Category: imidazoles-derivatives

2,4-Diamino-8-quinazoline carboxamides as novel, potent inhibitors of the NAD hydrolyzing enzyme CD38: Exploration of the 2-position structure-activity relationships was written by Deaton, David N.;Haffner, Curt D.;Henke, Brad R.;Jeune, Michael R.;Shearer, Barry G.;Stewart, Eugene L.;Stuart, J. Darren;Ulrich, John C.. And the article was included in Bioorganic & Medicinal Chemistry in 2018.SDS of cas: 22600-77-7 This article mentions the following:

Starting from 4-amino-8-quinoline carboxamide lead 1a and scaffold hopping to the chem. more tractable quinazoline, a systematic exploration of the 2-substituents of the quinazoline ring, utilizing structure activity relationships and conformational constraint, resulted in the identification of 39 novel CD38 inhibitors. Eight of these analogs were 10-100-fold more potent human CD38 inhibitors, including the single digit nanomolar inhibitor 1am (2-(3′-Amino-1’H-spiro[cyclopropane-1,6′-pyrrolo[3,4-c]pyrazol]-5(4H)-yl)-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carboxamide). Several of these mols. also exhibited improved therapeutic indexes relative to hERG activity. A representative analog 1r ((R)-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)-2-(6-methylpyrrolo[3,4-c]pyrazol-5(1H,4H,6H)-yl)quinazoline-8-carboxamide) exhibited suitable pharmacokinetic parameters for in vivo animal studies, including moderate clearance and good oral bioavailability. These inhibitor compounds will aid in the exploration of the enzymic functions of CD38, as well as furthering the study of the therapeutic implications of NAD enhancement in metabolic disease models. In the experiment, the researchers used many compounds, for example, (1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7SDS of cas: 22600-77-7).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis, characterization and anticancer activity of palladium allyl complexes bearing benzimidazole-based N-heterocyclic carbene (NHC) ligands was written by Scattolin, Thomas;Piccin, Andrea;Mauceri, Matteo;Rizzolio, Flavio;Demitri, Nicola;Canzonieri, Vincenzo;Visentin, Fabiano. And the article was included in Polyhedron in 2021.Name: 1-Methylbenzimidazole This article mentions the following:

The synthesis of twelve new palladium allyl complexes bearing benzimidazole-based NHC (5, NHC = N-heterocyclic carbene) ligands, [(R-MeBzIm)Pd(η³-CH₂CH:CH₂)(L)][ClO₄] (MeBzIm = 1-methylbenzimidazole, R = 3-Me, 3-Ph, 3-ⁱPr, 3-CH₂Py; L = PPh₃, PTA) and [(R¹-BzImCH₂BzIm-R¹)Pd(η³-CH₂CH:CH₂)][ClO₄] [BzImCH₂BzIm = 1,1′-methylenebis(benzimidazole), R¹ = 3-Me, 3-(1-adamantyl)], is reported. All the complexes were characterized by NMR and elemental anal. and, in the case of complex 5c (R = 3-Ph), it was possible to confirm the connectivity by single crystal X-ray diffraction. The cationic palladium allyl complexes were tested toward 5 different cancer lines, with IC₅₀ values generally lower than cisplatin and similar antiproliferative activity in the two ovarian cancer cell lines (A2780 and A2780cis), suggesting a different mechanism of action from classical platinum-based anticancer drugs. Compounds equipped with a pyridine arm or with the NHC/PTA combination (PTA = 1,3,5-triaza-7-phosphaadamantane) showed a lower cytotoxicity on normal cells with respect to cancer ones. By comparing the IC₅₀ values of mixed NHC/PTA complexes reported in this work and their trifluoromethyl congeners recently published by our group, it appears evident that they have very similar antiproliferative activity against cancer cells but the absence of the CF₃ group significantly decreases the selectivity toward them. 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. 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.Name: 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Cutaneous irritation in the topical application of 30 antineoplastic agents to New Zealand white rabbits was written by Murphy, James C.;Watson, E. S.;Wirth, P. W.;Skierkowski, Paul;Folk, R. M.;Peck, Gary. And the article was included in Toxicology in 1979.Name: 1H-Imidazole-4-carboxamide This article mentions the following:

Of 30 antineoplastic agents studied for their primary irritation potential in rabbits, 9 showed some potential for irritation. Five of these 9 agents produced a significant dermal irritation. None of the irritation observed was considered to be irreversible skin damage. The study further showed a strong correlation between irritation observed by the Draize method and acute inflammation evaluated histopathol. There was a tendency toward increased epidermal thickness of irritated skin sites. None of the agents produced gross or microscopically visible lesions in the internal organs observed In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Name: 1H-Imidazole-4-carboxamide).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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.Name: 1H-Imidazole-4-carboxamide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Evaluation of gender difference in pharmacokinetics of Candesartan cilexetil in the fasted state by RP-HPLC: A single dose comparative study was written by Nawaz, Hafiz Awais;Masood, Muhammad Irfan;Abbas, Matecn;Usman, Muhammad;Abdul, Muqeet Khan;Rasheed, Huma;Riffat, Sualeha. And the article was included in Pakistan Journal of Pharmaceutical Sciences in 2019.Application In Synthesis of 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:

To compare the pharmacokinetics of candesartan cilexetil in healthy male and female volunteers in order to identify possible influence of gender and to improve therapeutic outcomes, an HPLC method for the quantification of candesartan cilexetil was developed and validated. Total of 16 volunteers (8 male and 8 female) were registered. Candesartan cilexetil 16 mg was administered orally to all the volunteers and blood samples were collected at different time intervals between 0-72 h. Plasma was separated and analyzed by HPLC method. Pharmacokinetic parameters were calculated by using APO software MW/PHARM version 3.02 and compared in male and female volunteers. The developed HPLC method fulfils the criteria for linearity, accuracy and precision described in EMA guideline. The values for absorption rate constant (Ka), maximum plasma concentration (Cmax), volume of distribution (Vd) and Clearance (CL) were similar in male and female volunteers. No influence of gender was observed on overall pharmaco kinetics of candesartan cilexetil. Therefore, no need for dose optimization while administering candesartan cilexetil in male and female patients was found based on the results of this study. 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 In Synthesis of 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. 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 Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Application In Synthesis of 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

Asymmetric synthesis of cyclic β-amino carbonyl derivatives by a formal [3+2] photocycloaddition was written by Mollari, Leonardo;Valle-Amores, Miguel A.;Martinez-Gualda, Ana M.;Marzo, Leyre;Fraile, Alberto;Aleman, Jose. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Formula: C6H8N2O This article mentions the following:

A visible-light mediated strategy unlocking a family of cyclic β-amino carbonyl derivatives I (R = Me, cyclohexyl, 4-bromophenyl, etc.; R¹ = Ph, naphthalen-2-yl, 4-chlorophenyl, etc.; R² = H, Ts) bearing three contiguous stereogenic centers was introduced. The overall reactivity relies on the performance of the substrate-catalyst complex to assist both the enantiocontrol and the photoredox tasks. This transformation led to an enantioselective [3+2] photocycloaddition between coordinated α,β-unsaturated acyl imidazoles II and cyclopropylamine derivatives III. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Formula: C6H8N2O).

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.Formula: C6H8N2O

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

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

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

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

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