Imidazoles-derivatives

Discovery of imidazolidine-2,4-dione-linked HIV protease inhibitors with activity against lopinavir-resistant mutant HIV was written by Flosi, William J.;DeGoey, David A.;Grampovnik, David J.;Chen, Hui-ju;Klein, Larry L.;Dekhtyar, Tatyana;Masse, Sherie;Marsh, Kennan C.;Mo, Hong Mei;Kempf, Dale. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

A new series of HIV protease inhibitors has been designed and synthesized based on the combination of the (R)-(hydroxyethylamino)sulfonamide isostere and the cyclic urea component of lopinavir. The series was optimized by replacing the 6-membered cyclic urea linker with an imidazolidine-2,4-dione which readily underwent N-alkylation to incorporate various methylene-linked heterocycle groups that bind favorably in site 3 of HIV protease. Significant improvements compared to lopinavir were seen in cell culture activity vs. wild-type virus (pNL4-3) and the lopinavir-resistant mutant virus A17 (generated by in vitro serial passage of HIV-1 (pNL4-3) in MT-4 cells). Select imidazolidine-2,4-dione containing PIs were also more effective at inhibiting highly resistant patient isolates Pt1 and Pt2 than lopinavir. Pharmacokinetic data collected for compounds in this series varied considerably when coadministered orally in the rat with an equal amount of ritonavir (5 mg/kg each). The AUC values ranged from 0.144 to 12.33 μg h/mL. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Permeability and selectivity of acid gases in supported conventional and novel imidazolium-based ionic liquid membranes was written by Akhmetshina, Alsu I.;Gumerova, Olesya R.;Atlaskin, Artem A.;Petukhov, Anton N.;Sazanova, Tatyana S.;Yanbikov, Nail R.;Nyuchev, Alexander V.;Razov, Evgeny N.;Vorotyntsev, Ilya V.. And the article was included in Separation and Purification Technology in 2017.Product Details of 35487-17-3 This article mentions the following:

The novel imidazolium salts based on bis(2-ethylhexyl) sulfosuccinate anion have been developed as ionic liquids (ILs) which can potentially be used as absorbents of acid gases. The transport of CO₂, H₂S, CH₄ and N₂ in a series of supported ionic liquid membranes (SILMs) with immobilized conventional (bmim[PF₆], bmim[BF₄], bmim[Tf₂N]) and novel ILs was investigated. The supported ionic liquid membrane containing 1-butyl-3-methylimidazolium bis(2-ethylhexyl) sulfosuccinate (bmim[doc]) yielded a very high H₂S solubility and, hence, H₂S/N₂ selectivity equal to 65. However, the permeability of acid gases through such a membrane had relatively low values varying in a range of 100-200 Barrer, whereas permeability for SILMs impregnated by conventional ILs achieved 565 Barrer. The most effective separation of CO₂ was observed for SILMs impregnated by bmim[BF₄] predominantly owing to solubility component of permeability. In order to estimate the stability of SILMs, the polymeric support surface properties such as free surface energy, surface topol. and roughness parameters were evaluated. Anal. of exptl. data revealed that among the tested ILs, bmim[BF₄] immobilized in porous polymeric support was more resistant to losses and determined the higher stability of membranes. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Product Details of 35487-17-3).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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. 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 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

N-Monomethylation of Amines with Methanol by Syndiotactic Poly(aminostyrene)-supported Palladium Nanoparticle Catalyst was written by Jiang, Lei;Zhang, Xiaoyan;Wang, Yinran;Guo, Fang;Hou, Zhaomin. And the article was included in Asian Journal of Organic Chemistry in 2021.Quality Control of 1-Methylbenzimidazole This article mentions the following:

Palladium nanocatalyst supported on dimethylamino-functionalized syndiotactic polystyrene (Pd@sPSNMe₂) showed high activity and selectivity for the N-monomethylation of various primary amines RNH₂ (R = Ph, cyclohexyl, 3-(morpholin-4-yl)propyl, 2-(1H-indol-3-yl)ethyl, etc.) using methanol as methylation reagent under air to prepare monomethylated amines RNH(CH₃), 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and N-methyl-1H-benzo[d]imidazole. The excellent catalytic performance could be associated with the ultrafine palladium nanoparticles and high amine-adsorbing capacity of the catalyst. The Pd@sPS-NMe₂ catalyst was highly robust, and could be easily recovered by filtration and reused more than ten times without decrease in activity and selectivity. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Quality Control of 1-Methylbenzimidazole).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Does the rising placebo response impact antihypertensive clinical trial outcomes? An analysis of data from the Food and Drug Administration 1990-2016 was written by Khan, Arif;Mar, Kaysee Fahl;Schilling, Joshua;Brown, Walter A.. And the article was included in PLoS One in 2018.Reference of 145040-37-5 This article mentions the following:

Background Recent studies show that placebo response has grown significantly over time in clin. trials for antidepressants, ADHD medications, antiepileptics, and antidiabetics. Contrary to expectations, trial outcome measures and success rates have not been impacted. This study aimed to see if this trend of increasing placebo response and stable efficacy outcome measures is unique to the conditions previously studied or if it occurs in trials for conditions with physiol.-measured symptoms, such as hypertension. Method For this reason, we evaluated the efficacy data reported in the US Food and Drug Administration Medical and Statistical reviews for 23 antihypertensive programs (32,022 patients, 63 trials, 142 treatment arms). Placebo and medication response, effect sizes, and drug-placebo differences were calculated for each treatment arm and examined over time using meta-regression. We also explored the relationship of sample size, trial duration, baseline blood pressure, and number of treatment arms to placebo/drug response and efficacy outcome measures. Results Like trials of other conditions, placebo response has risen significantly over time (R² = 0.093, p = 0.018) and effect size (R² = 0.013, p = 0.187) drug-placebo difference (R² = 0.013, p = 0.182) and success rate (134/142, 94.4%) have remained unaffected, likely due to a significant compensatory increase in antihypertensive response (R² = 0.086, p<0.001). Treatment arms are likely overpowered with sample sizes increasing over time (R² = 0.387, p<0.0001) and stable, large effect sizes (0.78 -0.37). The exploratory anal. of sample size, trial duration, baseline blood pressure, and number of treatment arms yielded mixed results unlikely to explain the pattern of placebo response and efficacy outcomes over time. The magnitude of placebo response had no relationship to effect size (p = 0.877), antihypertensive- placebo differences (p = 0.752), or p-values (p = 0.963) but was correlated with antihypertensive response (R² = 0.347, p<0.0001). Conclusions As hypothesized, this study shows that placebo response is increasing in clin. trials for hypertension without any evidence of this increase impacting trial outcomes. Attempting to control placebo response in clin. trials for hypertension may not be necessary for successful efficacy outcomes. In exploratory anal., we noted that despite finding significant relationships, none of the trial or patient characteristics we examined offered a clear explanation of the rise in placebo and stability in outcome measures over time. Collectively, these data suggest that the phenomenon of increasing placebo response and stable efficacy outcomes may be a general trend, occurring across trials for various psychiatric and medical conditions with physiol. and non-physiol. endpoints. 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: 145040-37-5Reference 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. 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 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Formulation development & evaluation of candesartan cilexetil mucoadhesive buccal films was written by Kumari, K. Prema;Malyadri, T.;Sreenivasaprasana, P.. And the article was included in European Journal of Biomedical and Pharmaceutical Sciences in 2019.Synthetic Route of C33H34N6O6 This article mentions the following:

Candesartan cilexetil useful in the tretament of hypertension having Angiotensin II receptor antagonist activity Buccoadhesive films of candesartan were prepared by solvent-casting method using novel polymers to improve the efficacy and bioavailability than the conventional formulations. The Prepared buccal films were evaluated for their weight, thickness, surface pH, swelling index, drug content uniformity, in vitro residence time, folding endurance in vitro release and permeation studies. the formulation C11 contain polyox to prepare sustained release mucoadhesive films of Candesartan as this formulation retards the release rate upto 8hrs and at the end of 8 h the release rate was found to be highest (i.e., 99.6%). Formulation C11showed good swelling, a convenient residence time and promising extended drug release, which can be selected for the development of buccal film for effective therapeutic use. The data observed from this study highlight the feasibility of the buccal route as a viable option for delivery of candesartan cilexetil. 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: 145040-37-5Synthetic Route 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 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).Synthetic Route of C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A comparison study on the properties of 1,3-dialkylimidazolium tetrafluoroborate salts prepared by halogen-free and traditional method was written by Wang, Ruifeng;Qi, Xiujuan;Liu, Shimin;He, Yude;Deng, Youquan. And the article was included in Journal of Molecular Liquids in 2016.Formula: C11H20N2 This article mentions the following:

A series of 1,3-dialkylimidazolium tetrafluoroborate salts had been prepared via one-step alkylation of N-alkylimidazole with trialkyloxonium salts and traditional two-step method, resp. The possible impurities in these ionic liquids (ILs) such as Cl^–, Br^–, Na⁺ and alkyl imidazoles were measured. Detailed characterizations of two approaches in the ILs properties and performances such as spectroscopic properties, phase behavior, viscosity, refractive index, and electrochem. properties were systemically conducted. The obtained results showed that the variety of synthesized methods resulted in the distinct changes in physicochem. properties for the same IL. Therein, the comparison of spectroscopic properties and phase behaviors for the employed ILs were emphasized. Furthermore, in most cases, the ILs prepared by traditional two-step possessed the higher viscosity, lower refractive index as well as lower ionic conductivity than that of ILs prepared by one-step. It was worth noting that the 1-decyl-3-ethylimidazolium tetrafluoroborate ([DEIm]BF₄) prepared with the traditional and trialkyloxonium methods resp. exhibited distinctly different phase and fluorescence behaviors. The reason might be attributed to the significant improvement on the purities of ILs by the one-step strategy. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Formula: C11H20N2).

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. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Formula: C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Discovery of 1-Methyl-1H-imidazole Derivatives as Potent Jak2 Inhibitors was written by Su, Qibin;Ioannidis, Stephanos;Chuaqui, Claudio;Almeida, Lynsie;Alimzhanov, Marat;Bebernitz, Geraldine;Bell, Kirsten;Block, Michael;Howard, Tina;Huang, Shan;Huszar, Dennis;Read, Jon A.;Rivard Costa, Caroline;Shi, Jie;Su, Mei;Ye, Minwei;Zinda, Michael. And the article was included in Journal of Medicinal Chemistry in 2014.Formula: C4H5N3O2 This article mentions the following:

Structure based design, synthesis, and biol. evaluation of a novel series of 1-methyl-1H-imidazole, as potent Jak2 inhibitors to modulate the Jak/STAT pathway, are described. Using the C-ring fragment from our first clin. candidate AZD1480 (I), optimization of the series led to the discovery of compound II, a potent, orally bioavailable Jak2 inhibitor. Compound II displayed a high level of cellular activity in hematopoietic cell lines harboring the V617F mutation and in murine BaF3 TEL-Jak2 cells. Compound II demonstrated significant tumor growth inhibition in a UKE-1 xenograft model within a well-tolerated dose range. 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. 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.Formula: C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and biological activity of N-acylmethyl derivatives of 9H-2,3-dihydroimidazo- and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles and their reduction products was written by Anisimova, V. A.;Tolpygin, I. E.;Spasov, A. A.;Kosolapov, V. A.;Stepanov, A. V.;Kucheryavenko, A. F.. And the article was included in Pharmaceutical Chemistry Journal in 2006.Recommanded Product: 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole This article mentions the following:

A series of N-acylmethyl derivatives of 9H-2,3-dihydroimidazo- and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles and products of their reduction has been synthesized and their pharmacol. properties have been studied. Most of the synthesized substances possess weak antioxidant activity. At the same time, they exhibit pronounced antiaggregant and hemorheol. properties, possess spasmolytic activity, and influence the blood glucose level. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Recommanded Product: 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Pharmacophore modeling and 3D-QSAR studies on substituted benzothiazole/benzimidazole analogues as DHFR inhibitors with antimycobacterial activity was written by Priyadarsini, R.;Tharani, C. B.;Suganya, Sathya;Kavitha, S.. And the article was included in International Journal of Pharma Sciences and Research in 2012.Safety of 7-Methyl-1H-benzo[d]imidazole This article mentions the following:

The resurgence of tuberculosis and the emergence of multidrug-resistant strains of Mycobacteria drugs has propelled the development of new structural classes of antitubercular agents. The present study was undertaken to investigate the opportunities which the enzyme dihydrofolate reductase, a promising drug target for treatment of Mycobacterial infections offers for the development of new TB drugs. Pharmacophore models were established by using the HipHop and HypoGen algorithms implemented in the Catalyst software package. The best quant. pharmacophore model, consisted of two hydrogen bond acceptor, a hydrophobic aliphatic and a ring aromatic feature which has the highest correlation coefficient (0.93), as well as enrichment factor of 1.75 and Goodness of hit score of 0.73. Based on the pharmacophore model some leads were optimized and some of its derivatives were synthesized and analyzed by following QSAR studies. About 25 compounds of substituted benzothiazole/benzimidazole derivatives were synthesized as potent DHFR inhibitors and screened for antimycobacterial activity. To further explore the structure-activity relationships of all newly synthesized compounds, 3D-QSAR analyses were developed. MFA studies were performed with the QSAR module of Cerius2 using genetic partial least squares (G/PLS) algorithm. The predictive ability of the developed model was assessed using a training set of 25 and a test set of 5 compounds (r2pred = 0.924). The analyzed MFA model demonstrated a good fit, having r2 value of 0.868 and cross validated coefficient r2cv value of 0.771. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Safety of 7-Methyl-1H-benzo[d]imidazole).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

NMR Characterization of Hydrate and Aldehyde Forms of Imidazole-2-carboxaldehyde and Derivatives was written by Lazaro Martinez, Juan Manuel;Romasanta, Pablo Nicolas;Chattah, Ana Karina;Buldain, Graciela Yolanda. And the article was included in Journal of Organic Chemistry in 2010.HPLC of Formula: 22600-77-7 This article mentions the following:

The existence and stability of the aldehyde-hydrate form of imidazole-2-carboxaldehyde (4) were studied using FTIR together with solution- and solid-state NMR experiments The results allowed us to conclude that the hydrate form was stable and precipitated at pH = 8.0 and that the aldehyde form was isolated at pH = 6.5 and 9.5. Moreover, the presence of the aldehyde-hydrate form was studied through NMR experiments in D₂O at both alk. and acidic pH. In addition, the tautomeric forms of the 2-substituted imidazole compounds were also analyzed to investigate the influence of the hybridization on the carbon adjacent to the imidazole ring, by ¹³C NMR in DMSO-d₆, acetone-d₆, and CDCl₃. The presence of the syn- and anti-isomers of oxime 8 obtained from 4 were characterized by solid-state NMR and variable-temperature NMR experiments in acetone-d₆. In the experiment, the researchers used many compounds, for example, (1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7HPLC of Formula: 22600-77-7).

(1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7) 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).HPLC of Formula: 22600-77-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem