Tag: 100-200

Electric Literature of C8H8N2OOn June 1, 2020, Sekioka, Ryuichi; Honda, Shugo; Akashiba, Hiroki; Yarimizu, Junko; Mitani, Yasuyuki; Yamasaki, Shingo published an article in Bioorganic & Medicinal Chemistry. The article was 《Optimization and biological evaluation of imidazopyridine derivatives as a novel scaffold for γ-secretase modulators with oral efficacy against cognitive deficits in Alzheimer′s disease model mice》. The article mentions the following:

Gamma-secretase modulators (GSMs) selectively lower amyloid-β42 (Aβ42) and are therefore potential disease-modifying drugs for Alzheimer′s disease (AD). Here, we report the discovery of imidazopyridine derivatives as GSMs with oral activity on not only Aβ42 levels but also cognitive function. Structural optimization of the biphenyl group and pyridine-2-amide moiety of compound 1a greatly improved GSM activity and rat microsomal stability, resp. 5-{8-[(3,4′-Difluoro[1,1′-biphenyl]-4-yl)methoxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-N-methylpyridine-2-carboxamide (1o)(I) showed high in vitro potency and brain exposure, induced a robust reduction in brain Aβ42 levels, and exhibited undetectable inhibition of cytochrome P 450 enzymes. Moreover, compound 1o showed excellent efficacy against cognitive deficits in AD model mice. These findings suggest that compound 1o is a promising candidate for AD therapeutics. The results came from multiple reactions, including the reaction of 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Electric Literature of C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
Electric Literature of C8H8N2O However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《ZIF-8 Membrane Separation Performance Tuning by Vapor Phase Ligand Treatment》 was written by Eum, Kiwon; Hayashi, Mikio; De Mello, Matheus Dorneles; Xue, Feng; Kwon, Hyuk Taek; Tsapatsis, Michael. HPLC of Formula: 934-32-7This research focused onZIF membrane separation vapor phase ligand treatment; ZIF-8; ligand-induced permselectivity; membranes; metal-organic frameworks; vapor phase. The article conveys some information:

Vapor phase ligand treatment (VPLT) of 2-aminobenzimidazole (2abIm) for 2-methylimidazole (2mIm) in ZIF-8 membranes prepared by two different methods (LIPS: ligand induced permselectivation and RTD: rapid thermal deposition) results in a notable shift of the mol. level cut-off to smaller mols. establishing selectivity improvements from ca. 1.8 to 5 for O2/N2; 2.2 to 32 for CO2/CH4; 2.4 to 24 for CO2/N2; 4.8 to 140 for H2/CH4 and 5.2 to 126 for H2/N2. Stable (based on a one-week test) oxygen-selective air separation performance at ambient temperature, 7 bar(a) feed, and 1 bar(a) sweep-free permeate with a mixture separation factor of 4.5 and oxygen flux of 2.6×10-3 mol m-2 s-1 is established. LIPS and RTD membranes exhibit fast and gradual evolution upon a 2abIm-VPLT, resp., reflecting differences in their thickness and microstructure. Functional reversibility is demonstrated by showing that the original permeation properties of the VPLT-LIPS membranes can be recovered upon 2mIm-VPLT. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7HPLC of Formula: 934-32-7)

1H-Benzo[d]imidazol-2-amine(cas: 934-32-7) can be used in the hydrolysis of a choline carbonate. It was also used in the synthesis of imidazo[1,2-a]benzimidazoles.HPLC of Formula: 934-32-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Antiulcer agents. 2. Gastric antisecretory, cytoprotective, and metabolic properties of substituted imidazo[1,2-a]pyridines and analogs》 was published in Journal of Medicinal Chemistry in 1987. These research results belong to Kaminski, James J.; Hilbert, James M.; Pramanik, B. N.; Solomon, Daniel M.; Conn, David J.; Rizvi, Razia K.; Elliott, Arthur J.; Guzik, Henry; Lovey, Raymond G.. Related Products of 79707-11-2 The article mentions the following:

In search of a successor to the imidazol[1,2-a]pyridine I (X = CH, R = OCH2Ph, R1 = Me, R2 = CH2CN) (II) (Sch 28080), a compound that exhibits gastric antisecretory and cytoprotective properties, a series of imidazopyridines, e.g., I (X = CH; R = OCH2Ph; R1 = Me, NH2; R2 = Me, CH2CN, NH2) and of imidazopyrazines, e.g., I (X = N, R = OCH2Ph, R1 = Me, R2 = NH2) (III) were prepared In three of these potential successors of II, an amino group functions as a surrogate for the 3-cyanomethyl substituent of the prototype. In addition to an evaluation of the structure-activity relationships of a series of analogs of II, preliminary studies of the pharmacodynamics and metabolism of II were performed with the aid of cyano carbon labeled versions of the drug. II is well-absorbed and extensively metabolized; the major metabolite of II is the thiocyanate anion. A similar study performed on I (X = CH, R = OCH2Ph, R1 = Me, R2 = NH2) (IV), labeled at the 3-position with carbon-13 or carbon-14, revealed that IV, which has an antisecretory/cytoprotective profile comparable to that of II, is also metabolized to thiocyanate anion, although this must occur via a different mechanism. The potential sites of protonation of the pharmacol. similar IV and the structurally related imidazo[1,2-a]pyrazine III is discussed. Predictions based on charge d. and protonation product stabilities are presented. That N1 is the site of protonation in these analogs has been definitively demonstrated by x-ray crystal structure anal., which also unequivocally established the assigned imidazopyridine and imidazo[1,2-a]pyrazine ring structures.2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Related Products of 79707-11-2) was used in this study.

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Related Products of 79707-11-2 Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins》 were Lei, Honghui; Rovis, Tomislav. And the article was published in Journal of the American Chemical Society in 2019. Formula: C7H6N4O The author mentioned the following in the article:

An efficient method for intermol. branch-selective allylic C-H amidation has been accomplished via Ir(III) catalysis. The reaction proceeds through initial allylic C-H activation, supported by the isolation and crystallog. characterization of an allyl-Ir(III) intermediate, followed by a subsequent oxidative amidation with readily available dioxazolones as nitrenoid precursors [e.g., 1-decene + dioxazolone I → amide II (73%, > 20:1 rr)]. A diverse range of amides are successfully installed at the branched position of terminal alkenes in good yields and regioselectivities. Importantly, the reaction allows the use of amide-derived nitrenoid precursors avoiding problematic Curtius-type rearrangements. The experimental part of the paper was very detailed, including the reaction process of Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Formula: C7H6N4O)

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a peptide coupling reagent,it is used in the synthesis of peptides. Reacts readily with carboxylic acids to form acyl imidazoles; subsequent reaction with amines to form amides goes smoothly.Formula: C7H6N4O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Journal of Molecular Structure included an article by Narendra babu, Kayathi; Nagarjuna, Ummadi; Reddy, Guda Dinneswara; Padmaja, Adivireddy; Padmavathi, Venkatapuram. Category: imidazoles-derivatives. The article was titled 《Synthesis and antimicrobial activity of benzazolyl azolyl urea derivatives》. The information in the text is summarized as follows:

A new class of benzazolyl azolyl urea derivatives were prepared by the reaction of Me benzazoyl carbamates with azolyl amines in the presence of mild base potassium tert-butoxide. The synthesized titled compounds were evaluated for antibacterial and antifungal actvities and the presence of electron withdrawing substituents on the aromatic ring enhanced the activity. Nitro substituted benzothiazolyl thiazolyl urea, benzothiazolyl imidazolyl urea and benzimidazolyl thiazolyl urea exhibited potential antibacterial activity against Bacillus subtilis. The compound benzothiazolyl imidazolyl urea and nitro substituted benzimidazolyl imidazolyl urea showed potential antifungal activity against Aspergillus niger. The results came from multiple reactions, including the reaction of 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7Category: imidazoles-derivatives)

1H-Benzo[d]imidazol-2-amine(cas: 934-32-7) can be used in the hydrolysis of a choline carbonate. It was also used in the synthesis of imidazo[1,2-a]benzimidazoles.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2018,Barresi, Elisabetta; Giacomelli, Chiara; Daniele, Simona; Tonazzini, Ilaria; Robello, Marco; Salerno, Silvia; Piano, Ilaria; Cosimelli, Barbara; Greco, Giovanni; Da Settimo, Federico; Martini, Claudia; Trincavelli, Maria Letizia; Taliani, Sabrina published 《Novel fluorescent triazinobenzimidazole derivatives as probes for labeling human A1 and A2B adenosine receptor subtypes》.Bioorganic & Medicinal Chemistry published the findings.Quality Control of 2-Chloro-1H-benzo[d]imidazole The information in the text is summarized as follows:

The expression levels and the subcellular localization of adenosine receptors (ARs) are affected in several pathol. conditions as a consequence of changes in adenosine release and metabolism In this respect, labeled probes able to monitor the AR expression could be a useful tool to investigate different pathol. conditions. Herein, novel ligands for ARs, bearing the fluorescent 7-nitrobenzofurazan (NBD) group linked to the N1 (1,2) or N10 (3,4) nitrogen of a triazinobenzimidazole scaffold, were synthesized. The compounds were biol. evaluated as fluorescent probes for labeling A1 and A2B AR subtypes in bone marrow-derived mesenchymal stem cells (BM-MSCs) that express both receptor subtypes. The binding affinity of the synthesized compounds towards the different AR subtypes was determined The probe 3 revealed a higher affinity to A1 and A2B ARs, showing interesting spectroscopic properties, and it was selected as the most suitable candidate to label both AR subtypes in undifferentiated MSCs. Fluorescence confocal microscopy showed that compound 3 significantly labeled ARs on cell membranes and the fluorescence signal was decreased by the cell pre-incubation with the A1 AR and A2B AR selective agonists, R-PIA and BAY 60-6583, resp., thus confirming the specificity of the obtained signal. In conclusion, compound 3 could represent a useful tool to investigate the expression pattern of both A1 and A2B ARs in different pathol. and physiol. processes. Furthermore, these results provide an important basis for the design of new and more selective derivatives able to monitor the expression and localization of each different ARs in several tissues and living cells. In addition to this study using 2-Chloro-1H-benzo[d]imidazole, there are many other studies that have used 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Quality Control of 2-Chloro-1H-benzo[d]imidazole) was used in this study.

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.Quality Control of 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2015,Kancharla, Papireddy; Kelly, Jane Xu; Reynolds, Kevin A. published 《Synthesis and Structure-Activity Relationships of Tambjamines and B-Ring Functionalized Prodiginines as Potent Antimalarials》.Journal of Medicinal Chemistry published the findings.Quality Control of 2-Bromo-1H-imidazole The information in the text is summarized as follows:

Synthesis and antimalarial activity of 94 novel bipyrrole tambjamines (TAs) and a library of B-ring functionalized tripyrrole prodiginines (PGs) against a panel of Plasmodium falciparum strains are described. The activity and structure-activity relationships demonstrate that the ring-C of PGs can be replaced by an alkylamine, providing for TAs with retained/enhanced potency. Furthermore, ring-B of PGs/TAs can be substituted with short alkyl substitutions at either 4-position (replacement of OMe) or 3- and 4-positions without impacting potency. Eight representative TAs and two PGs have been evaluated for antimalarial activity against multidrug-resistant P. yoelii in mice in the dose range of 5-100 mg/kg × 4 days by oral administration. The KAR425 TA (I) offered greater efficacy than previously observed for any PG, providing 100% protection to malaria-infected mice until day 28 at doses of 25 and 50 mg/kg × 4 days, and was also curative in this model in a single oral dose (80 mg/kg). This study presents the first account of antimalarial activity in tambjamines. In the part of experimental materials, we found many familiar compounds, such as 2-Bromo-1H-imidazole(cas: 16681-56-4Quality Control of 2-Bromo-1H-imidazole)

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. Quality Control of 2-Bromo-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Category: imidazoles-derivativesOn September 30, 1981 ,《The reaction of imidazolidine-2-thione with carbon disulfide》 was published in Journal of the Chemical Society. The article was written by Yokoyama, Masataka; Motozawa, Kosei; Kawamura, Eiichi; Imamoto, Tsuneo. The article contains the following contents:

The reaction of imidazolidine-2-thione (I) with CS2 in the presence of strong bases is reported. E. g., in the presence of NaH (THF/HMPA/DMSO) 64% bis(thioamide) II and 16% tetrahydrodiimidazothiadiazinethione III were formed, whereas reaction of I with CS2 using BuLi, followed by methylation gave 79% carbodithiolate IV. In the experiment, the researchers used many compounds, for example, Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2Category: imidazoles-derivatives)

Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. Category: imidazoles-derivatives In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Product Details of 16681-56-4In 2006 ,《Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH》 appeared in Organic & Biomolecular Chemistry. The author of the article were Clyne, Mairead A.; Aldabbagh, Fawaz. The article conveys some information:

Six-membered photochem. cyclizations of 2-iodo-N-(2-arylethyl)imidazoles proceeded regioselectively in higher yields than the equivalent tin hydride-mediated reactions. E.g., photochem. cyclizations of 2-iodo-N-(2-arylethyl)imidazole I gave 70% 5,6-dihydroimidazo[2,1-a]isoquinoline II. The decrease in yield of cyclization products, 5,6-dihydroimidazo[2,1-a]isoquinolines containing strongly deactivating substituents on the aryl ring confirmed the electrophilic nature of the σ-imidazol-2-yl radicals. The seven-membered cyclization was only successful under photochem. conditions, as radical reduction occurred with tin hydride. Nitration of 5,6-dihydroimidazo[2,1-a]isoquinolines with nitric/sulfuric acid occurred at the 2- and 8-positions. In the experiment, the researchers used many compounds, for example, 2-Bromo-1H-imidazole(cas: 16681-56-4Product Details of 16681-56-4)

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. Product Details of 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Pharmacophore modelling of 2-chlorobenzimidazole and its specific docking to the active site c-Met Kinase: A search for potent c-Met Kinase inhibitor》 was published in Pharmaceutical and Chemical Journal in 2020. These research results belong to Otuokere, I. E.; Igwe, K. K.; Amaku, J. F.; Ikpeazu, O. V.. SDS of cas: 4857-06-1 The article mentions the following:

In this paper, we demonstrate how pharmacophore modeling was used to design the analogs of 2-chlorobenzimidazole and the application of mol. docking studies in the evaluation of the ligand affinity for the target. The lead mol. (1-benzyl-2-chloro-1H-benzimidazole) had the highest docking score of -8.0 kcal/mol and was observed to interact with 17 amino acids within the pocket of c-Met Kinase (ALA159, VAL39, TYR32, MET144, ASN142, ARG141, ALA154, ASP155, ALA49, LYS51, LEU90, TYR92, MET93, GLY32, ILE, ASP97 and GLY96). Meanwhile, the ADME characteristics of 1-benzyl-2-chloro-1H-benzimidazole showed approving properties of the lead mol. Hence, we recommend 1-benzyl-2-chloro-1H-benzimidazoleas promising candidates with high potential to inhibit c-Met Kinase.2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1SDS of cas: 4857-06-1) was used in this study.

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.SDS of cas: 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem