Category: imidazoles-derivatives

A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor was written by Griffith, David A.;Edmonds, David J.;Fortin, Jean-Philippe;Kalgutkar, Amit S.;Kuzmiski, J. Brent;Loria, Paula M.;Saxena, Aditi R.;Bagley, Scott W.;Buckeridge, Clare;Curto, John M.;Derksen, David R.;Dias, Joao M.;Griffor, Matthew C.;Han, Seungil;Jackson, V. Margaret;Landis, Margaret S.;Lettiere, Daniel;Limberakis, Chris;Liu, Yuhang;Mathiowetz, Alan M.;Patel, Jayesh C.;Piotrowski, David W.;Price, David A.;Ruggeri, Roger B.;Tess, David A.. And the article was included in Journal of Medicinal Chemistry in 2022.Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

Peptide agonists of the glucagon-like peptide-1 receptor (GLP-1R) have revolutionized diabetes therapy, but their use has been limited because they require injection. Herein, we describe the discovery of the orally bioavailable, small-mol., GLP-1R agonist PF-06882961 (danuglipron). A sensitized high-throughput screen was used to identify 5-fluoropyrimidine-based GLP-1R agonists that were optimized to promote endogenous GLP-1R signaling with nanomolar potency. Incorporation of a carboxylic acid moiety provided considerable GLP-1R potency gains with improved off-target pharmacol. and reduced metabolic clearance, ultimately resulting in the identification of danuglipron. Danuglipron increased insulin levels in primates but not rodents, which was explained by receptor mutagenesis studies and a cryogenic electron microscope structure that revealed a binding pocket requiring a primate-specific tryptophan 33 residue. Oral administration of danuglipron to healthy humans produced dose-proportional increases in systemic exposure (NCT03309241). This opens an opportunity for oral small-mol. therapies that target the well-validated GLP-1R for metabolic health. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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 This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Inelastic neutron scattering study on boson peaks of imidazolium-based ionic liquids was written by Kofu, Maiko;Inamura, Yasuhiro;Moriya, Yosuke;Podlesnyak, Andrey;Ehlers, Georg;Yamamuro, Osamu. And the article was included in Journal of Molecular Liquids in 2015.Reference of 79917-89-8 This article mentions the following:

Low energy excitations of 1-alkyl-3-methylimidazolium ionic liquids (ILs) have been investigated by means of neutron spectroscopy. In the spectra of inelastic scattering, a broad excitation peak referred to as a “boson peak” appeared at 1-3 meV in all of the ILs measured. The intensity of the boson peak was enhanced at the Q positions corresponding to the diffraction peaks, reflecting the in-phase vibrational nature of the boson peak. Furthermore the boson peak energy (E_BP) was insensitive to the length of the alkyl-chain but changed depending on the radius of the anion. From the correlation among E_BP, the anion radius, and the glass transition temperature T_g, we conclude that both E_BP and T_g in ILs are predominantly governed by the inter-ionic Coulomb interaction which is less influenced by the alkyl-chain length. We also found that the E_BP is proportional to the inverse square root of the mol. weight as observed in mol. glasses. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Reference of 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Reference of 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

NAE modulators: A potential therapy for gastric carcinoma was written by Liang, Qi;Liu, Maoyu;Li, Jian;Tong, Rongsheng;Hu, Yonghe;Bai, Lan;Shi, Jianyou. And the article was included in European Journal of Medicinal Chemistry in 2022.Product Details of 145040-37-5 This article mentions the following:

Neural precursor cell expressed developmentally downregulated protein-8 (NEDD8) is a ubiquitin-like protein, which activates an important post-translational modification process: neddylation, thereby regulating the stability and degradation of various proteins related to multiple physiol. processes. And the abnormal activation of NEDD8 (overexpression or underexpression) is related to the occurrence of multiple cancers including gastric carcinoma. NEDD8 activating enzyme (NAE), a key enzyme for the activation of NEDD8, controls the initiation of the NEDD8 transfer cascade, which is an important target for anti-tumor drugs. With the disclosure of the anti-tumor mechanism, NAE modulators (inhibitors and agonists) have gradually become a research hotspot in the development of anti-tumor drugs. And the application of NAE modulators has also been further expanded, not only limited to certain hematol. tumors, its therapeutic potential in multiple solid tumors, especially gastric carcinoma, has been gradually uncovered. This paper mainly explains the structural characteristics, catalytic sites, and mechanism of NAE. And the relationships between neddylation and tumors are also elaborated from the perspective of NAE regulating the downstream pathways. In addition, the NAE modulators reported in recent years were reviewed, mainly focusing on their discovery processes, structure-activity relationships, inhibitory efficacy, pharmacol. mechanism, and clin. research. And we reasonably predict the application of NAE modulators in gastric carcinoma, according to its relationship with neddylation. We summarize the issues in NAE modulator development and discuss the possible development directions. 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. 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 Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Product Details of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds was written by Moon, Malcolm W.;Morris, Jeanette K.;Heier, Richard F.;Chidester, Connie G.;Hoffmann, William E.;Piercey, Montford F.;Althaus, John S.;VonVoigtlander, Philip F.;Evans, Dawna L.. And the article was included in Journal of Medicinal Chemistry in 1992.Name: 7-Methyl-1H-benzo[d]imidazole This article mentions the following:

The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (I), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT_1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of I; the (S)-enantiomer shows no dopaminergic activity. A series of analogs where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (II), was a selective serotonergic agonist. Various analogs of I where the dipropylamine substituent was modified were prepared Most of these showed reduced dopaminergic activity, while several were as potent as I at the serotonin 5HT_1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Name: 7-Methyl-1H-benzo[d]imidazole).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Structure-Guided Screening for Functionally Selective D₂ Dopamine Receptor Ligands from a Virtual Chemical Library was written by Maennel, Barbara;Jaiteh, Mariama;Zeifman, Alexey;Randakova, Alena;Moeller, Dorothee;Huebner, Harald;Gmeiner, Peter;Carlsson, Jens. And the article was included in ACS Chemical Biology in 2017.COA of Formula: C4H9Cl2N3 This article mentions the following:

Functionally selective ligands stabilize conformations of G protein-coupled receptors (GPCRs) that induce a preference for signaling via a subset of the intracellular pathways activated by the endogenous agonists. The possibility to fine-tune the functional activity of a receptor provides opportunities to develop drugs that selectively signal via pathways associated with a therapeutic effect and avoid those causing side effects. Animal studies have indicated that ligands displaying functional selectivity at the D₂ dopamine receptor (D₂R) could be safer and more efficacious drugs against neuropsychiatric diseases. In this work, computational design of functionally selective D₂R ligands was explored using structure-based virtual screening. Mol. docking of known functionally selective ligands to a D₂R homol. model indicated that such compounds were anchored by interactions with the orthosteric site and extended into a common secondary pocket. A tailored virtual library with close to 13 000 compounds bearing 2,3-dichlorophenylpiperazine, a privileged orthosteric scaffold, connected to diverse chem. moieties via a linker was docked to the D₂R model. Eighteen top-ranked compounds that occupied both the orthosteric and allosteric site were synthesized, leading to the discovery of 16 partial agonists. A majority of the ligands had comparable maximum effects in the G protein and 尾-arrestin recruitment assays, but a subset displayed preference for a single pathway. In particular, compound I stimulated 尾-arrestin recruitment (EC₅₀ = 320 nM, E_max = 16%) but had no detectable G protein signaling. The use of structure-based screening and virtual libraries to discover GPCR ligands with tailored functional properties will be discussed. In the experiment, the researchers used many compounds, for example, (1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7COA of Formula: C4H9Cl2N3).

(1H-Imidazol-2-yl)methanamine dihydrochloride (cas: 22600-77-7) 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.COA of Formula: C4H9Cl2N3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Influencing factors on decomposition of ammonium chloride and organic base hydrochloride was written by Bian, Siyu;Guan, Congcong;Wang, Shufang;Wang, Yanji. And the article was included in Huaxue Fanying Gongcheng Yu Gongyi in 2019.Reference of 35487-17-3 This article mentions the following:

Ammonium chloride is a byproduct of Hou鈥瞫 process for soda manufacture In order to achieve efficient use of nitrogen and chlorine, and fundamentally solve the problems of byproduct surplus and environmental pollution, several organic bases of different structures were selected to study the reaction process of decomposing ammonium chloride to release ammonia gas, and organic base hydrochloride to release hydrogen chloride. The effect of organic alkalinity, structure and solvation on the reaction was correlated. The results showed that the organic alkalinity did not show a completely pos. correlation with the decomposition of ammonium chloride and the corresponding organic base hydrochloride. Besides the alkalinity, the structure and solvation of organic base also had an important effect on the reaction. Trihexylamine and trioctylamine were suitable organic bases, which could simultaneously satisfy the decomposition process of ammonium chloride and the corresponding organic base hydrochloride. In addition, solvents also had a great influence on the reaction. The decomposition of ammonium chloride by trihexylamine and trioctylamine should be carried out in a polar alc. solution, while the decomposition of the corresponding organic base hydrochloride should be performed in a nonpolar alkane solution In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Reference of 35487-17-3).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Design and binding of a distamycin A analog to d(CGCAAGTTGGC)路d(GCCAACTTGCG): synthesis, NMR studies, and implications for the design of sequence-specific minor groove binding oligopeptides was written by Dwyer, Tammy J.;Geierstanger, Bernhard H.;Bathini, Yadagiri;Lown, J. William;Wemmer, David E.. And the article was included in Journal of the American Chemical Society in 1992.Electric Literature of C7H9N3O4 This article mentions the following:

Distamycin A analog I was prepared in which an imidazole ring is substituted for the central pyrrole ring of distamycin A. A key step in the synthesis was the coupling of acid II with amine III by EDCI to give the corresponding peptide. The latter peptide was converted into I in 3 steps. Two-dimensional NMR spectroscopy was used to characterize the complex formed between I and d(CGCAAGTTGGC)路d(GCCAACTTGCG). Titration of the AAGTT duplex with I yielded a single complex with a ligand:DNA stoichiometry of 2:1. The nuclear Overhauser effect (NOESY) experiment in D₂O was used to assign the aromatic and C1’H DNA protons and to identify intermol. ligand-DNA contacts between nonlabile protons. The NOESY experiment in H₂O was used to assign the imino and amino DNA protons and the amide protons of the ligands and to identify ligand-DNA contacts involving these labile protons. These data indicate that two ligand mols. bind simultaneously to the minor groove of the central 5′-AAGTT-3′ sequence in a head-to-tail orientation. Mol. modeling, using 35 ligand-DNA distance constraints derived from a semiquant. anal. of the NOESY data, shows that the imidazole N3 of one of the ligands forms a hydrogen bond with the C2 amino group of the guanine in the binding site. Addnl., the titration of d(CGCAAATTGGC)路d(GCCAATTTGCG) with I was performed. No specific complex was detected by NMR spectroscopy between I and the AAATT duplex. This result emphasizes the importance of the imidazole N3 atom of I in the recognition of the AAGTT binding site. In the experiment, the researchers used many compounds, for example, Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9Electric Literature of C7H9N3O4).

Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Electric Literature of C7H9N3O4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of Br蠁nsted-Lewis acidic ionic liquids and their use as catalysts in rosin dimerization was written by Wang, Jin-long;You, Xing-lin;Fang, Yun. And the article was included in Jingxi Huagong in 2014.Recommanded Product: 35487-17-3 This article mentions the following:

A Br蠁nsted acidic ionic liquid mim 路 HCl was synthesized as an intermediate by protonating N-Me imidazole with Br蠁nsled acid donor hydrochloric acid. And a group of dual acidic ionic liquid 1-hydro-3-methylimidazole chloride chloroironinates (1-蠂) [mim 路 HCl] 蠂 [FeCl₃] (where 蠂 is the mole fractions of the Lewis acid) was synthesized from the reaction of mim 路HCl and a Lewis acid donor FeCl₃. The acidity of the group was characterized and compared to each other by means of FTIR in virtue of pyridine and acetonitrile mol. probe, resp. The dual acidic ionic liquids were then employed lo catalyze rosin dimerization. A dimeric rosin acid with a softening point of 102.4 degree C was obtained using (1-蠂) [mim路HCl]蠂[FeCl₃] (蠂=0.64) as catalyst, which was 15 degree C higher than that without using catalyst. The catalytic activity became weaker after the fifth use. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Recommanded Product: 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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Recommanded Product: 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A Three-In-One Assembled Nanoparticle Containing Peptide-Radio-Sensitizer Conjugate and TLR7/8 Agonist Can Initiate the Cancer-Immunity Cycle to Trigger Antitumor Immune Response was written by Zhu, Xueqin;Wang, Xiaoxi;Li, Bingyu;Zhang, Yun;Chen, Yalan;Zhang, Wenyan;Wang, Yan;Zhai, Wenjie;Liu, Zimai;Liu, Sijia;Sun, Jiaxin;Chen, Zhenzhen;Gao, Yanfeng. And the article was included in Small in 2022.Application In Synthesis of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:

Radiotherapy (RT) has been shown to cause immunogenic cell death (ICD) of cancer cells, which promote the release of tumor-associated antigens, and trigger the cancer-immunity cycle (CIC). However, ICD induced by RT usually does not occur in hypoxic tumor cells due to their resistance to radiation. Moreover, RT also induces programmed death ligand 1 (PD-L1) upregulation on tumor cells, which has an inhibitory effect on T lymphocytes. Therefore, therapy based on CIC must selectively target the restricted steps of antitumor immunity. Herein, the authors design a versatile three-in-one assembling nanoparticle that can simultaneously execute these obstacles. The amphiphilic peptide drug conjugate NIA-D1, containing the hydrophobic radio-sensitizer 2-(2-nitroimidazol-1-yl) acetic acid (NIA), a peptide substrate of matrix metalloproteinase-2, and a hydrophilic PD-L1 antagonist DPPA-1, is constructed and co-assembled with hydrophobic Toll-like receptor (TLR) 7/8 agonist R848 to form nanoparticle NIA-D1@R848. The NIA-D1@R848 nanoparticles combined with RT can trigger the apoptosis of tumor cells and initiate the CIC. In the presence of R848, it promotes the maturation of dendritic cells, which together with protein programmed cell death protein 1 (PD-1) and its ligand PD-L1 blockade to relieve T cell suppression, and amplify the antitumor immune cycle. In conclusion, a functionalized three-in-one nanoparticle NIA-D1@R848 is successfully constructed, which can induce strong systemic antitumor immune response. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Application In Synthesis 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 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.Application In Synthesis of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effect of substituents on the electronic structure and spectral characteristics of imidazole derivatives in the ground and excited states was written by Prokop’eva, T. M.;Vysotskii, Yu. B.;Dadali, V. A.;Sokolenko, V. A.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1982.SDS of cas: 4887-83-6 This article mentions the following:

Ground- and excited-state electron d. distributions were calculated for imidazole, benzimidazole, their protonated and anionic forms, and 1-phenylimidazole by the PMO LCAO SCF method. The results of the calculations corresponded to exptl. reactivity data. The lowest singlet-singlet transition energies were also calculated for benzimidazoles, and these agreed with exptl. spectra. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6SDS of cas: 4887-83-6).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem