Tag: 100-200

《Discovery of Novel Small Molecule Orally Bioavailable C-X-C Chemokine Receptor 4 Antagonists That Are Potent Inhibitors of T-Tropic (X4) HIV-1 Replication》 was written by Skerlj, Renato T.; Bridger, Gary J.; Kaller, Al; McEachern, Ernest J.; Crawford, Jason B.; Zhou, Yuanxi; Atsma, Bem; Langille, Jonathon; Nan, Susan; Veale, Duane; Wilson, Trevor; Harwig, Curtis; Hatse, Sigrid; Princen, Katrien; De Clercq, Erik; Schols, Dominique. Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol And the article was included in Journal of Medicinal Chemistry on April 22 ,2010. The article conveys some information:

The redesign of azamacrocyclic CXCR4 chemokine receptor antagonists resulted in the discovery of novel, small mol., orally bioavailable compounds that retained T-tropic (CXCR4 using, X4) anti-HIV-1 activity. A structure-activity relationship (SAR) was determined on the basis of the inhibition of replication of X4 HIV-1 NL4.3 in MT-4 cells. As a result of lead optimization, we identified (S)-N’-((1H-benzo[d]imidazol-2-yl)methyl)-N’-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine (AMD070) 2 as a potent and selective antagonist of CXCR4 with an IC50 value of 13 nM in a CXCR4 125I-SDF inhibition binding assay. Compound 2 inhibited the replication of T-tropic HIV-1 (NL4.3 strain) in MT-4 cells and PBMCs with an IC50 of 2 and 26 nM, resp., while remaining noncytotoxic to cells at concentrations exceeding 23 μM. The pharmacokinetics of 2 was evaluated in rat and dog, and good oral bioavailability was observed in both species. This compound represents the first small mol. orally bioavailable CXCR4 antagonist that was developed for the treatment of HIV-1 infection. The experimental process involved the reaction of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol 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

Related Products of 4857-06-1In 2019 ,《High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides》 was published in Journal of Sulfur Chemistry. The article was written by Sohrabnezhad, Samira; Bahrami, Kiumars; Hakimpoor, Farahman. The article contains the following contents:

A new method for oxidative chlorination of thiols RSH [R = CH3(CH2)7, 2-naphthyl, cyclohexyl, ClSO2(CH2)3, etc.] to sulfonyl chlorides RSO2Cl and sulfonamides RSO2N(R1)R2 [R1 = H, C6H5, CH3CH2; R2 = cyclohexyl, 1-naphthyl, CH3CH2, etc.; R1R2 = -CH2(CH2)3CH2-] using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method. 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: 4857-06-1Related Products of 4857-06-1) was used in this study.

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.Related Products of 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application In Synthesis of Di(1H-imidazol-1-yl)methanoneIn 2022 ,《Quinolines and Oxazino-quinoline Derivatives as Small Molecule GLI1 Inhibitors Identified by Virtual Screening》 appeared in ACS Medicinal Chemistry Letters. The author of the article were Manetti, Fabrizio; Maresca, Luisa; Crivaro, Enrica; Pepe, Sara; Cini, Elena; Singh, Snigdha; Governa, Paolo; Maramai, Samuele; Giannini, Giuseppe; Stecca, Barbara; Petricci, Elena. The article conveys some information:

A virtual screening approach based on a five-feature pharmacophoric model for neg. modulators of GLI1 was applied to databases of com. available compounds The resulting quinoline derivatives showed significant ability to reduce the GLI1 protein level and were characterized by submicromolar antiproliferative activity toward human melanoma A375 and medulloblastoma DAOY cell lines. Decoration of the quinoline ring and chem. rigidification to an oxazino-quinoline scaffold allowed us to deduce SAR considerations for future ligand optimization.Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Application In Synthesis of Di(1H-imidazol-1-yl)methanone) was used in this study.

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.Application In Synthesis of Di(1H-imidazol-1-yl)methanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,McCoy, Michael A.; Spicer, Dominique; Wells, Neil; Hoogewijs, Kurt; Fiedler, Marc; Baud, Matthias G. J. published an article in Journal of Medicinal Chemistry. The title of the article was 《Biophysical Survey of Small-Molecule β-Catenin Inhibitors: A Cautionary Tale》.HPLC of Formula: 4857-06-1 The author mentioned the following in the article:

The canonical Wingless-related integration site signaling pathway plays a critical role in human physiol., and its dysregulation can lead to an array of diseases. β-Catenin is a multifunctional protein within this pathway and an attractive yet challenging therapeutic target, most notably in oncol. This has stimulated the search for potent small-mol. inhibitors binding directly to the β-catenin surface to inhibit its protein-protein interactions and downstream signaling. Here, we provide an account of the claimed (and some putative) small-mol. ligands of β-catenin from the literature. Through in silico anal., we show that most of these mols. contain promiscuous chem. substructures notorious for interfering with screening assays. Finally, and in line with this anal., we demonstrate using orthogonal biophys. techniques that none of the examined small mols. bind at the surface of β-catenin. While shedding doubts on their reported mode of action, this study also reaffirms β-catenin as a prominent target in drug discovery. The experimental process involved the reaction of 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1HPLC of Formula: 4857-06-1)

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.HPLC of Formula: 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Gilleran, John A.; Yu, Xin; Blayney, Alan J.; Bencivenga, Anthony F.; Na, Bing; Augeri, David J.; Blanden, Adam R.; Kimball, S. David; Loh, Stewart N.; Roberge, Jacques Y.; Carpizo, Darren R. published their research in Journal of Medicinal Chemistry in 2021. The article was titled 《Benzothiazolyl and Benzoxazoyl Hydrazones Function as Zinc Metallochaperones to Reactivate Mutant p53》.Application of 4857-06-1 The article contains the following contents:

We identified a set of thiosemicarbazone (TSC) metal ion chelators that reactivate specific zinc-deficient p53 mutants using a mechanism called zinc metallochaperones (ZMCs) that restore zinc binding by shuttling zinc into cells. We defined biophys. and cellular assays necessary for structure-activity relationship studies using this mechanism. We investigated an alternative class of zinc scaffolds that differ from TSCs by substitution of the thiocarbamoyl moiety with benzothiazoyl, benzoxazoyl, and benzimidazoyl hydrazones. Members of this series bound zinc with similar affinity and functioned to reactivate mutant p53 comparable to the TSCs. Acute toxicity and efficacy assays in rodents demonstrated C1 to be significantly less toxic than the TSCs while demonstrating equivalent growth inhibition. We identified C85 as a ZMC with diminished copper binding that functions as a chemotherapy and radiation sensitizer. We conclude that the benzothiazoyl, benzoxazoyl, and benzimidazoyl hydrazones can function as ZMCs to reactivate mutant p53 in vitro and in vivo. The experimental part of the paper was very detailed, including the reaction process of 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Application 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.Application of 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Prasoona, G.; Kishore, B.; Brahmeshwari, G. published their research in Russian Journal of Organic Chemistry in 2021. The article was titled 《A Simple and Efficient Four-Component One-Pot Synthesis of Novel 2-Aryl-3-benzimidazolyl-3,4-dihydroimidazo[4,5-b]indoles Catalyzed by Ceric Ammonium Nitrate in Aqueous Ethanol》.Reference of 1H-Benzo[d]imidazol-2-amine The article contains the following contents:

A simple and efficient protocol for the synthesis of benzimidazolylimidazo[4,5-b]indoles was developed through the condensation of 2-aminobenzimidazoles, aromatic aldehydes, ammonium acetate and isatins via multicomponent reaction strategy using ceric ammonium nitrate as catalyst. The key advantages of the four-component reaction were easy work-up, high yield, short reaction time and environmentally safe solvent. After reading the article, we found that the author used 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7Reference of 1H-Benzo[d]imidazol-2-amine)

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.Reference of 1H-Benzo[d]imidazol-2-amine

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Journal of Molecular Structure included an article by Abdulazeez, Ismail; Khaled, Mazen; Al-Saadi, Abdulaziz A.. Quality Control of 2-Chloro-1H-benzo[d]imidazole. The article was titled 《Impact of electron-withdrawing and electron-donating substituents on the corrosion inhibitive properties of benzimidazole derivatives: A quantum chemical study》. The information in the text is summarized as follows:

The role of substituents in the enhancement of corrosion inhibition effectiveness in some organic compounds has been the subject of several studies in recent years. Understanding the relationship between corrosion inhibition performance and electronic properties of the mol. shall facilitate the design of efficient inhibitors and reduce the burden of exptl. trials involved. In this study, quantum chem. calculations using d. functional theory (DFT) method were performed on benzimidazole and its derivatives involving various electron-withdrawing and electron-releasing substituents. Several reactivity indicators, such as frontier orbitals, energy gaps, electronegativity, electrophilicity and global hardness were calculated and correlated with available exptl. data. Frontier orbital energy gap predicted 2-nitrobenzimidazole to possess higher anti-corrosion properties, while electronegativity, electrophilicity and global hardness predicted 2-aminobenzimidazole to exhibit higher corrosion inhibition tendency. Results of mol. level interaction studies predicted that the adsorption of the mols. over the iron surface would take place preferentially through the nitrogen atoms of the imidazole ring and the carbon atoms of the benzene ring, resulting in the formation of Fe-N and Fe-C bonds with 2.00-2.40 Å bond distances which lie within the range of the chemisorption interaction. In the part of experimental materials, we found many familiar compounds, such as 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Quality Control of 2-Chloro-1H-benzo[d]imidazole)

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,Chaplais, Gerald; Fraux, Guillaume; Paillaud, Jean-Louis; Marichal, Claire; Nouali, Habiba; Fuchs, Alain H.; Coudert, Francois-Xavier; Patarin, Joel published 《Impacts of the Imidazolate Linker Substitution (CH3, Cl, or Br) on the Structural and Adsorptive Properties of ZIF-8》.Journal of Physical Chemistry C published the findings.HPLC of Formula: 16681-56-4 The information in the text is summarized as follows:

Zeolitic Imidazolate Frameworks (ZIFs) represent a thriving subclass of metal-organic frameworks (MOFs) owing to the large variety of their topologies, of which some of them are common with zeolites, and the ability to modulate the chem. of their frameworks as well as the hydrophobicity/hydrophilicity balance, making them perfect examples of the isoreticular chem. concept. One peculiar structural feature of ZIFs is their potential for structural transitions by rotation (or swing) of their linkers under external stimuli (guest adsorption, mech. constraints, etc.). This singular characteristic, often denominated “”swing effect”” or “”gate opening””, is related to flexible ZIFs. Our study focuses on the influence of the functional group (-CH3, -Cl, -Br) borne in position 2 by the imidazolate linker on the flexible/stiff nature of three isoreticular ZIFs with SOD topol. In the first part, we report the structures of ZIF-8_Cl and ZIF-8_Br, two halogenated analogs of the well-known ZIF-8 (herein named ZIF-8_CH3), thanks to synergistic contributions of powder X-ray diffraction and 13C MAS NMR spectroscopy. In both cases, a disorder of the linker is noted and characterized by two quasi-equal occupancies of the two linker subsets in the asym. unit. Exptl. nitrogen sorption measurements, performed at 77 K for the three isoreticular ZIFs, combined with first-principles mol. dynamics simulations bring to light the flexibility of ZIF-8_CH3 and ZIF-8_Cl and the stiffness of ZIF-8_Br.2-Bromo-1H-imidazole(cas: 16681-56-4HPLC of Formula: 16681-56-4) 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. HPLC of Formula: 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Correction: Substituent effects on the basicity (pKa) of aryl guanidines and 2-(arylimino)imidazolidines: correlations of pH-metric and UV-metric values with predictions from gas-phase ab initio bond lengths [Erratum to document cited in CA168:305952]》 was published in New Journal of Chemistry in 2017. These research results belong to Dardonville, Christophe; Caine, Beth A.; Navarro de la Fuente, Marta; Martin Herranz, Guillermo; Corrales Mariblanca, Beatriz; Popelier, Paul L. A.. Synthetic Route of C6H10N2O2S The article mentions the following:

In the original publication, there are errors in the acknowledgments section; the correction is provided here. In the experiment, the researchers used many compounds, for example, Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2Synthetic Route of C6H10N2O2S)

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. Synthetic Route of C6H10N2O2S 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

Quality Control of 2-Bromo-1H-imidazoleIn 2021 ,《Template-Mediated Control over Polymorphism in the Vapor-Assisted Formation of Zeolitic Imidazolate Framework Powders and Films》 was published in Angewandte Chemie, International Edition. The article was written by Tu, Min; Kravchenko, Dmitry E.; Xia, Benzheng; Rubio-Gimenez, Victor; Wauteraerts, Nathalie; Verbeke, Rhea; Vankelecom, Ivo F. J.; Stassin, Timothee; Egger, Werner; Dickmann, Marcel; Amenitsch, Heinz; Ameloot, Rob. The article contains the following contents:

The landscape of possible polymorphs for some metal-organic frameworks (MOFs) can pose a challenge for controlling the outcome of their syntheses. Demonstrated here is the use of a template to control in the vapor-assisted formation of zeolitic imidazolate framework (ZIF) powders and thin films. Introducing a small amount of either ethanol or DMF vapor during the reaction between ZnO and 4,5-dichloroimidazole vapor results in the formation of the porous ZIF-71 phase, whereas other conditions lead to the formation of the dense ZIF-72 phase or amorphous materials. Time-resolved in situ small-angle X-ray scattering reveals that the porous phase is metastable and can be transformed into its dense polymorph. This transformation is avoided through the introduction of template vapor. The porosity of the resulting ZIF powders and films was studied by N2 and Kr physisorption, as well as positron annihilation lifetime spectroscopy. The templating principle was demonstrated for other members of the ZIF family as well, including the ZIF-7 series, ZIF-8_Cl, and ZIF-8_Br. In addition to this study using 2-Bromo-1H-imidazole, there are many other studies that have used 2-Bromo-1H-imidazole(cas: 16681-56-4Quality Control of 2-Bromo-1H-imidazole) 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. Quality Control of 2-Bromo-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem