Month: October 2022

Venable, Jennifer D.; Cai, Hui; Chai, Wenying; Dvorak, Curt A.; Grice, Cheryl A.; Jablonowski, Jill A.; Shah, Chandra R.; Kwok, Annette K.; Ly, Kiev S.; Pio, Barbara; Wei, Jianmei; Desai, Pragnya J.; Jiang, Wen; Nguyen, Steven; Ling, Ping; Wilson, Sandy J.; Dunford, Paul J.; Thurmond, Robin L.; Lovenberg, Timothy W.; Karlsson, Lars; Carruthers, Nicholas I.; Edwards, James P. published their research in Journal of Medicinal Chemistry on December 29 ,2005. The article was titled 《Preparation and Biological Evaluation of Indole, Benzimidazole, and Thienopyrrole Piperazine Carboxamides: Potent Human Histamine H4 Antagonists》.Product Details of 3584-66-5 The article contains the following contents:

Three series of H4 receptor ligands, derived from indoly-2-yl-(4-methyl-piperazin-1-yl)methanones, have been synthesized and their structure-activity relationships evaluated for activity at the H4 receptor in competitive binding and functional assays. In all cases, substitution of small lipophilic groups in the 4 and 5-positions led to increased activity in a [3H]histamine radiolabeled ligand competitive binding assay. In vitro metabolism and initial pharmacokinetic studies were performed on selected compounds leading to the identification of carboxamides I [X = CH, N] as potent H4 antagonists with the potential for further development. In addition, I demonstrated efficacy in in vitro mast cell and eosinophil chemotaxis assays. After reading the article, we found that the author used 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole(cas: 3584-66-5Product Details of 3584-66-5)

5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole(cas: 3584-66-5) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
However, the application of imidazoles is not limited to the field of peptides and peptidomimetics. Product Details of 3584-66-5

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

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

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 2018,Milton, Morgan E.; Minrovic, Bradley M.; Harris, Danni L.; Kang, Brian; Jung, David; Lewis, Caleb P.; Thompson, Richele J.; Melander, Roberta J.; Zeng, Daina; Melander, Christian; Cavanagh, John published 《Re-sensitizing multidrug resistant bacteria to antibiotics by targeting bacterial response regulators: characterization and comparison of interactions between 2-aminoimidazoles and the response regulators BfmR from Acinetobacter baumannii and QseB from Francisella spp.》.Frontiers in Molecular Biosciences published the findings.Related Products of 7720-39-0 The information in the text is summarized as follows:

2-Aminoimidazole (2-AI) compounds inhibit the formation of bacterial biofilms, disperse preformed biofilms, and re-sensitize multidrug resistant bacteria to antibiotics. 2-Als have previously been shown to interact with bacterial response regulators, but the mechanism of interaction is still unknown. Response regulators are one part of two-component systems (TCS). TCSs allow cells to respond to changes in their environment, and are used to trigger quorum sensing, virulence factors, and antibiotic resistance. Drugs that target the TCS signaling process can inhibit pathogenic behavior, making this a potent new therapeutic approach that has not yet been fully exploited. We previously laid the groundwork for the interaction of the Acinetobacter baumannii response regulator BfmR with an early 2-AI derivative Here, we further investigate the response regulator/2-AI interaction and look at a wider library of 2-AI compounds By combining mol. modeling with biochem. and cellular studies, we expand on a potential mechanism for interaction between response regulators and 2-AIs. We also establish that Francisella tularensis/novicida, encoding for only three known response regulators, can be a model system to study the interaction between 2-AIs and response regulators. We show that knowledge gained from studying Francisella can be applied to the more complex A. baumannii system, which contains over 50 response regulators. Understanding the impact of 2-AIs on response regulators and their mechanism of interaction will lead to the development of more potent compounds that will serve as adjuvant therapies to broad-range antibiotics. In the experimental materials used by the author, we found 1H-Imidazol-2-amine(cas: 7720-39-0Related Products of 7720-39-0)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Related Products of 7720-39-0

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2018,Trang, Tran Thi Thu; Dieltjens, Lise; Hooyberghs, Geert; Waldrant, Kai; Ermolat’ev, Denis S.; Van der Eycken, Erik V.; Steenackers, Hans P. L. published 《Enhancing the anti-biofilm activity of 5-aryl-2-aminoimidazoles through nature inspired dimerisation》.Bioorganic & Medicinal Chemistry published the findings.Computed Properties of C3H5N3 The information in the text is summarized as follows:

The increased tolerance of biofilms against disinfectants and antibiotics has stimulated research into new methods of biofilm prevention and eradication. In our previous work, we have identified the 5-aryl-2-aminoimidazole core as a scaffold that demonstrates preventive activity against biofilm formation of a broad range of bacterial and fungal species. Inspired by the dimeric nature of natural 2-aminoimidazoles of the oroidin family, we investigated the potential of dimers of our decorated 5-aryl-2-aminoimidazoles as biofilm inhibitors. A synthetic approach towards 2-aminoimidazole dimers linked by an alkyl chain was developed and a total of 48 dimers were synthesized. The linkers were introduced at two different positions, the N1-position or the N2-position, and the linker length and the substitution of the 5-Ph ring (H, F, Cl, Br) were varied. Although, no clear correlation between linker length and biofilm inhibition was observed, a strong increase in anti-biofilm activity for almost all N1,N1′-linked dimers was obtained, compared to the resp. monomers against Salmonella Typhimurium, Escherichia coli and Staphylococcus aureus. The N2,N2′-linked dimers, having a H- or F-substitution, were also found to show a strong increase in anti-biofilm activity compared to the resp. monomers against these three bacterial species and against Pseudomonas aeruginosa. In addition, the obtained growth measurements suggest a broad concentration range with specific biofilm inhibition and no effect on the planktonic growth against Salmonella Typhimurium and Pseudomonas aeruginosa. In the experimental materials used by the author, we found 1H-Imidazol-2-amine(cas: 7720-39-0Computed Properties of C3H5N3)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Computed Properties of C3H5N3

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

The author of 《Synthesis of novel galeterone derivatives and evaluation of their in vitro activity against prostate cancer cell lines》 were Jorda, Radek; Reznickova, Eva; Kielczewska, Urszula; Maj, Jadwiga; Morzycki, Jacek W.; Siergiejczyk, Leszek; Bazgier, Vaclav; Berka, Karel; Rarova, Lucie; Wojtkielewicz, Agnieszka. And the article was published in European Journal of Medicinal Chemistry in 2019. HPLC of Formula: 7720-39-0 The author mentioned the following in the article:

Prostate cancer is one of the main causes of male cancer-related deaths worldwide and the suppression of androgen receptor signalling is established as an effective strategy for the treatment. A series of galeterone analogs including several steroid-fused azacycles, as well as 17-(benzimidazol-1-ylimino), 16α-(benzimidazol-2-ylamino), and 16α-(benzothiazol-2-ylamino) steroid derivatives, were synthesized and tested against prostate cancer cell lines. Candidate compound I was shown to reduce AR-regulated transcription in a dose-dependent manner in nanomolar ranges and suppress expression of AR-regulated proteins Nkx3.1 and PSA in 22Rv1-ARE14 and VCaP cancer cell lines. Flexible docking study revealed similar position of I within AR binding site in comparison of galeterone even with stronger binding energy.1H-Imidazol-2-amine(cas: 7720-39-0HPLC of Formula: 7720-39-0) was used in this study.

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.HPLC of Formula: 7720-39-0

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

The author of 《Molecular Mobility in a Set of Imidazolium-Based Ionic Liquids [bmim]+A- by the NMR-Relaxation Method》 were Bystrov, Sergei S.; Matveev, Vladimir V.; Chernyshev, Yurii S.; Balevicius, Vytautas; Chizhik, Vladimir I.. And the article was published in Journal of Physical Chemistry B in 2019. Application In Synthesis of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate The author mentioned the following in the article:

The detailed investigation of the local mobility in a set of dried imidazolium-based ionic liquids (1-butyl-3-methylimidazolium) in a wide temperature range and varying anions (BF4-, I-, Cl-, Br-, NO3-, TfO-) is presented. The measurements of temperature dependencies of the spin-lattice relaxation times of 1H and 13C nuclei are motivated by the need to obtain a fundamental characterization of mol. mobility of the substances under study, namely, to estimate the correlation times, τc, for the motion of individual mol. groups. In particular, it follows from obtained results that the mobility of the hydrocarbon “”tail”” is higher (smaller τc) than that of the imidazole ring, and this expected tendency is quantified. The effect of the influence of an anion type on the cation mobility is also analyzed. In the part of experimental materials, we found many familiar compounds, such as 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6Application In Synthesis of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. Actually, lonic liquids as innovative fluids have received wide attention only during the past two decades. The number of SCI papers published on lonic liquids has exponentially increased from a few in 1996 to >5000 in 2016, exceeding the annual growth rates of other popular scientific areas. Application In Synthesis of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem