Category: imidazoles-derivatives

In 2022,Gougoula, Eva; Cummings, Charlotte N.; Medcraft, Chris; Heitkaemper, Juliane; Walker, Nicholas R. published an article in Physical Chemistry Chemical Physics. The title of the article was 《Microwave spectra, molecular geometries, and internal rotation of CH3 in N-methylimidazole···H2O and 2-methylimidazole···H2O complexes》.Safety of 1-Methyl-1H-imidazole The author mentioned the following in the article:

Broadband microwave spectra have been recorded between 7.0 and 18.5 GHz for N-methylimidazole···H2O and 2-methylimidazole···H2O complexes. Each complex was generated by co-expansion of low concentrations of methylimidazole and H2O in argon buffer gas. The rotational spectra of five isotopologues of each complex have been assigned and analyzed to determine rotational constants (A0, B0, C0), centrifugal distortion constants (DJ, DJK) and parameters that describe the internal rotation of the CH3 group. The results allow the determination of parameters in the (r0) mol. geometry of each complex. H2O is the hydrogen bond donor and the pyridinic nitrogen of imidazole is the hydrogen bond acceptor in each case. The ∠(O-Hb···N3) angles are 177(5)° and 166.3(28)° for N-methylimidazole···H2O and 2-methylimidazole···H2O resp. These results are consistent with the presence of a weak electrostatic interaction between the oxygen atom of H2O and the hydrogen atom (or CH3 group) attached to the C2 carbon atom of imidazole, and with the results of d. functional theory calculations The (V3) barrier to internal rotation of the CH3 group within N-methylimidazole···H2O is essentially unchanged from the value of this parameter for the N-methylimidazole monomer. The same parameter is significantly higher for the 2-methylimidazole···H2O complex than for the 2-methylimidazole monomer as a consequence of the weak electrostatic interaction between the O atom and the CH3 group of 2-methylimidazole. The experimental part of the paper was very detailed, including the reaction process of 1-Methyl-1H-imidazole(cas: 616-47-7Safety of 1-Methyl-1H-imidazole)

1-Methyl-1H-imidazole(cas: 616-47-7) is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate.Safety of 1-Methyl-1H-imidazole

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

In 2022,Anila, Sebastian; Suresh, Cherumuttathu H.; Schaefer, Henry F. III published an article in Journal of Physical Chemistry A. The title of the article was 《Demarcating Noncovalent and Covalent Bond Territories: Imine-CO2 Complexes and Cooperative CO2 Capture》.Reference of 1H-Imidazol-2-amine The author mentioned the following in the article:

Chem. bond territory is rich with covalently bonded mols. wherein a strong bond is formed by equal or unequal sharing of a quantum of electrons. The noncovalent version of the bonding scenarios expands the chem. bonding territory to a weak domain wherein the interplay of electrostatic and π-effects, dipole-dipole, dipole-induced dipole, and induced dipole-induced dipole interactions, and hydrophobic effects occur. Here we study both the covalent and noncovalent interactive behavior of cyclic and acyclic imine-based functional mols. (XN) with CO2. All parent XN systems preferred the formation of noncovalent (nc) complex XN···CO2, while more saturated such systems (XN′) produced both nc and covalent (c) complexes XN′+-(CO2)-. In all such cases, crossover from an nc to c complex is clearly demarcated with the identification of a transition state (ts). The complexes XN′···CO2 and XN′+-(CO2)- are bond stretch isomers, and they define the weak and strong bonding territories, resp., while the ts appears as the demarcation point of the two territories. Cluster formation of XN with CO2 reinforces the interaction between them, and all become covalent clusters of general formula (XN+-(CO2)-)n. The pos. cooperativity associated with the NH···OC hydrogen bond formation between any two XN′+-(CO2)- units strengthened the N-C coordinate covalent bond and led to massive stabilization of the cluster. For instance, the stabilizing interaction between the XN unit with CO2 is increased from 2-7 kcal/mol range in a monomer complex to 14-31 kcal/mol range for the octamer cluster (XN′+-(CO2)-)8. The cooperativity effect compensates for the large reduction in the entropy of cluster formation. Several imine systems showed the exergonic formation of the cluster and are predicted as potential candidates for CO2 capture and conversion. In the part of experimental materials, we found many familiar compounds, such as 1H-Imidazol-2-amine(cas: 7720-39-0Reference of 1H-Imidazol-2-amine)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Reference of 1H-Imidazol-2-amine

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

《Proton transfer dynamics in the aprotic proton accepting solvent 1-methylimidazole》 was written by Thomaz, Joseph E.; Walker, Alice R.; Van Wyck, Stephen J.; Meisner, Jan; Martinez, Todd J.; Fayer, Michael D.. Related Products of 616-47-7 And the article was included in Journal of Physical Chemistry B in 2020. The article conveys some information:

The dynamics of proton transfer to the aprotic solvent 1-methylimidazole (MeIm, proton acceptor) from the photoacid 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (HPTS) was investigated using fast fluorescence measurements. The closely related mol., 8-methoxypyrene-1,3,6-trisulfonic acid trisodium salt (MPTS), which is not a photoacid, was also studied for comparison. Following optical excitation, the wavelength-dependent population dynamics of HPTS in MeIm resulting from the deprotonation process were collected over the entire fluorescence emission window. Anal. of the time-dependent fluorescence spectra revealed four distinct fluorescence bands that appear and decay on different time scales. We label these four states as protonated (P), associated I (AI), associated II (AII), and deprotonated (D). We find that the simple kinetic scheme of P → AI → AII → D is not consistent with the data. Instead, the kinetic scheme that describes the data has P decaying into AI, which mainly goes on to deprotonation (D), but AI can also feed into AII. AII can return to AI or decay to the ground state, but does not deprotonate within exptl. error. Quantum chem. and excited state QM/MM Born-Oppenheimer mol. dynamics simulations indicate that AI and AII are two H-bonding conformations of MeIm to the HPTS hydroxyl, axial, and equatorial, resp. After reading the article, we found that the author used 1-Methyl-1H-imidazole(cas: 616-47-7Related Products of 616-47-7)

1-Methyl-1H-imidazole(cas: 616-47-7) is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate.Related Products of 616-47-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem