Tag: 100-200

《Alkylated benzimidazoles: Design, synthesis, docking, DFT analysis, ADMET property, molecular dynamics and activity against HIV and YFV》 was published in Computational Biology and Chemistry in 2020. These research results belong to Srivastava, Ritika; Gupta, Sunil K.; Naaz, Farha; Sen Gupta, Parth Sarthi; Yadav, Madhu; Singh, Vishal Kumar; Singh, Anuradha; Rana, Malay Kumar; Gupta, Satish Kumar; Schols, Dominique; Singh, Ramendra K.. Related Products of 4857-06-1 The article mentions the following:

A series of alkylated benzimidazole derivatives I [R1 = H, Br, NO2; R2 = H, Br, NO2; R3 = (CH2)2OH, (CH2)3OH] was synthesized and screened for their anti-HIV, anti-YFV, and broad-spectrum antiviral properties. The physicochem. parameters and drug-like properties of the compounds were assessed first, and then docking studies and MD simulations on HIV-RT allosteric sites were conducted to find the possible mode of their action. DFT anal. was also performed to confirm the nature of the hydrogen bonding interaction of active compounds The in silico studies indicated that the mols. behaved like possible NNRTIs. The nature – polar or non-polar and position of the substituent present at fifth, sixth, and N-1 positions of the benzimidazole moiety played an important role in determining the antiviral properties of the compounds Among the various compounds, I (R1 = R2 = Br; R3 = (CH2)2OH) showed anti-HIV activity with an appreciably low IC50 value as 0.386 x 10-5μM. Similarly, compound I (R1 = NO2; R2 = H; R3 = (CH2)3OH), showed excellent inhibitory property against the yellow fever virus (YFV) with EC50 value as 0.7824 x 10-2μM. In the experiment, the researchers used many compounds, for example, 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Related Products of 4857-06-1)

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.Related Products of 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Intermolecular, Branch-Selective, and Redox-Neutral Cp*IrIII-Catalyzed Allylic C-H Amidation》 were Knecht, Tobias; Mondal, Shobhan; Ye, Jian-Heng; Das, Mowpriya; Glorius, Frank. And the article was published in Angewandte Chemie, International Edition in 2019. SDS of cas: 530-62-1 The author mentioned the following in the article:

Herein, we report the redox-neutral, intermol., and highly branch-selective amidation of allylic C-H bonds enabled by Cp*IrIII catalysis. A variety of readily available carboxylic acids were converted into the corresponding dioxazolones and efficiently coupled with terminal and internal olefins in high yields and selectivities. Mechanistic investigations support the formation of a nucleophilic IrIII-allyl intermediate rather than the direct insertion of an Ir-nitrenoid species into the allylic C-H bond. In the experiment, the researchers used many compounds, for example, Di(1H-imidazol-1-yl)methanone(cas: 530-62-1SDS of cas: 530-62-1)

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a coupling agent in the synthesis of dipolar polyamides for nonlinear optical applications and polypeptides. It also used to make β-keto sulfones and sulfoxides, lead sequestering agents, and β-enamino acid derivatives.SDS of cas: 530-62-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2010,Garton, Neil; Bailey, Nick; Bamford, Mark; Demont, Emmanuel; Farre-Gutierrez, Irene; Hutley, Gail; Bravi, Gianpaolo; Pickering, Paula published 《Discovery of biaryl inhibitors of H+/K+ ATPase》.Bioorganic & Medicinal Chemistry Letters published the findings.Synthetic Route of C3H3BrN2 The information in the text is summarized as follows:

We report the identification of a novel biaryl template for H+/K+ ATPase inhibition. Evaluation of critical SAR features within the biaryl imidazole framework and the use of pharmacophore modeling against known imidazopyridine and azaindole templates suggested that the geometry of the mol. is key to achieving activity. Herein we present our work optimizing the potency of the mol. through modifications and substitutions to each of the ring systems. In particular sub-micromolar potency is achieved with (4b) presumably through a proposed intramol. hydrogen bond that ensures the required imidazole basic center is appropriately located. In the experiment, the researchers used many compounds, for example, 2-Bromo-1H-imidazole(cas: 16681-56-4Synthetic Route of C3H3BrN2)

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. Synthetic Route of C3H3BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2003,Australian Journal of Chemistry included an article by Indusegaram, Sutharsiny; Katsifis, Andrew G.; Ridley, Damon D.; Vonwiller, Simone C.. Formula: C10H12N2O. The article was titled 《Nitrogen versus Oxygen Group Protection in Hydroxypropylbenzimidazoles》. The information in the text is summarized as follows:

In order to convert 1’H-benzimidazol-2′-yl-propanols into aryl ethers using Mitsunobu coupling, it was necessary to protect the benzimidazole nitrogen in the starting alcs. Selective protection at nitrogen was achieved through N-benzyl derivatives, but attempts to protect the nitrogen directly through tert-butoxycarbonyl, acetyl, trityl, or tetrahydropyranyl derivatives were complicated either by selective reactions at oxygen or by the formation of bis-protected compounds Transformations of some oxygen-protected derivatives are discussed, and in particular the conversion of the acetates of 1’H-benzimidazol-2′-yl-propanols to N-tetrahydropyranyl derivatives is described. Mitsunobu coupling involving the N-benzyl and N-tetrahydropyranyl derivatives and Me 4-hydroxybenzoate were achieved, and thus afforded synthetic routes to the desired propylbenzimidazole aryl ethers. The experimental part of the paper was very detailed, including the reaction process of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Formula: C10H12N2O)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
Formula: C10H12N2O However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Product Details of 530-62-1In 2022 ,《Supramolecular self-associating amphiphiles: determination of molecular self-association properties and calculation of critical micelle concentration using a high-throughput, optical density based methodology》 was published in Organic & Biomolecular Chemistry. The article was written by Rutkauskaite, Andzelika; White, Lisa J.; Hilton, Kira L. F.; Picci, Giacomo; Croucher, Lorraine; Caltagirone, Claudia; Hiscock, Jennifer R.. The article contains the following contents:

Supramol. self-associating amphiphiles are a class of amphiphilic salt, the anionic component of which is ′frustrated′ in nature, meaning multiple hydrogen bonding modes can be accessed simultaneously. Here we derive critical micelle concentration values for four supramol. self-associating amphiphiles using the standard pendant drop approach and present a new high-throughput, optical d. measurement based methodol., to enable the estimation of critical micelle concentrations over multiple temperatures In addition, we characterize the low-level hydrogen bonded self-association events in the solid state, through single crystal X-ray diffraction, and in polar organic DMSO-d6 solutions using a combination of 1H NMR techniques. Moving into aqueous ethanol solutions (EtOH/H2O or EtOH/D2O (1 : 19 volume/volume)), we also show these amphiphilic compounds to form higher-order self-associated species through a combination of 1H NMR, dynamic light scattering and zeta potential studies. In the experimental materials used by the author, we found Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Product Details of 530-62-1)

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a coupling agent in the synthesis of dipolar polyamides for nonlinear optical applications and polypeptides. It also used to make β-keto sulfones and sulfoxides, lead sequestering agents, and β-enamino acid derivatives.Product Details of 530-62-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Category: imidazoles-derivativesIn 2017 ,《Structure-activity relationships of rosiglitazone for peroxisome proliferator-activated receptor gamma transrepression》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Toyota, Yosuke; Nomura, Sayaka; Makishima, Makoto; Hashimoto, Yuichi; Ishikawa, Minoru. The article contains the following contents:

Anti-inflammatory effects of peroxisome proliferator-activated receptor gamma (PPRAγ) ligands are thought to be largely due to PPARγ-mediated transrepression. Thus, transrepression-selective PPARγ ligands without agonistic activity or with only partial agonistic activity should exhibit anti-inflammatory properties with reduced side effects. Here, the authors investigated the structure-activity relationships (SARs) of PPARγ agonist rosiglitazone, focusing on transrepression activity. Alkenic analogs showed slightly more potent transrepression with reduced efficacy of transactivating agonistic activity. Removal of the alkyl group on the nitrogen atom improved selectivity for transrepression over transactivation. Among the synthesized compounds, I exhibited stronger transrepressional activity (IC50: 14 μM) and weaker agonistic efficacy (11%) than rosiglitazone or pioglitazone. After reading the article, we found that the author used 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Category: imidazoles-derivatives)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) is an analog of benzimidazole that has been synthesized by Langmuir adsorption isotherm. It is a white crystalline solid that can be dissolved in water and hydrochloric acid. 2-Chloro-1H-benzo[d]imidazole inhibits the growth of herpes simplex virus by acting as a competitive inhibitor for the viral enzyme thymidine kinase, which catalyzes the conversion of thymine to thymidine.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Evans, Courtney; Morimitsu, Yuto; Nishi, Rikako; Yoshida, Masahiro; Takei, Takayuki published an article in Journal of Bioscience and Bioengineering. The title of the article was 《Novel hydrophobically modified agarose cryogels fabricated using dimethyl sulfoxide》.Category: imidazoles-derivatives The author mentioned the following in the article:

Drug delivery systems (DDS) are devices able to adsorb therapeutic drugs in vitro before being either injected or surgically implanted into the body before releasing the drugs in vivo. Hydrogels are interesting for DDS researchers as they mimic soft tissue and can absorb large quantities of liquid This research reported the successful fabrication of hydrophobically modified agarose (HMA) as well as the creation of a novel approach to the formation of hydrophobically modified agarose cryogels. By activating the hydroxyl groups in agarose, hydrophobic modification could occur through the bonding of the activated hydroxyl groups and the amines in fatty aldehydes. It was found that HMA was insoluble in water, and as such a new method of cryogel creation was produced using DMSO. Further testing of HMA cryogels showed that cell adhesiveness and cytotoxicity were low. Adsorption tests showed that HMA cryogels had the ability to adsorb larger amounts of hydrophobic dye than unmodified agarose cryogels and that the release of the hydrophobic dye from HMA cryogels could be controlled. These results showed that the HMA cryogels made using this novel approach have the potential to be used as drug delivery systems. In the experiment, the researchers used many compounds, for example, Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Category: imidazoles-derivatives)

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.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Wang, Zhongjuan; Xu, Shaobin; Xia, Hongying; Liu, Yanqiu; Li, Bin; Liang, Yueqin; Li, Zhongkun published an article in Drug Development and Industrial Pharmacy. The title of the article was 《A cationic cyclodextrin derivative-lipid hybrid nanoparticles for gene delivery effectively promotes stability and transfection efficiency》.Recommanded Product: Di(1H-imidazol-1-yl)methanone The author mentioned the following in the article:

Genetic medicines hold great promise for treatment of a number of diseases; however, the development of effective gene delivery carrier is still a challenge. The commonly used gene carrier liposomes and cationic polymers have limited their clin. application due to their resp. disadvantages. Lipid-polymer hybrid nanoparticles (LHNPs) are novel drug delivery system that exhibit complementary characteristics of both polymeric nanoparticles and liposomes. In this account, we developed the α-cyclodextrin-conjugated generation-2 polyamidoamine dendrimers-lipids hybrid nanoparticles (CDG2-LHNPs) for gene delivery. The pDNA/CDG2-LHNPs was stable during 15 days of storage period both at 4 °C, 25 °C, and 37 °C, whereas the particle size of pDNA/CDG2 and pDNA/liposomes dramatically increased after storage at 4 °C for 8 h. CDG2-LHNPs showed significantly superior transfection efficiencies compared to either CDG2 or liposomes. The mechanism of high transfection efficiency of pDNA/CDG2-LHNPs was further explored using pharmacol. inhibitors chlorpromazine, filipin, and cytochalasion D. The result demonstrated that cell uptake of pDNA/CDG2-LHNPs was mediated by clathrin-mediated endocytosis (CME), caveolae-mediated endocytosis (CvME), and macropinocytosis together. pDNA/CDG2-LHNPs were more likely be taken up by cells through CvME, which avoided lysosomal degradation to a large extent. Moreover, the liposome component of pDNA/CDG2-LHNPs increased its cell uptake efficiency, and the CDG2 polymer component increased its proton buffer capacity, so the hybrid nanoparticles taken up by CME could also successfully escape from the lysosome. CDG2-LHNPs with stability and high-transfection efficiency overcome the shortcomings of liposomes and polymers applied sep., and have great potential for gene drug delivery. The experimental part of the paper was very detailed, including the reaction process of Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Recommanded Product: Di(1H-imidazol-1-yl)methanone)

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.Recommanded Product: Di(1H-imidazol-1-yl)methanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Devine, Shane M.; Challis, Matthew P.; Kigotho, Jomo K.; Siddiqui, Ghizal; De Paoli, Amanda; MacRaild, Christopher A.; Avery, Vicky M.; Creek, Darren J.; Norton, Raymond S.; Scammells, Peter J. published their research in European Journal of Medicinal Chemistry in 2021. The article was titled 《Discovery and development of 2-aminobenzimidazoles as potent antimalarials》.SDS of cas: 934-32-7 The article contains the following contents:

The design, synthesis and antimalarial activity of a series of 2-aminobenzimidazoles I [R = H, NH2, NHEt, NHBn, etc.; Ar = 2-HOC6H4, 2-NH2C6H4, benzofuran-7-yl, etc.], featuring a phenol moiety that was crucial to the pharmacophore. Two potent mols. exhibited IC50 values against P. falciparum 3D7 strain of 42 ± 4 I [R = NH2; Ar = 5-Me-2-HOC6H3] and 43 ± 2 nM [R = NH2; Ar = 5-MeO-2-HOC6H3] and high potency against strains resistant to chloroquine (Dd2), artemisinin (Cam3.IIC580Y) and PfATP4 inhibitors (SJ557733), while demonstrating no cytotoxicity against human cells (HEK293, IC50 > 50μM). The most potent mol., possessing a 4,5-di-Me substituted phenol I [R = NH2; Ar = 4,5-(MeO)2-2-HOC6H2] displayed an IC50 value of 6.4 ± 0.5 nM against P. falciparum 3D7, representing a 12-fold increase in activity from the parent mol. The 2-aminobenzimidazoles containing a N1-substituted phenol represented a new class of mols. that had high potency in vitro against P. falciparum malaria and low cytotoxicity. They possessed attractive pharmaceutical properties, including low mol. weight, high ligand efficiency, high solubility, synthetic tractability and low in vitro clearance in human liver microsomes. After reading the article, we found that the author used 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7SDS of cas: 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.SDS of cas: 934-32-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2018,Archiv der Pharmazie (Weinheim, Germany) included an article by Keeley, Aaron; Abranyi-Balogh, Peter; Hrast, Martina; Imre, Timea; Ilas, Janez; Gobec, Stanislav; Keseru, Gyoergy M.. Electric Literature of C3H3BrN2. The article was titled 《Heterocyclic electrophiles as new MurA inhibitors》. The information in the text is summarized as follows:

An electrophilic fragment library of small heterocycles was developed and characterized in the surrogate GSH-reactivity assay and aqueous stability test that revealed their potential as covalent warheads. Screening the library against MurA from Staphylococcus aureus (MurASA) and Escherichia coli (MurAEC) identified heterocyclic fragments with significant inhibitory potency. The validated heterocyclic warhead library might be useful for developing targeted covalent inhibitors for other targets of interest with a new design strategy incorporating heterocyclic electrophiles as warheads. In addition to this study using 2-Bromo-1H-imidazole, there are many other studies that have used 2-Bromo-1H-imidazole(cas: 16681-56-4Electric Literature of C3H3BrN2) was used in this study.

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. Electric Literature of C3H3BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem