Month: February 2023

Selection, synthesis, and structure-activity relationship of tetrahydropyrido[4,3-d]pyrimidine-2,4-diones as human GnRH receptor antagonists was written by Lanier, Marion C.;Feher, Miklos;Ashweek, Neil J.;Loweth, Colin J.;Rueter, Jaimie K.;Slee, Deborah H.;Williams, John P.;Zhu, Yun-Fei;Sullivan, Susan K.;Brown, Michael S.. And the article was included in Bioorganic & Medicinal Chemistry in 2007.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

Tetrahydropyrido[4,3-d]pyrimidine-2,4-diones are prepared as potential human gonadotropin-releasing hormone receptor (hGnHR) antagonists; the choice of the tetrahydropyridopyrimidine core for hGnHR antagonists was determined computionally, with the highest scoring templates used for the preparation of potential hGnHR antagonists. Virtual templates were tested using three computational methods; the outputs of the methods were combined to yield a consensus score which is used to order the templates. The 5% of templates which scored most highly were further evaluated in silico and assessed for novelty and synthetic accessibility. After two rounds of optimization, tetrahydropyrido[4,3-d]pyrimidine-2,4-diones such as the trifluoroacetate salts of I (R = 4-Cl-2-MeC₆H₃CH₂, 2,4-Me₂C₆H₃) are prepared with K_i values for inhibition of the human gonadotropin-releasing hormone receptor of < 10 nM. 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. 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. 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

Preparation of 1-methyl-2,4,5-trinitroimidazole from derivatives of 1-methylimidazole and its oxidation under nitration conditions was written by Lian, Peng-Bao;Chen, Jian;Chen, Li-Zhen;Zhao, Chong-Yang;Wang, Jian-Long;Shen, Fen-Fen. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2020.Product Details of 3034-41-1 This article mentions the following:

1-Methylimidazole, 1-methyl-4-nitroimidazole, 1-methyl-5-nitroimidazole, or 1-methyl-4,5-dinitroimidazole gave a mixture of 1-methyl-4,5-dinitroimidazole and 1-methyl-2,4,5-trinitroimidazole under the volume ratio of HNO₃ to H₂SO₄ of 1:3 at 80° temperature for 2.5 h, and the highest unisolated yield of 1-methyl-2,4,5-trinitroimidazole was 2.4%. 1-Methyl-2,4,5-trinitroimidazole was prepared from 1-methyl-2-nitroimidazole, 1-methyl-2,4-dinitroimidazole, or 1-methyl-2,5-dinitroimidazole under the same conditions, and the yields were 65, 76, and 82%, resp. However, when the ratio of HNO₃ to H₂SO₄ was 1:5 and reaction was carried out at 120° for 2.5 h, only 1-methyl-4,5-dinitroimidazole was obtained from 1-methylimidazole, 1-methyl-4-nitroimidazole, or 1-methyl- 5-nitroimidazole in yields 43, 64, and 81%, resp. 1-Methyl-2-nitroimidazole, 1-methyl-2,4-dinitroimidazole, or 1-methyl- 2,5-dinitroimidazole gave 1-methylimidazolidine-2,4,5-trione under the same conditions, the yields were 61, 63, and 65%, resp. Meanwhile, 1-methylimidazolidine-2,4,5-trione was obtained from 1-methyl-2,4,5-trinitroimidazole. Under strong nitration conditions, the nitro group at the C-2 position is a key substituent to promote oxidation of the imidazole ring. The possible reaction mechanism for the formation of 1-methylimidazolidine-2,4,5-trione from 1-methyl-2,4,5-trinitroimidazole is given. The structure of 1-methylimidazolidine-2,4,5-trione was further confirmed by single crystal X-ray diffraction. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Product Details of 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Product Details of 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of Hetaryl-Substituted Asymmetric Porphyrins and Their Affinity to SARS-CoV-2 Helicase was written by Syrbu, S. A.;Kiselev, A. N.;Lebedev, M. A.;Gubarev, Yu. A.;Yurina, E. S.;Lebedeva, N. Sh.. And the article was included in Russian Journal of General Chemistry in 2021.Category: imidazoles-derivatives This article mentions the following:

Novel porphyrin compounds containing benzothiazole, benzoxazole, and benzimidazole moieties have been prepared and their structures have been confirmed. Mol. docking of non-sym. hetaryl-substituted porphyrins and chlorin e6 with SARS-CoV-2 helicase has been carried out. The affinity of hetaryl-substituted porphyrins to this protein has been found significantly higher than that of the drugs approved by the FDA and chlorin e6. The structure of the complexes of SARS-CoV-2 helicase with the considered macroheterocyclic compounds has been analyzed. Possible ways to inhibit and photoinactivate SARS-CoV helicase have been suggested basing on the localization of porphyrins and chlorin e6 in the helicase domains. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Category: imidazoles-derivatives).

1-Methylbenzimidazole (cas: 1632-83-3) 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 Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Formulation and evaluation of candesartan cilexetil loaded solid lipid nanoparticles with improved bioavailability was written by Bagul, U. S.;Tagalpallewar, A. A.;Kshirsagar, A. A.. And the article was included in International Journal of Pharmaceutical Sciences and Research in 2022.Recommanded Product: 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 This article mentions the following:

In this present work, BCS class II Candesartan celexitil, as an angiotensin receptor blocker used mainly for the treatment of high blood pressure and congestive heart failure, was successfully loaded in the solid lipid nanoparticles (SLNs) by using hot high-speed homogenization method. The SLN formulations were prepared and optimized by Box Benhken design study. The SLN was characterized by Nanophox size analyzer and Delsa nano C zetameter. The SLN was also evaluated for particle size, zeta potential, entrapment efficiency, drug loading, surface morphol., and in-vitro dissolution study. The average particle size, zeta potential, percentage entrapment efficiency, and drug loading were found to be 177nm, -8.23 mV, 95.72%, and 8.23%, resp. The dissolution study of SLN showed 92.07% released in six hours compared to 46.89% release from the pure drug, which indicates a significant improvement in the bioavailability. The release of the drug from SLN showed zero-order kinetics. The stability study was also carried out and found to be stable after three months. 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: 145040-37-5Recommanded Product: 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).

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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Recommanded Product: 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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adsorption and purification of baicalin from Scutellaria baicalensis georgi extract by Ionic liquids (ILs) grafted silica was written by Fan, Yunchang;Wu, Di;Zhang, Sheli. And the article was included in Molecules in 2021.Recommanded Product: 79917-89-8 This article mentions the following:

Baicalin which has multiple biol. activities is the main active component of the root of Scutellaria baicalensis Georgi (SBG). Although its isolation and purification by adsorption methods have aroused much interest of the scientific community, it suffered from the poor selectivity of the adsorbents. In this work, an environmentally benign method was developed to prepare ionic liquids (ILs) grafted silica by using IL 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([C₂mim]NTf₂) and ethanol as reaction media. The IL 1-propyl-3-methylimidazolium chloride ([C₃mim]Cl) grafted silica ([C₃mim]+Cl-@SiO₂) was used to adsorb and purify baicalin from the root extract of Scutellaria baicalensis Georgi (SBG). Exptl. results indicated that the adsorption equilibrium can be quickly achieved (within 10 min). The adsorption behavior of [C₃mim]+Cl-@SiO₂ for baicalin was in good agreement with Langmuir and Freundlich models and the adsorption was a physisorption process as suggested by Dubinin-Radushkevich model. Compared with com. resins, [C₃mim]+Cl-@SiO₂ showed the strongest adsorption ability and highest selectivity. After desorption and crystallization, a purity of baicalin as high as 96.5% could be obtained. These results indicated that the ILs grafted silica materials were promising adsorbents for the adsorption and purification of baicalin and showed huge potential in the purification of other bioactive compounds from natural sources. 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. 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.Recommanded Product: 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Iodine-catalyzed oxidative functionalization of purines with (thio)ethers or methylarenes for the synthesis of purin-8-one analogues was written by Zhuge, Juanping;Jiang, Ziyang;Jiang, Wei;Histand, Gary;Lin, Dongen. And the article was included in Organic & Biomolecular Chemistry in 2021.Name: 1-Methylbenzimidazole This article mentions the following:

An efficient oxidative functionalization of purine-like substrates I (R = Et, Bn; R¹ = H, Cl; R² = OMe, Cl) with (thio)ethers such as oxolane, oxane, thiolane, etc. or methylarenes such as methylbenzene, 1,4-dimethylbenzene, ethylbenzene, etc. under mild conditions is described. Using I₂ as the catalyst, and TBHP as the oxidant, this protocol provides a valuable synthetic tool for the assembly of a wide range of 9-alkyl(benzyl)purin-8-one derivatives II (R³ = Bn, oxolan-2-yl, thiolan-2-yl, etc.) with high atom- and step-economy and exceptional functional group tolerance. 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. 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.Name: 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A large-scale study of ionic liquids employed in chemistry and energy research to reveal cytotoxicity mechanisms and to develop a safe design guide was written by Dzhemileva, Lilya U.;D’yakonov, Vladimir A.;Seitkalieva, Marina M.;Kulikovskaya, Natalia S.;Egorova, Ksenia S.;Ananikov, Valentine P.. And the article was included in Green Chemistry in 2021.Category: imidazoles-derivatives This article mentions the following:

Device-level applications of organic electrolytes unavoidably imply extensive contact with the environment. Despite their excellent scientific potential, ionic liquids (ILs) cannot be approved for practical usage until their life cycle and impact on the environment are assessed. In this work, we carried out the first large-scale study on the mechanisms of the cytotoxic action of various classes of ionic liquids, including imidazolium, pyridinium, pyrrolidinium, ammonium, and cholinium ILs (25 in total). We determined the biol. effect of these ILs in seven cell lines of various origins (HEK293 (human embryonic kidney), U937 (human myeloid leukemia), Jurkat (human T-cell leukemia), HL60 (human acute promyelocytic leukemia), K562 (human chronic myelogenous leukemia), A549 (human alveolar adenocarcinoma), and A2780 (human ovarian carcinoma)). The induction of apoptosis in cells upon treatment with the majority of the ILs tested was subsequently demonstrated. The new data suggest that ILs trigger the mitochondrial pathway of apoptosis due to the dissipation of the mitochondrial membrane potential and release of cytochrome c from mitochondria into the cytoplasm. The obtained results corroborate the earlier reported data on the cytotoxic effects of ILs, providing new insight into the detailed mechanisms of IL cytotoxicity. In addition, the first illustrative guide to be employed for designing ILs with targeted biol. activity is compiled. As a possible link between the electrochem. behavior of ILs and their biol. activity, the relationship between IL cytotoxicity and the electrophoretic mobility of IL cations is assessed. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Category: imidazoles-derivatives).

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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Feasibility and physiological relevance of designing highly potent aminopeptidase-sparing leukotriene A4 hydrolase inhibitors was written by Numao, Shin;Hasler, Franziska;Laguerre, Claire;Srinivas, Honnappa;Wack, Nathalie;Jager, Petra;Schmid, Andres;Osmont, Arnaud;Rothlisberger, Patrik;Houguenade, Jeremy;Bergsdorf, Christian;Dawson, Janet;Carte, Nathalie;Hofmann, Andreas;Markert, Christian;Hardaker, Liz;Billich, Andreas;Wolf, Romain M.;Penno, Carlos A.;Bollbuck, Birgit;Miltz, Wolfgang;Rohn, Till A.. And the article was included in Scientific Reports in 2017.SDS of cas: 25676-75-9 This article mentions the following:

Leukotriene A4 Hydrolase (LTA4H) is a bifunctional zinc metalloenzyme that comprises both epoxide hydrolase and aminopeptidase activity, exerted by two overlapping catalytic sites. The epoxide hydrolase function of the enzyme catalyzes the biosynthesis of the pro-inflammatory lipid mediator leukotriene (LT) B4. Recent literature suggests that the aminopeptidase function of LTA4H is responsible for degradation of the tripeptide Pro-Gly-Pro (PGP) for which neutrophil chemotactic activity has been postulated. It has been speculated that the design of epoxide hydrolase selective LTA4H inhibitors that spare the aminopeptidase pocket may therefore lead to more efficacious anti-inflammatory drugs. In this study, we conducted a high throughput screen (HTS) for LTA4H inhibitors and attempted to rationally design compounds that would spare the PGP degrading function. While we were able to identify compounds with preference for the epoxide hydrolase function, absolute selectivity was not achievable for highly potent compounds In order to assess the relevance of designing such aminopeptidase-sparing LTA4H inhibitors, we studied the role of PGP in inducing inflammation in different settings in wild type and LTA4H deficient (LTA4H KO) animals but could not confirm its chemotactic potential. Attempting to design highly potent epoxide hydrolase selective LTA4H inhibitors, therefore seems to be neither feasible nor relevant. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9SDS of cas: 25676-75-9).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electron transfer induced decomposition in potassium-nitroimidazoles collisions: an experimental and theoretical work was written by Mendes, Monica;Garcia, Gustavo;Bacchus-Montabonel, Marie-Christine;Limao-Vieira, Paulo. And the article was included in International Journal of Molecular Sciences in 2019.Synthetic Route of C4H5N3O2 This article mentions the following:

Electron transfer induced decomposition mechanism of nitroimidazole and a selection of analog mols. in collisions with neutral potassium (K) atoms from 10 to 1000 eV have been thoroughly investigated. In this laboratory collision regime, the formation of neg. ions was time-of-flight mass analyzed and the fragmentation patterns and branching ratios have been obtained. The most abundant anions have been assigned to the parent mol. and the nitrogen oxide anion (NO₂^–) and the electron transfer mechanisms are comprehensively discussed. This work focuses on the anal. of all fragment anions produced and it is complementary of our recent work on selective hydrogen loss from the transient neg. ions produced in these collisions. Ab initio theor. calculations were performed for 4-nitroimidazole (4NI), 2-nitroimidazole (2NI), 1-methyl-4- (Me4NI) and 1-methyl-5-nitroimidazole (Me5NI), and imidazole (IMI) in the presence of a potassium atom and provided a strong basis for the assignment of the lowest unoccupied MOs accessed in the collision process. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Synthetic Route of 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Synthetic Route of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of imidazo[1,2-a]benzimidazole and imidazolino-[1,2-a]benzimidazole derivatives was written by Simonov, A. M.;Kochergin, P. M.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1965.Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole This article mentions the following:

Reaction of 1-alkyl-2-aminobenzimidazoles with α-halo ketones and α-halo alcs. gave the corresponding 1,3-disubstituted 2-iminobenzimidazolines, which under the action of dehydrating agents or by heating with mineral or organic acids lost H₂O and gave derivatives of [1,2-a]benzimidazole (I) or the corresponding 2,3-dihydro compounds Thus were obtained: 1-ethyl-3-phenacyl-2-iminobenzimidazoline, m. 120.5° (aqueous MeOH) [hydrobromide m. 2222.5° (decomposition, MeOH)]; 2-phenyl-9-ethylimidazo[1,2-a]benzimidazole, m. 93-3.5° (aqueous EtOH) [picrate m. 238-40° (decomposition, EtOH)]; 1-ethyl-3-(β-hydroxyethyl)-2-iminobenzimidazoline, m. 122.5-23° (C₂H₄Cl₂) [hydrobromide m. 226.5-27° (decomposition, EtOH); picrate m. 182-3° (H₂O)]; and 9-ethylimidazolino[1,2-a]benzimidazole [picrate m. 267-8° (decomposition, AcOH)]. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Application In Synthesis of 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. 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.Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem