Author: Jessica.F

Benzimidazoles. III was written by Montanari, F.;Passerini, R.. And the article was included in Bollettino Scientifico della Facolta di Chimica Industriale di Bologna in 1953.Application of 83741-35-9 This article mentions the following:

2,3-(O₂N)₂C₆H₃Cl (2 g., 1 equivalent) reduced with 13.5 g. (6 equivalents) SnCl₂.2H₂O and 15 mL. concentrated HCl, and the product vacuum-distilled (113°/4 mm.) gives 2,3-(H₂N)₂C₆H₃Cl (I). Refluxing 1 equivalent I.2HCl 3 h. with 2 equivalents anhydrous HCO₂Na gives 4-chlorobenzimidazole, m. 170-1°. 2,3-(H₂N)₂C₆H₃Br gives 4-bromobenzimidazole, m. 168°. 2,3-(H₂N)₂C₆H₃OMe, m. 39-40°, gives 4-methoxybenzimidazole, m. 168°. 5-Nitro benzimidazole with SnCl₂ gives the 5-amino compound, m. 164°. 2-Nitro-6-methylbenzimidazole (15 g.) suspended in 33 mL. concentrated HCl and a little EtOH with 0.21 g. Sn yields the chlorostannate which gives 4-methyl-2-phenylbenzimidazole, m. 246°. BzH with 2,3-(H₂N)₂C₆H₃R gives the following 4-R derivatives of 2-phenylbenzimidazole: Cl, m. 227-8°; MeO, m. 214-15°; O₂N, m. 194-5°. With 3,4-(H₂N)₂C₆H₃OMe, BzH gives 5-methoxy-2-phenylbenzimidazole, m. 218-19°. By reduction of 2-nitro-2′-methylbenzanilide (from ο-nitroaniline and ο-MeC₆H₄COCl) is obtained 2-ο-tolylbenzimidazole, m. 111-12°. Likewise from the corresponding benzanilides are obtained the following benzimidazoles: 2-m-tolyl, m. 112-13°; 2-(ο-methoxyphenyl), m. 179-80°; and 2-(m-methoxyphenyl), m. 205°. 18 references In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-benzoimidazole (cas: 83741-35-9Application of 83741-35-9).

4-Bromo-1H-benzoimidazole (cas: 83741-35-9) 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. 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 83741-35-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer was written by Tanaka, Takafumi;Tanaka, Tsukushi;Tsuji, Taro;Yazaki, Ryo;Ohshima, Takashi. And the article was included in Organic Letters in 2018.Related Products of 85692-37-1 This article mentions the following:

A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center, e.g., I (X-rays single crystal structure shown), were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis. 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 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.Related Products of 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Comparative Pharmaceutical Evaluation of Candesartan and Candesartan Cilexetil: Physicochemical Properties, In Vitro Dissolution and Ex Vivo In Vivo Studies was written by Amer, Ahmed M.;Allam, Ahmed N.;Abdallah, Ossama Y.. And the article was included in AAPS PharmSciTech in 2018.Computed Properties of C33H34N6O6 This article mentions the following:

The aim of the present work is to answer the question is it possible to replace the ester prodrug candesartan cilexetil (CC) by its active metabolite candesartan (C) to bypass the in vivo variable effect of esterase enzymes. A comparative physicochem. evaluation was conducted through solubility, dissolution, and stability studies; addnl., ex vivo permeation and in vivo studies were assessed. C demonstrated higher solubility over CC at alk. pH. Moreover, dissolution testing using the pharmacopeial method showed better release profile of C even in the absence of surfactant in the testing medium. Both drugs demonstrated a slight degradation in acidic pH after short-term stability. Instead, shifting to alk. pH of 6.5 and 7.4 showed superiority of C solution stability compared to CC solution The ex vivo permeation results demonstrated that the parent compound C has a significant (P < 0.05) enhanced permeation compared to its prodrug from CC, that agreed with in vivo results in which C suspension reached significantly (P < 0.05) higher Cmax of 1.39 ± 0.59μg/mL at Tmax of 0.66 ± 0.11 h, while CC suspension reached Cmax of 0.47 ± 0.22μg/mL at Tmax of 2.00 ± 0.27 h, a lag period of 40 min is needed prior to detection of any absorbed CC in plasma. Those findings are not in agreement with the previously reported rationale on the prodrug formation owing to the poor permeability of the parent compound, suggesting the possibility of marketing the parent drug candesartan for clin. use similarly to azilsartan and its prodrug. 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: 145040-37-5Computed Properties of C33H34N6O6).

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 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.Computed Properties of C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effects of imidazo[1,2-a]benzimidazole derivatives on gastric secretion and the antiulcer action was written by Spasov, A. A.;Kovalev, G. V.;Bakumov, P. A.;Reshetov, M. E.;Anisimova, V. A.;Avdyunina, N. I.. And the article was included in Farmakologiya i Toksikologiya (Moscow) in 1990.Synthetic Route of C9H9N3 This article mentions the following:

Experiments on rats showed that of 16 studied imidazo [1,2-a] benzimidazole derivatives only the compounds with Ph at C-2 and a N-containing radical at N-9 inhibit gastric acid secretion. The binding of a methoxy group to Ph, replacement by its adamantyl, displacement of the N-containing substituent to N-1 or its substitution were found to decrease or stop the inhibiting action of these substances on gastric parietal cells. Dihydrochloride of 2-phenyl-9(β-diethylaminoethyl)imidazo[1,2-a]benzimidazole was more potent than cimetidine and omeprazole in inhibiting gastric acid secretion and pepsin output, and in exerting an antiulcer action. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Synthetic Route of C9H9N3).

2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7) 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 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.Synthetic Route of C9H9N3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A simplified synthesis of 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate was written by Wilson, Hanna. And the article was included in Journal of Labelled Compounds & Radiopharmaceuticals in 2003.Safety of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:

2-Nitro-1H-Imidazole-1-acetic acid (2,3,5,6-tetrafluorophenyl) ester was synthesized via an improved route which involves the direct coupling of 2-(2-nitroimidazol-1-yl)acetic acid with 2,3,5,6-tetrafluorophenol. This ester is an intermediate for ¹⁸F-fluorinated derivatives of 2-nitro-N-(2,3,3-trifluoropropyl)-1H-imidazole-1-acetamide or fluoroetanidazole. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Safety 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. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Safety of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A Heterogeneous Iridium Catalyst for the Hydroboration of Pyridines was written by Rodriguez, Jessica;Conley, Matthew P.. And the article was included in Organic Letters in 2022.Computed Properties of C8H8N2 This article mentions the following:

Sulfated Zr oxide (SZO) capped with silylium-like ions reacts with (cod)Ir(py)Cl (cod = 1,5-cyclooctadiene; py = pyridine) to form [Ir(cod)py][SZO] (1) and Me₃SiCl. 1 Can also be formed in reactions of phosphonium functionalized SZO and [Ir(cod)(OSi(O^tBu)₃)]₂, which forms [Ir(cod)P(^tBu)₂Ph][SZO] (2), followed by reaction with pyridine to form 1. FTIR and ¹⁵N{¹H} MAS NMR spectroscopy are consistent with coordination of pyridine in 1 to an electrophilic Ir. 1 Is moderately active in the dearomative hydroboration of pyridine. The primary product of this reaction is 1,2-dihydropyridine, which converts to the 1,4-dihydropyridine product at long reaction times. 1 Catalyzes the dearomative hydroboration of a variety of substituted pyridines and is also reactive toward pyrazines and N-methylimidazole. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Computed Properties of C8H8N2).

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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Computed Properties of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Bioreductive Markers for Hypoxic Cells: 2-Nitroimidazoles with Biotinylated 1-Substituents was written by Hodgkiss, Richard J.;Parrick, John;Porssa, Manuchehr;Stratford, Michael R. L.. And the article was included in Journal of Medicinal Chemistry in 1994.Recommanded Product: 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:

The interference by oxygen with the bioreductive metabolism and binding within cells of 2-nitroimidazoles has been used to identify hypoxic cells. Three title novel compounds, e.g. I, were synthesized with a 1-substituent containing a biotin moiety. Bound adducts of these compounds could be identified in hypoxic cells in vitro by the biotin binding proteins, avidin or streptavidin, labeled with fluorescein. The metabolism and discrimination of these compounds between well-oxygenated and hypoxic cells was evaluated by flow cytometry. Ester or amide links between the 2-nitroimidazole and the biotin were degraded in the presence of mouse serum, but a compound with a C5 hydrocarbon link was stable, and this compound was suitable for evaluation in an in vivo tumor model. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Recommanded Product: 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. 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Recommanded Product: 2-(2-Nitro-1H-imidazol-1-yl)acetic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ²-(C,S)-Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine was written by Egly, Julien;Chen, Weighang;Maisse-Francois, Aline;Bellemin-Laponnaz, Stephane;Achard, Thierry. And the article was included in European Journal of Inorganic Chemistry in 2022.Reference of 1632-83-3 This article mentions the following:

Amide synthesis is one of the most crucial transformations in chem. and biol. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcs. with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an addnl. ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η⁶-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i.e. 3c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Reference of 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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.Reference of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Asymmetric Copper(II)-Catalysed Nitroaldol (Henry) Reactions Utilizing a Chiral C₁-Symmetric Dinitrogen Ligand was written by Zhou, Yirong;Gong, Yuefa. And the article was included in European Journal of Organic Chemistry in 2011.Electric Literature of C9H8N2O This article mentions the following:

A series of stable chiral C₁-sym. dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 (I) in combination with CuCl₂·2H₂O (2.5 mol % or 5.0 mol %) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalc. products in high yields (up to 97 %) and with good enantioselectivities (up to 96 %) under mild reaction conditions. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Electric Literature of C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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. Electric Literature of C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099) was written by Basarab, Gregory S.;Hill, Pamela J.;Garner, C. Edwin;Hull, Ken;Green, Oluyinka;Sherer, Brian A.;Dangel, P. Brian;Manchester, John I.;Bist, Shanta;Hauck, Sheila;Zhou, Fei;Uria-Nickelsen, Maria;Illingworth, Ruth;Alm, Richard;Rooney, Mike;Eakin, Ann E.. And the article was included in Journal of Medicinal Chemistry in 2014.Product Details of 85692-37-1 This article mentions the following:

AZD5099 I is an antibacterial agent that entered phase 1 clin. trials targeting infections caused by Gram-pos. and fastidious Gram-neg. bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramol. hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound I showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency vs. the drug was low, and reports of clin. resistance due to alteration of the target are few. Hence, I could offer a novel treatment for serious issues of resistance to currently used antibacterials. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Product Details of 85692-37-1).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) 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 This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Product Details of 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem