5 This article mentions the following:

Adjuvant breast cancer therapy containing anthracyclines with or without anti-human epidermal growth factor receptor-2 antibodies and radiotherapy is associated with cancer treatment-related cardiac dysfunction. In the PRADA trial (Prevention of Cardiac Dysfunction During Adjuvant Breast Cancer Therapy), concomitant treatment with the angiotensin receptor blocker candesartan attenuated the reduction in left ventricular ejection fraction (LVEF) in women receiving treatment for breast cancer, whereas the β-blocker metoprolol attenuated the increase in cardiac troponins. This study aimed to assess the long-term effects of candesartan and metoprolol or their combination to prevent a reduction in cardiac function and myocardial injury. In this 2×2 factorial, randomized, placebo-controlled, double-blind, single-center trial, patients with early breast cancer were assigned to concomitant treatment with candesartan cilexetil, metoprolol succinate, or matching placebos. Target doses were 32 and 100 mg, resp. Study drugs were discontinued after adjuvant therapy. All 120 validly randomized patients were included in the intention-to-treat anal. The primary outcome measure was change in LVEF assessed by cardiovascular magnetic resonance imaging from baseline to extended follow-up. Secondary outcome measures included changes in left ventricular volumes, echocardiog. peak global longitudinal strain, and circulating cardiac troponin concentrations A small decline in LVEF but no significant between-group differences were observed from baseline to extended follow-up, at a median of 23 mo (interquartile range, 21 to 28 mo) after randomization (candesartan, 1.7% [95% CI, 0.5 to 2.8]; no candesartan, 1.8% [95% CI, 0.6 to 3.0]; metoprolol, 1.6% [95% CI, 0.4 to 2.7]; no metoprolol, 1.9% [95% CI, 0.7 to 3.0]). Candesartan treatment during adjuvant therapy was associated with a significant reduction in left ventricular end-diastolic volume compared with the noncandesartan group (P=0.021) and attenuated decline in global longitudinal strain (P=0.046) at 2 years. No between-group differences in change in cardiac troponin I and T concentrations were observed Anthracycline-containing adjuvant therapy for early breast cancer was associated with a decline in LVEF during extended follow-up. Candesartan during adjuvant therapy did not prevent reduction in LVEF at 2 years, but was associated with modest reduction in left ventricular end-diastolic volume and preserved global longitudinal strain. These results suggest that a broadly administered cardioprotective approach may not be required in most patients with early breast cancer without preexisting cardiovascular disease. URL: https://www.clinicaltrials.gov; Unique identifier: NCT01434134. 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: 145040-37-5Product Details 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. 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.Product Details of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem