Category: imidazoles-derivatives

peri-Substituted imidazo[1,2-a]pyridines. A new reductive elimination reaction was written by Rees, Charles W.;Smith, David I.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1987.Safety of 5-Bromoimidazo[1,2-a]pyridine This article mentions the following:

A new reductive elimination reaction of 3,5-disubstituted imidazo[1,2-a]pyridines I (R, R¹ = Br, NO₂) with N₂H₄ in hot EtOH is reported. A mechanism based on the conjugated relationship of these peri-substituents is proposed and used to explain the reported conversion of 1,3,5-trichloro-2,4,6-trinitrobenzene into 1,3-dichloro-4,6-dinitrobenzene. A variety of other 3-nitro-5-substituted imidazo[1,2-a]pyridines I (R = NO₂, R¹ = CO₂Me, CONHNH₂, CON₃, NH₂, NHCO₂Me, N₃, etc.) are described, but these could not be cyclized. The 3-amino-5-methoxycarbonyl derivative I (R = NH₂, R¹ = CO₂Me) cyclizes to the imidazoindazole II with NaOMe. In the experiment, the researchers used many compounds, for example, 5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1Safety of 5-Bromoimidazo[1,2-a]pyridine).

5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Safety of 5-Bromoimidazo[1,2-a]pyridine

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations was written by Primozic, Ines;Hrenar, Tomica;Baumann, Kresimir;Kristo, Lucija;Krizic, Ivana;Tomic, Srdanka. And the article was included in Croatica Chemica Acta in 2014.Related Products of 3012-80-4 This article mentions the following:

New mechanochem. pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quant. yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational anal. and quantum-chem. calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Related Products of 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Related Products of 3012-80-4

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.COA of Formula: C4H5N3O2 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-4-nitroimidazole (cas: 3034-41-1COA of Formula: C4H5N3O2).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. 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. COA of Formula: C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effect of temperature on the interactions between low bandgap polymer and ionic liquids was written by Attri, Pankaj;Lee, Seung-Hyun;Hwang, Sun Woo;Kim, Joong Il;Jang, Won;Kim, Young Beom;Park, Jung Ho;Kwon, Gi-Chung;Choi, Eun Ha;Kim, In Tae. And the article was included in Thermochimica Acta in 2014.Synthetic Route of C4H7ClN2 This article mentions the following:

In this paper, we have examined the effect of temperature on the interactions between imidazolium and ammonium based ionic liquids (ILs) and the low bandgap polymer (poly(2-heptadecyl-4-vinylthieno[3,4-d]thiazole) (PHVTT)). With the aim of exploring the utility of low bandgap polymers, we have carried out the interaction studies of the polymer with the ILs and investigated the behavior of polymer in the presence of ILs as the function of temperature Recently, ILs have attracted extensive attention in polymer sciences. In this work, we have studied the temperature dependent interactions between the protic IL (1-methylimidazolium chloride ([Mim]Cl) from imidazolium family) and aprotic ILs (tributylmethylammonium Me sulfate ([N₁₄₄₄][MeSO₄]) from ammonium family and 1-butyl-3-methylimidazolium chloride ([Bmim]Cl) from imidazolium family) with a low bandgap polymer. Our exptl. data of UV-vis spectroscopy, photoluminescence (PL) spectroscopy, FT-IR spectroscopy, d. (ρ) and speed of sound (u) as a function of temperature from 25 to 40° with the interval of 5°, clearly reveal that even at high temperature, [Bmim]Cl interacts strongly with the polymer as compared to other studied ILs. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Synthetic Route of C4H7ClN2).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Controlling selectivity for cycloadditions of nitrones and alkenes tethered by benzimidazoles: combining experiment and theory was written by Meng, Liping;Wang, Selina C.;Fettinger, James C.;Kurth, Mark J.;Tantillo, Dean J.. And the article was included in European Journal of Organic Chemistry in 2009.Related Products of 3012-80-4 This article mentions the following:

A combined exptl./theor. study on the effects of substituents on regio- and stereoselectivity in intramol. 1,3-dipolar cycloadditions of nitrones and alkenes tethered by benzimidazoles. By employing a large substituent at position R² or R³, complete selectivity was achieved for either the fused or bridged cycloadduct, resp. In addition, these cycloadducts were formed as single diastereomers in all of the cycloadditions examined In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Related Products of 3012-80-4).

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. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Related Products of 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic molecules for disruption of the MYC protein-protein interface was written by Jacob, Nicholas T.;Miranda, Pedro O.;Shirey, Ryan J.;Gautam, Ritika;Zhou, Bin;de Orbe Izquierdo, M. Elena;Hixon, Mark S.;Hart, Jonathan R.;Ueno, Lynn;Vogt, Peter K.;Janda, Kim D.. And the article was included in Bioorganic & Medicinal Chemistry in 2018.Synthetic Route of C6H8N2O This article mentions the following:

MYC is a key transcriptional regulator involved in cellular proliferation and has established roles in transcriptional elongation and initiation, microRNA regulation, apoptosis, and pluripotency. Despite this prevalence, functional chem. probes of MYC function at the protein level have been limited. Previously, we discovered 5a, that binds to MYC with potency and specificity, downregulates the transcriptional activities of MYC and shows efficacy in vivo. However, this scaffold posed intrinsic pharmacokinetic liabilities, namely, poor solubility that precluded biophys. interrogation. Here, we developed a screening platform based on field-effect transistor anal. (Bio-FET), surface plasmon resonance (SPR), and a microtumor formation assay to analyze a series of new compounds aimed at improving these properties. This blind SAR campaign has produced a new lead compound of significantly increased in vivo stability and solubility for a 40-fold increase in exposure. This probe represents a significant advancement that will not only enable biophys. characterization of this interaction and further SAR, but also contribute to advances in understanding of MYC biol. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Synthetic Route of C6H8N2O).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Synthetic Route of C6H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

Evaluation of lophine derivatives as chemiluminogens by a flow-injection method was written by Nakashima, Kenichiro;Yamasaki, Hiromi;Kuroda, Naotaka;Akiyama, Shuzo. And the article was included in Analytica Chimica Acta in 1995.Quality Control of 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid This article mentions the following:

A rapid and convenient method for the evaluation of lophine (2,4,5-triphenylimidazole) derivatives as to their chemiluminescence efficiency was developed by using a flow-injection technique. Standard solutions of lophine derivatives were injected into a flow line containing a carrier solution (1.5 × 10^-4 M cobalt(II) containing 0.2% hydroxylammonium chloride in 75% methanol), which was successively combined with a flow line containing 100 mM hydrogen peroxide in H₂O and a flow line containing 1.0M KOH in H₂O, and the chemiluminescence generated was monitored. Addition of hydroxylammonium chloride into a carrier solution resulted in a significant increase in chemiluminescence. Calibration graphs for eighteen derivatives were prepared and the relative chemiluminescence intensities were estimated from the slopes of these graphs. Among the derivatives, the compounds substituted by OMe at the 2- and 3-positions, and COOH, COCl, CONHNH₂ and CONHNHCO(CH₂)₄Me at the 4-position on the Ph ring at the 2-position of the imidazole skeleton showed large chemiluminescence intensities which are comparable to that of lophine. The detection limit of lophine was 72 fmol per injection at a signal-to-noise ratio of 2. In the experiment, the researchers used many compounds, for example, 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5Quality Control of 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid).

4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Quality Control of 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of Well-Defined Adenosine Diphosphate Ribose Oligomers was written by Kistemaker, Hans A. V.;Lameijer, Lucien N.;Meeuwenoord, Nico J.;Overkleeft, Herman S.;van der Marel, Gijsbert A.;Filippov, Dmitri V.. And the article was included in Angewandte Chemie, International Edition in 2015.Recommanded Product: 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

The post-translational modification of proteins that is known as ADP ribosylation (ADPr) regulates a wide variety of important biol. processes, such as DNA-damage repair and cellular metabolism This modification is also involved in carcinogenesis and the process of aging. Therefore, a better understanding of the function of ADP-ribosylation is crucial for the development of novel therapeutics. To facilitate the elucidation of the biol. of ADPr, the availability of well-defined fragments of poly(ADP-ribose) is essential. Herein we report a solid-phase synthetic approach for the preparation of ADP-ribose oligomers of exactly defined length. The methodol. is exemplified by the first reported synthesis of an ADP-ribose dimer and trimer. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Recommanded Product: 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Recommanded Product: 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Green synthesis of acetylated maize starch in different imidazolium carboxylate and choline carboxylate ionic liquids was written by Ren, Fei;Wang, Jinwei;Yu, Jinglin;Zhong, Cheng;Xie, Fengwei;Wang, Shujun. And the article was included in Carbohydrate Polymers in 2022.Recommanded Product: 79917-89-8 This article mentions the following:

This work demonstrates that acetylated maize starches (AMS) with varied degree of substitution (DS, 0.26-2.63) was synthesized in ionic liquids (ILs) (imidazolium chloride, imidazolium carboxylate and choline carboxylate) at 85°C without catalyst. The DS of AMS and reaction efficiency increased with decreasing alkyl chain length of cations or anions, while decreased as the choline cation replaced the imidazolium cation and the chloride anion replaced the acetate anion. The AMS synthesized in imidazolium-based ILs exhibited much higher hydrophobicity and thermal stability than the native starch. Rheol. properties of ILs and ATR-FTIR anal. of acetic anhydride/ILs mixtures indicated that a shorter alkyl side chain or the combination of an imidazolium cation and an acetate anion gave ILs lower viscosities and weaker interactions between acetic anhydride mols., which favored the acetylation of starch. These findings provide insights into the design of green processes to modify starch and the application of acetylated starch. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Recommanded Product: 79917-89-8).

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. 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: 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem