Category: imidazoles-derivatives

The author of 《Gold-Acetonyl Complexes: From Side-Products to Valuable Synthons》 were Gasperini, Danila; Collado, Alba; Gomez-Suarez, Adrian; Cordes, David B.; Slawin, Alexandra M. Z.; Nolan, Steven P.. And the article was published in Chemistry – A European Journal in 2015. Electric Literature of C27H38AuClN2 The author mentioned the following in the article:

A new synthetic strategy was devised giving complexes, such as [Au(IPr)(CH2COCH3)] (IPr = N,N’-bis(2,6-diisopropylphenyl)imidazol-2-ylidene). The approach capitalizes on the formation of a decomposition product observed in the synthesis of [Au(IPr)(Cl)]. A library of Au acetonyl complexes containing the most common N-heterocyclic carbene (NHC) ligands was synthesized. These acetonyl complexes are good synthons for the preparation of numerous organogold complexes. Moreover, they proved to be precatalysts in common Au(I)-catalyzed reactions. In the experimental materials used by the author, we found Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Electric Literature of C27H38AuClN2)

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
Electric Literature of C27H38AuClN2 However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Cationic heteroaromatic carbamates as acetylcholinesterase inhibitors. Synthesis and inhibitory activity of 5-, 6-, 7- and 8-carbamoyloxy derivatives of 2-substituted imidazo[1,2-a]pyridinium salts》 were Sundberg, Richard J.; Van Nguyen, Phuoc; Jiang, Songchun. And the article was published in Medicinal Chemistry Research in 1997. Formula: C8H8N2O The author mentioned the following in the article:

A series of 1-Me 5-, 6-, 7-, and 8-N,N-dimethylcarbamoyloxy derivatives of imidazo[1,2-a]pyridinium salts with varying 2-substituents (H, Me, Me2CH, Ph) was prepared The inhibitory activity against acetylcholinesterase (AChE) was determined The 5- and 8-substituted compounds are active as AChE inhibitors in the submicromolar range and show significant acute toxicity. The AChE inhibitory activity decreased in the order 5>8>7>6 as the position of substitution. Some of the compounds were also evaluated for protective effects against soman in mice. Several of the compounds have modest protective effects against 2LD50 soman. In the part of experimental materials, we found many familiar compounds, such as 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Formula: C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Formula: C8H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Antiulcer agents. 1. Gastric antisecretory and cytoprotective properties of substituted imidazo[1,2-a]pyridines》 were Kaminski, James J.; Bristol, James A.; Puchalski, Chester; Lovey, Raymond G.; Elliott, Arthur J.; Guzik, Henry; Solomon, Daniel M.; Conn, David J.; Domalski, Martin S.. And the article was published in Journal of Medicinal Chemistry in 1985. Computed Properties of C8H8N2O The author mentioned the following in the article:

The title compounds (I; R = H, OH, CHO, PhO, (un)substituted benzyloxy, PhCH2NH, etc.; R1 = H, or PhCH2CH2; R2 = H, Me, Et, CHMe2; R3 = H, Me, CO2H, CO2Et, CN, CH2CN, etc.), prepared in general by condensation of substituted 2-aminopyridines with α-halocarbonyls, were evaluated for gastric antisecretory activity in the pylorus-ligated rat and inhibition of histamine-stimulated gastric secretion in the adult dog and gastric cytoprotective activity in the rat. In the pylorus-ligated rat, I were given at 40 mg/kg i.p., at time of ligation and reduction in acid output was measured after 4 h, and in the dog I was 1st administered i.v. 0.1-5 mg/kg and reduction in the acid output relative to nondrug-treated control value in the same animal was measured. For gastric cytoprotective activity I was given orally 1-30 mg/kg 30 min before oral administration of absolute EtOH, and the effect against EtOH-induced lesions was determined after 1 h. The results show that I are not histamine (H2) receptor antagonists nor are they prostaglandin analogs, yet they exhibit both gastric antisecretory and cytoprotective properties. The mechanism of gastric antisecretory activity may involve inhibition of H+/K+-ATPase. 3-(Cyanomethyl)-2-methyl-8-(phenylmethoxy)imidazo[1,2-a]pyridine (I); R = PhCH2O, R1 = H, R2 = Me, R3 = CH2CN)(SCH 28080) [76081-98-6] was selected for clin. evaluation. Structure-activity relations are discussed. The results came from multiple reactions, including the reaction of 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Computed Properties of C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. Computed Properties of C8H8N2O In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Shelton, Kerri L.; DeBord, Michael A.; Wagers, Patrick O.; Southerland, Marie R.; Williams, Travis M.; Robishaw, Nikki K.; Shriver, Leah P.; Tessier, Claire A.; Panzner, Matthew J.; Youngs, Wiley J. published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Synthesis, anti-proliferative activity, SAR study, and preliminary in vivo toxicity study of substituted N,N’-bis(arylmethyl)benzimidazolium salts against a panel of non-small cell lung cancer cell lines》.Safety of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol The author mentioned the following in the article:

A series of N,N’-bis(arylmethyl)benzimidazolium salts have been synthesized and evaluated for their in vitro anticancer activity against select nonsmall cell lung cancer cell lines to create a structure activity relationship profile. The results indicate that hydrophobic substituents on the salts increase the overall antiproliferative activity. The data confirms that naphthylmethyl substituents at the nitrogen atoms (N1(N3)) and highly lipophilic substituents at the carbon atoms (C2 and C5(C6)) can generate benzimidazolium salts with antiproliferative activity that is comparable to that of cisplatin. The National Cancer Institute’s Developmental Therapeutics Program tested a number of synthesized compounds in their 60 human tumor cell line screen. Results were supportive of data observed in the laboratory Compounds with hydrophobic substituents have higher anticancer activity than compounds with hydrophilic substituents. The experimental part of the paper was very detailed, including the reaction process of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Safety of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Safety of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,European Journal of Organic Chemistry included an article by Zens, Anna; Bauer, Florian; Kolb, Benedikt; Mannchen, Fabian; Seubert, Philipp; Forschner, Robert; Flaig, Kim S.; Koehn, Andreas; Kunz, Doris; Laschat, Sabine. COA of Formula: C27H39ClN2. The article was titled 《Ni(NHC) Catalyzed Rearrangement of 1-Acyl-2-vinylcyclopropanes: Tackling a Mechanistic Puzzle by Combined Experimental and Computational Studies》. The information in the text is summarized as follows:

The Ni(NHC) catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes to the corresponding 4-acyl-cyclopent-1-enes is highly promising for the synthesis of keto-functionalized annelated bi- and tricyclic subunits of natural products. Therefore, we investigated the catalytic activity of Ni(NHC) complexes in the rearrangement of 1-acyl-2-vinylcyclopropanes with different ring sizes and substitution patterns. Surprising effects regarding substrate scope and stereoselectivity of the Ni(NHC) catalyzed vinylcyclopropane-cyclopentene rearrangement were observed Only vinylcyclopropanes with 1-Me, 1-Ph, 1,2-dialkyl or 2-phenyl-substitution at the vinyl moiety could be rearranged successfully. Moreover, an endo-configuration on the cyclopropane ring was required for successful rearrangement. By treatment of the vinylcyclopropanes with Rh catalysts or Lewis acids, the involvement of Lewis acid catalysis could be ruled out. In order to understand these exptl. results and to rationalize the reactivity of the Ni(NHC) complexes computational studies were performed, which provided insights into mechanistic details. In the part of experimental materials, we found many familiar compounds, such as 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0COA of Formula: C27H39ClN2)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.COA of Formula: C27H39ClN2In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of C8H8N2OOn June 1, 2020, Sekioka, Ryuichi; Honda, Shugo; Akashiba, Hiroki; Yarimizu, Junko; Mitani, Yasuyuki; Yamasaki, Shingo published an article in Bioorganic & Medicinal Chemistry. The article was 《Optimization and biological evaluation of imidazopyridine derivatives as a novel scaffold for γ-secretase modulators with oral efficacy against cognitive deficits in Alzheimer′s disease model mice》. The article mentions the following:

Gamma-secretase modulators (GSMs) selectively lower amyloid-β42 (Aβ42) and are therefore potential disease-modifying drugs for Alzheimer′s disease (AD). Here, we report the discovery of imidazopyridine derivatives as GSMs with oral activity on not only Aβ42 levels but also cognitive function. Structural optimization of the biphenyl group and pyridine-2-amide moiety of compound 1a greatly improved GSM activity and rat microsomal stability, resp. 5-{8-[(3,4′-Difluoro[1,1′-biphenyl]-4-yl)methoxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-N-methylpyridine-2-carboxamide (1o)(I) showed high in vitro potency and brain exposure, induced a robust reduction in brain Aβ42 levels, and exhibited undetectable inhibition of cytochrome P 450 enzymes. Moreover, compound 1o showed excellent efficacy against cognitive deficits in AD model mice. These findings suggest that compound 1o is a promising candidate for AD therapeutics. The results came from multiple reactions, including the reaction of 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Electric Literature of C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
Electric Literature of C8H8N2O However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Computed Properties of C9H13Cl2N3On March 1, 2009, Cariou, Renan; Gibson, Vernon C.; Tomov, Atanas K.; White, Andrew J. P. published an article in Journal of Organometallic Chemistry. The article was 《Group 4 metal complexes bearing new tridentate (NNO) ligands: Benzyl migration and formation of unusual C-C coupled products》. The article mentions the following:

Group 4 metal complexes bearing new phenoxy(benzimidazolyl)-imine, -amine and -amide ligands have been synthesized. A series of metal chloride derivatives has been prepared via treatment of MCl4(THF)2 (M = Ti, Zr, Hf) with the in situ generated sodium salt of the (benzimidazolyl)imine phenol 1. Reaction of the pro-ligand 2 with TiCl4(THF)2 afforded the corresponding complex 8 in which the amine proton remains bound to the nitrogen donor. Benzyl complexes of zirconium and hafnium were synthesized via treatment of pro-ligands 1 and 2 with M(CH2Ph)4 precursors. The complexes [NNO]M(CH2Ph)3 (6 M = Zr, 7 M = Hf) were found to undergo benzyl migration from the metal center to the imine carbon of the ligand backbone giving complexes 11 and 12; the migration follows first order kinetics. The reaction of 1 with Ti(NMe2)4 led to the formation of an unusual C-C coupled product in which a new piperazine ring has formed. Complexes 11 and 12 undergo related transformations, leading to analogous C-C coupled products which were characterized by x-ray crystallog. Deuterium labeling experiments were carried out to determine the mechanistic pathway of the reactions. Chloride and benzyl complexes 3-12 were screened as pre-catalysts for olefin polymerization The experimental process involved the reaction of [(1-Methyl-1H-benzimidazol-2-yl)methyl]amine dihydrochloride(cas: 53332-79-9Computed Properties of C9H13Cl2N3)

[(1-Methyl-1H-benzimidazol-2-yl)methyl]amine dihydrochloride(cas: 53332-79-9) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Computed Properties of C9H13Cl2N3 Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

HPLC of Formula: 258278-25-0On June 5, 2019, Han, Bo; Ma, Pengchen; Cong, Xuefeng; Chen, Hui; Zeng, Xiaoming published an article in Journal of the American Chemical Society. The article was 《Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study》. The article mentions the following:

Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodn. stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theor. mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs. In the experimental materials used by the author, we found 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0HPLC of Formula: 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.HPLC of Formula: 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《ZIF-8 Membrane Separation Performance Tuning by Vapor Phase Ligand Treatment》 was written by Eum, Kiwon; Hayashi, Mikio; De Mello, Matheus Dorneles; Xue, Feng; Kwon, Hyuk Taek; Tsapatsis, Michael. HPLC of Formula: 934-32-7This research focused onZIF membrane separation vapor phase ligand treatment; ZIF-8; ligand-induced permselectivity; membranes; metal-organic frameworks; vapor phase. The article conveys some information:

Vapor phase ligand treatment (VPLT) of 2-aminobenzimidazole (2abIm) for 2-methylimidazole (2mIm) in ZIF-8 membranes prepared by two different methods (LIPS: ligand induced permselectivation and RTD: rapid thermal deposition) results in a notable shift of the mol. level cut-off to smaller mols. establishing selectivity improvements from ca. 1.8 to 5 for O2/N2; 2.2 to 32 for CO2/CH4; 2.4 to 24 for CO2/N2; 4.8 to 140 for H2/CH4 and 5.2 to 126 for H2/N2. Stable (based on a one-week test) oxygen-selective air separation performance at ambient temperature, 7 bar(a) feed, and 1 bar(a) sweep-free permeate with a mixture separation factor of 4.5 and oxygen flux of 2.6×10-3 mol m-2 s-1 is established. LIPS and RTD membranes exhibit fast and gradual evolution upon a 2abIm-VPLT, resp., reflecting differences in their thickness and microstructure. Functional reversibility is demonstrated by showing that the original permeation properties of the VPLT-LIPS membranes can be recovered upon 2mIm-VPLT. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7HPLC of Formula: 934-32-7)

1H-Benzo[d]imidazol-2-amine(cas: 934-32-7) can be used in the hydrolysis of a choline carbonate. It was also used in the synthesis of imidazo[1,2-a]benzimidazoles.HPLC of Formula: 934-32-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Antiulcer agents. 2. Gastric antisecretory, cytoprotective, and metabolic properties of substituted imidazo[1,2-a]pyridines and analogs》 was published in Journal of Medicinal Chemistry in 1987. These research results belong to Kaminski, James J.; Hilbert, James M.; Pramanik, B. N.; Solomon, Daniel M.; Conn, David J.; Rizvi, Razia K.; Elliott, Arthur J.; Guzik, Henry; Lovey, Raymond G.. Related Products of 79707-11-2 The article mentions the following:

In search of a successor to the imidazol[1,2-a]pyridine I (X = CH, R = OCH2Ph, R1 = Me, R2 = CH2CN) (II) (Sch 28080), a compound that exhibits gastric antisecretory and cytoprotective properties, a series of imidazopyridines, e.g., I (X = CH; R = OCH2Ph; R1 = Me, NH2; R2 = Me, CH2CN, NH2) and of imidazopyrazines, e.g., I (X = N, R = OCH2Ph, R1 = Me, R2 = NH2) (III) were prepared In three of these potential successors of II, an amino group functions as a surrogate for the 3-cyanomethyl substituent of the prototype. In addition to an evaluation of the structure-activity relationships of a series of analogs of II, preliminary studies of the pharmacodynamics and metabolism of II were performed with the aid of cyano carbon labeled versions of the drug. II is well-absorbed and extensively metabolized; the major metabolite of II is the thiocyanate anion. A similar study performed on I (X = CH, R = OCH2Ph, R1 = Me, R2 = NH2) (IV), labeled at the 3-position with carbon-13 or carbon-14, revealed that IV, which has an antisecretory/cytoprotective profile comparable to that of II, is also metabolized to thiocyanate anion, although this must occur via a different mechanism. The potential sites of protonation of the pharmacol. similar IV and the structurally related imidazo[1,2-a]pyrazine III is discussed. Predictions based on charge d. and protonation product stabilities are presented. That N1 is the site of protonation in these analogs has been definitively demonstrated by x-ray crystal structure anal., which also unequivocally established the assigned imidazopyridine and imidazo[1,2-a]pyrazine ring structures.2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Related Products of 79707-11-2) was used in this study.

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Related Products of 79707-11-2 Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem