Category: imidazoles-derivatives

Adjacent lone pair (ALP) effects in heteroaromatic systems. 2. Isotope exchange of ring hydrogens in nitro- and fluoroimidazoles was written by Takeuchi, Yoshio;Kirk, Kenneth L.;Cohen, Louis A.. And the article was included in Journal of Organic Chemistry in 1978.Recommanded Product: 3034-41-1 This article mentions the following:

The ring protons of nitro- and fluoroimidazoles (and their N-Me derivatives) undergo base-catalyzed exchange in D₂O by a combination of carbanion (C) and ylide (Y) pathways, which involve proton abstraction from the neutral imidazole species and from the imidazolium ion, resp. In 4-substituted imidazoles, C exchange occurs more readily at C-5 than at C-2, log k_C correlating with 蟽_o掳 for the NH- and with 蟽_p掳 for the N-Me series. For 1-methyl-4-nitroimidazole, t_1/2 = 2 min at C-5 (50掳, 0.2 N NaOD). In 1-methyl-5-X-imidazoles, exchange at C-4 occurs only via the Y pathway, carbanion formation in the neutral species being retarded by the adjacent lone pair (ALP) effect at N-3. The same effect is seen in the lack of C exchange at C-4 in 1-methylimidazoles. The ALP effect is considerably weaker or nonexistent at C-2. Most exchanges across the ring show correlations of log k with 蟼_m掳. 4-Alkylimidazoles (but not 1,4-dialkylimidazoles) show enhanced C exchange at C-5, which may result from the existence of a trace concentration of the ketimine tautomer. Enhanced exchange at C-5 in 2-fluorohistidine is ascribed to a combination of the ketimine effect, C exchange involving catalysis by OH and intramol. general-base catalysis by the side-chain primary-amine function. The use of buffer catalysis for the T labeling of poorly reactive imidazoles is described. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 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.Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The mutagenic action of nitroimidazoles. IV. A comparison of the mutagenic action of several nitroimidazoles and some imidazoles was written by Voogd, C. E.;Van der Stel, J. J.;Jacobs, J. J. J. A. A.. And the article was included in Mutation Research, Genetic Toxicology Testing in 1979.COA of Formula: C4H5N3O2 This article mentions the following:

When tested with Klebsiella聽pneumoniae and (or) Salmonella聽typhimurium, 31 of 33 tested nitroimidazoles were mutagenic, whereas of 18 other tested imidazoles without a nitro group, only 2 were mutagenic. Several of the substances tested for mutagenicity had antimicrobial action, but no direct relation between antimicrobial action, growth inhibition, and mutagenicity was observed A relation between the chem. structure and mutagenic action was observed for nitroimidazoles of a more complex chem. structure. 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. 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. 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

Syntheses of 伪,尾-unsaturated ketones starting from vinylic and allylic Grignard reagents via 2-imidazolylmethanol intermediates was written by Hayakawa, Satoshi;Michiue, Toru;Okamoto, Masao;Hatakeyama, Shoko;Ohta, Shunsaku. And the article was included in Heterocycles in 1988.Recommanded Product: 85692-37-1 This article mentions the following:

The title unsaturated ketones, e.g., E-RCOCH:CHR¹ [I; R = R¹ = Ph; R = Me(CH₂)₅, Me₂C:CHCH₂CH₂CHMeCH₂, R¹ = Me] were prepared from acylimidazoles II and R¹CH:CHBr (III). Thus, Grignard reaction of II and III gave 92-100% imidazolylmethanols IV. Quaternization of IV with Me₂SO₄ followed by elimination with K₂CO₃ gave 87-90% I. Similarly, Grignard reactions of II [R = Me(CH₂)₅, cyclohexyl, Ph] with R²CH:CHCH₂Cl (R² = H, Me, Ph) gave hydroxyimidazoles V which were cleaved to give RCOCHR²CH:CH₂. Acidic isomerization gave RCOCR²:CHMe. This methodol. was used to prepare (卤)-(ar)-turmerone 4-MeC₆H₄CHMeCH₂COCH:CMe₂ in 5 steps from II (R = Me), p-MeC₆H₄CHO, and CH₂:CMeCH₂Cl. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Recommanded Product: 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Recommanded Product: 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The infrared spectra of some simple benzimidazoles was written by Morgan, K. J.. And the article was included in Journal of the Chemical Society in 1961.Related Products of 4887-83-6 This article mentions the following:

The spectra of solid specimens of the simple alkyl and perfluoroalkylbenzimidazoles are characterized by a series of strong, broad bands in the region 2400-3200 cm.^-1 They show no band in the region normally associated with the simple N-H stretching frequency. The alkyl and perfluoroalkyl groups are 2-Me, Et, 2-Pr, 2-iso-Pr, 4-Me, 5-Me, 2,5-Me₂, 2-CF₃, 2-C₂F₅, 2-C₃F₇, 4-CF₃, 5-CF₃, 2-Me-4-CF₃, 4-Me-2-CF₃, 4-Me-₂-Pr, 2,4-(CF₃)₂, 2,5-(CF₃)₂, 2-Me-4,5-(CF₃)₂ 2,4,5-(CF₃聽₃, 5-MeO-2-CF₃, 4,5,6,7-F₄-2-CF₃. Strong bands near 2400-3200 cm.^-1 are ascribed to a strong H bond of the type N-H. . .N, showing proton transfer. The position of the N-H bands of the spectra of solutions of benzimidazoles is similar to that found for pyrroles and indoles. The bands show typical displacements when tetrachloroethylene replaces CH₂Cl₂ as solvent. Small increases in the frequency of the alkyl derivatives and large decreases in frequency of the perfluoroalkyl compounds diminish as the orientation of substitution varies 2 > 4 鈮?5. These shifts are mainly due to induction, and there is little H bonding to adjacent F atoms. Compounds with perfluoralkyl substituents show more intense absorption, giving higher values of extinction coefficients and broader bands. Spectra of perimidine, 2-methyl-, 2-ethyl-, and 2-propylperimidine show broad banded absorption from 2400 to 3200 cm.^-1 In solution spectra these bonded IV-H bands are replaced by sharp bands near 3400 cm.^-1 Benzimi- dazole-2-acetic acid and difluoroacetic acid have spectra indicating a strongly bonded carbonyl group and discrete OH and NH groups. In 尾-(2-benzimidazolyl)propionic acid the carbonyl is replaced by a broad band at 1550 cm.^-1 and the C-O stretching frequency is displaced to 1410 cm.^-1 This compound is regarded as zwitterionic. 2-Benzimidazolecarboxylic acid has a bonded carbonyl group but shows no discrete OH or amino bonds. 5-Trifluoromethyl-2-benzimidazolecarboxylic acid is similar, and a low carbonyl frequency suggests that the 4-trifluoromethyl analog is best written as a nonbonded compound In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Related Products of 4887-83-6).

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) 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.Related Products of 4887-83-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nitrogen dioxide-catalyzed oxidative bromination of benzenes and naphthalines with electron-donating substituents at room temperature was written by Ren, Yun-lai;Wang, Qian;Tian, Xin-zhe;Wang, Bin-yu;Wang, Pei. And the article was included in Fenzi Cuihua in 2014.Product Details of 25676-75-9 This article mentions the following:

Oxidative bromination of benzenes and naphthalines with electron-donating substituents was investigated by using 8.2% nitrogen dioxide as the catalyst, the residual oxygen in the reaction tube as the oxidant, and mol. bromine as the brominating reagent at room temperature The used heavy metal waste-free catalyst can be easily removed from the products and scarcely stains the final products. But a small amount of byproduct from the nitration of the benzene ring was observed, which led to the consumption of nitrogen dioxide. The reaction is highly atom economic, and a majority of bromine atoms in bromine source were transferred to the bromination products. The bromination was controllable: mono- and di-bromination products were controllably obtained by changing the loading amount of the brominating reagent. Preliminary mechanistic investigation suggests that the bromination firstly undergoes the reaction between mol. bromine and aromatic ring to give aryl bromide and HBr, which is followed by oxygenation of the resulting bromine hydride to form the reactive bromine under the catalysis of the catalytic species. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Product Details of 25676-75-9).

4-Bromo-1-methylimidazole (cas: 25676-75-9) 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.Product Details of 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Efficacy and safety observation of candesartan cilexetil combined with atorvastatin in treatment of hypertension complicated with paroxysmal atrial fibrillation was written by Xue, Chunyan;Quan, Ruidong. And the article was included in Guizhou Yiyao in 2021.Product Details of 145040-37-5 This article mentions the following:

Objective: To investigate the efficacy and safety of candesartan cilexetil combined with atorvastatin in the treatment of hypertension complicated with paroxysmal atrial fibrillation. Methods: In this study, 94 patients with hypertension and paroxysmal atrial fibrillation diagnosed in our hospital were selected as the research objects, and they were randomly divided into the combination group and the routine group, with 47 cases in each group. The combination group was given candesartan cilexetil combined with atorvastatin, and the routine group was given candesartan cilexetil combined with nifedipine. In this study, blood pressure, atrial fibrillation attack, left atrial diameter, and serum levels of brain natriuretic peptide (BNP) and matrix metalloproteinase 2 (MMP-2) were observed before and after treatment. Results: The expression levels of MMP-2 and BNP, as well as the levels of hs-CRP, IL-6 and blood pressure in the combined group were significantly lower than those in the conventional group (P < 0.05). Conclusion: Candesartan cilexetil combined with atorvastatin in the treatment of hypertension complicated with paroxysmal atrial fibrillation could reduce blood pressure and atrial fibrillation episodes, reverse atrial remodeling, and improve inflammatory state. 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. 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. 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. Product Details of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Three dimensional macroporous hydroxyapatite/chitosan foam-supported polymer micelles for enhanced oral delivery of poorly soluble drugs was written by Zhang, Yanzhuo;Dong, Kai;Wang, Fang;Wang, Hongtao;Wang, Jing;Jiang, Ziqiu;Diao, Shuai. And the article was included in Colloids and Surfaces, B: Biointerfaces in 2018.Electric Literature of C33H34N6O6 This article mentions the following:

In the current study, a novel three-dimensional macroporous hydroxyapatite/ chitosan foam (HA/CS)-supported polymer micelle (PM/HA/CS) was developed, and its potential as an oral drug delivery system to enhance the solubility and oral bioavailability of poorly soluble compounds was systemically studied. Candesartan cilexetil (CC) was selected as a poorly soluble model drug. Firstly, HA/CS foam was synthesized using a wet chem. co-precipitation approach and poly-(Me methacrylate) colloidal crystals as a macropore template. Subsequently, the CC-loaded polymer micelles were efficiently encapsulated into the macropores of the HA/CS foam and freeze-dried to produce powdery CC-loaded PM/HA/CS composites (CC-PM/HA/CS). The resulting CC-PM/HA/CS particles were then characterized in terms of porous structure, morphol., angle of repose, crystallinity, drug loading, dissolution profiles, and phys. stability. Differential scanning calorimetry (DSC) anal. confirmed that CC-PM/HA/CS was present in an amorphous form and has an excellent phys. stability. Under both simulated gastric and intestinal conditions, the aqueous solubility and dissolution rate of the PM/HA/CS-based CC formulation were significantly increased compared with the pure drug powder. In addition, PM/HA/CS is almost completely non-cytotoxic. The PM/HA/CS-based CC formulation produced approx. 1.9-fold increased bioavailability when compared to the marketed tablets (Blopress) administered to fasted Sprague-Dawley rats. On the whole, PM/HA/CS benefits from the advantages of three dimensional macroporous HA/CS foam and polymer micelles, and exhibits great potential as a drug delivery system for increasing the solubility and oral bioavailability of a poorly soluble compound, like CC. 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: 145040-37-5Electric Literature 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. 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.Electric Literature of C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Development of a novel gastric process simulation model: the successful assessment of bioequivalence and bioinequivalence of a biopharmaceutics classification system class II weak acid drug was written by Zenda, Naoki;Tagami, Tatsuaki;Ozeki, Tetsuya. And the article was included in Biological & Pharmaceutical Bulletin in 2022.Application of 145040-37-5 This article mentions the following:

Bioequivalence has been assessed using in vitro dissolution testing, such as in vivo predictive dissolution methodol. However, the assessment of bioequivalence should be performed carefully, considering the effect of the in vivo environment and according to the properties of the drug. The gastric emptying process is a key factor for the assessment of biopharmaceutics classification system class II (BCS class IIa) drugs with acidic properties since they cannot dissolve in the acidic stomach, but do dissolve in the small intestine (SI). The disintegration of a tablet in the stomach affects the distribution/dissolution in the SI due to the difference in the gastric emptying step, which in turn is a result of the varying formulation of the drugs. In this study, we used the reported dynamic pH change method and a novel gastric process simulation (GPS) model, which can compare the gastric emptying of particular-sized drug particles. The in vitro results were compared to clin. data using bioequivalent and bioinequivalent products of candesartan cilexetil. It was revealed that the dynamic pH change method was inappropriate, whereas the amount of filtered drug in GPS studies with 20 and 50 渭m pore size filters could reflect the clin. results of all products. The evaluation of the gastric emptying process of drug particles less than 50 渭m enabled us to assess the bioequivalence because they probably caused the difference in the distribution in the SI. This study demonstrated the utility of the GPS model for the assessment of bioequivalence of BCS class IIa drugs. 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: 145040-37-5Application 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. 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. Application of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Energies of isomerization in nitro derivatives of diazole was written by Lebedev, Vyacheslav P.;Matyushin, Yuriy N.;Miroshnichenko, Evgeniy A.;Konkova, Tatyana S.;Vorobev, Aleksei B.;Inozemtsev, Yaroslav O.. And the article was included in International Annual Conference of ICT in 2008.Formula: C4H5N3O2 This article mentions the following:

Energy of combustion of nitro derivatives of pyrazole and imidazole are measured. The energy of isomerization is estimated as the difference between enthalpies of formation of corresponding isomers. The influence of number, place of connection and chem. nature of substituents on energy of isomerization is considered. The obtained exptl. magnitudes will essentially fill up a database on enthalpies of formation and energies of isomerization of heterocyclic aromatic five-membered rings. These data are necessary for the further development of calculated methods that will allow purposeful search of structures with the set energetic properties. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Formula: C4H5N3O2).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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鈥揅6) is higher than in water and generally decreases with a 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.Formula: C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Amino acids. I. Preparation and properties of glycocyamidine was written by McKay, A. F.;Braun, R. O.;Hatton, W. G.. And the article was included in Canadian Journal of Chemistry in 1954.COA of Formula: C6H8N2O2S This article mentions the following:

Free guanidine with Et glycinate gave 29% glycocyamidine (I). Heating guanidine carbonate with glycine produced no I, but 55% guanidinoacetic acid (II). This was esterified with EtOH by azeotropic removal of H₂O by C₆H₆ from an alc. HCl solution to produce Et guanidinoacetate-HCl (III); picrate, m. 189.5-90.5掳. Aqueous III treated with Amberlite IRA-400 and the resulting solution evaporated gave a mixture of I (identified as its picrate, m. 214.5-15.5掳) and II. I was nitrated in Ac₂O-HNO₃ to glycocyamidine nitrate, m. 145掳 (from EtOH). I and II may be separated and identified by paper chromatog. with BuOH-H₂O-HOAc (4.2:4.2:1) as eluent. In the experiment, the researchers used many compounds, for example, Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8COA of Formula: C6H8N2O2S).

Ethyl 2-mercapto-1H-imidazole-4-carboxylate (cas: 64038-64-8) 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 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).COA of Formula: C6H8N2O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem