Tag: 100-200

COA of Formula: C7H6N4OIn 2020 ,《Polyurethane hot melt adhesive based on Diels-Alder reaction》 appeared in International Journal of Adhesion and Adhesives. The author of the article were Wu, Meiyin; Liu, Yuan; Du, Pengfei; Wang, Xinling; Yang, Bin. The article conveys some information:

Traditional hot melt adhesives are thermoplastic resins with non-covalent hydrogen bonds. In this letter, a polyurethane hot melt adhesive (CDI-PUR-DA) was synthesized via introducing thermally reversible covalent Diels-Alder adducts into the polyurethane main chain. Results from hydrogen NMR (NMR) anal. and an assessment of rheol. properties demonstrated that CDI-PUR-DA exhibited a much lower viscosity than a traditional hot melt adhesive. The viscosity of the polyurethane decreased to 4 Pa s at 110° due to rupture of Diels-Alder adducts. However, the viscosity returned to its initial value on cooling due to the regeneration of the Diels-Alder adducts. This approach provides a new method for preparing hot melt adhesives.Di(1H-imidazol-1-yl)methanone(cas: 530-62-1COA of Formula: C7H6N4O) 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.COA of Formula: C7H6N4O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

SDS of cas: 2403-66-9On March 31, 1987, Hasan, Mashooda; Latif, Farzana; Garcia Alvarez, Maria C. published an article in Journal of the Chemical Society of Pakistan. The article was 《Preparation, physical properties and nuclear magnetic resonance spectral studies of isomeric 2-(hydroxypropyl)benzimidazoles》. The article mentions the following:

Preparation, phys. properties and NMR spectral (1H and 13C) data of 2-[2-(hydroxypropyl)]- and 2-[3-(hydroxypropyl)]benzimidazoles and have been described. In the experiment, the researchers used many compounds, for example, 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9SDS of cas: 2403-66-9)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) 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. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. SDS of cas: 2403-66-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

COA of Formula: C3H3BrN2In 2006 ,《QSAR models based on quantum topological molecular similarity》 appeared in European Journal of Medicinal Chemistry. The author of the article were Popelier, P. L. A.; Smith, P. J.. The article conveys some information:

A new method called quantum topol. mol. similarity (QTMS) was fairly recently proposed [J. Chem. Inf. Comp. Sc., 41, 2001, 764] to construct a variety of medicinal, ecol. and phys. organic QSAR/QSPRs. QTMS method uses quantum chem. topol. (QCT) to define electronic descriptors drawn from modern ab initio wave functions of geometry-optimized mols. It was shown that the current abundance of computing power can be utilized to inject realistic descriptors into QSAR/QSPRs. In this article the authors study seven datasets of medicinal interest: the dissociation constants (pKa) for a set of substituted imidazolines, the pKa of imidazoles, the ability of a set of indole derivatives to displace [3H] flunitrazepam from binding to bovine cortical membranes, the influenza inhibition constants for a set of benzimidazoles, the interaction constants for a set of amides and the enzyme liver alc. dehydrogenase, the natriuretic activity of sulfonamide carbonic anhydrase inhibitors and the toxicity of a series of benzyl alcs. A partial least square anal. in conjunction with a genetic algorithm delivered excellent models. They are also able to highlight the active site, of the ligand or the mol. whose structure determines the activity. The advantages and limitations of QTMS are discussed. The experimental part of the paper was very detailed, including the reaction process of 2-Bromo-1H-imidazole(cas: 16681-56-4COA of Formula: 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. COA of Formula: C3H3BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Boehme, Matthias D.; Wilm, Lukas F. B.; Hepp, Alexander; Hahn, F. Ekkehardt published an article in 2021. The article was titled 《Regioselective Double Oxidative Addition of Bis-NHC Precursors》, and you may find the article in European Journal of Inorganic Chemistry.Category: imidazoles-derivatives The information in the text is summarized as follows:

The 4,4′-dimethylenebiphenyl linked sym. bis-(2-chlorobenzimidazole) (1) and the unsym. 2-chlorobenzimidazolium/2-chlorobenzimidazole [2(BF4)] have been reacted with one equiv of [Pd(PPh3)4] in oxidative addition reactions. For the sym. bis-NHC precursor 1, double metalation of both 2-chlorobenzimidazole sites to give the dinuclear bis-pNHC complex ([3][BF4]2) was observed The unsym. compound 2(BF4) was only metalated at the 2-chlorobenzimidazolium site with formation of the mononuclear NHC complex ([4][BF4]). The remaining 2-chlorobenzimidazole moiety was subsequently metalated in a second oxidative addition reaction with [M(PPh3)4] (M = Pd, Pt) to give the homobimetallic NHC/pNHC complex [5](BF4)2 (M = Pd) and the heterobimetallic complex [6](BF4)2 demonstrating the unique site-selective metalation of the bis-NHC precursor 2(BF4) by two consecutive oxidative additions 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 1923,King, Harold; Murch, Wm. O. published 《Bromination of glyoxaline-4-carboxanilide》.Journal of the Chemical Society, Transactions published the findings.SDS of cas: 16681-56-4 The information in the text is summarized as follows:

The object of this investigation was the preparation of 4-bromoglyoxaline-5-carboxylic acid (I) with the view of synthesizing xanthine by condensation of the ester with CO(NH2)2. The acid was obtained but the small yields have prevented attempts at the condensation. Two mols. Br react with glyoxaline-4-carboxanilide in glacial AcOH, giving a mixture of mono-, di- and tri-Br derivatives This is extracted with H2O on the boiling H2O bath. The aqueous solution deposits glyoxaline-4-carbox-p-bromoanilide, crystallizing from AcOH with 2 AcOH of crystallization, lost at 100° and then m. 273-4°. Hydrolysis gives I. 5-Bromoglyoxaline-4-carbox-p-bromoanilide (II), m. 245-6°, is then extracted with very dilute HCl. The residue is the 2,5-dibromo derivative (III), C10H6ON3Br3, which crystallines with 1 C2H4O2, and m. 257-8° (decomposition). Hydrolysis of III with HCl (sealed tube at 150° for 3 hrs.) gave p-BrC6H4NH2, and a mixture containing about 95% dichloro- and 5% dibromoglyoxaline, m. 184-5°. Hydrolysis of III with HBr gave a mixture of the 2,5-Br2 derivative and 2-bromoglyoxaline, m. 207°; Pauly’s reagent gives a deep orange color; picrate, yellow, m. 232° (decomposition); nitrate, decomposes violently 137°. 2,5-Dibromoglyoxaline nitrate-silver nitrate, 2C3H2N2Br2.AgNO3.HNO3. II is soluble in about 6 parts boiling AcOH. It is mixed with a very small amount of a compound containing about 50% Br and m. 247°. Hydrolysis of II with 24% HBr gives p-BrC6H4NH2 and 5-bromoglyoxaline-4-carboxylic acid, m. 265°, soluble in 50 parts boiling H2O, and forms a hydrochloride, nitrate, Ag salt, and gives a deep orange color with Pauly’s reagent. Et ester, m. 170-1°. With 30% HBr some 4-bromoglyoxaline was also isolated. Bromination of II gave III with some of the compound m. 247°. The results came from multiple reactions, including the reaction of 2-Bromo-1H-imidazole(cas: 16681-56-4SDS of cas: 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. SDS of cas: 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Synthesis and the reactions of 2,4,6-tris(ω-hydroxyalkyl)-1,3,5triazines》 was published in Bulletin of the Chemical Society of Japan in 1965. These research results belong to Nohira, Hiroyuki; Nishikawa, Yoshihiro; Furuya, Yoshiaki; Mukaiyama, Teruaki. Product Details of 2403-66-9 The article mentions the following:

From HO(CH2)nCN (I) and HCl were prepared the corresponding cyclic imino ethers HCl salts (II.HCl), which on treatment with Et3N gave the title compounds (III). The reactions of III with o-C6H4-(NH2)2 (IV) and 1,8-naphthalenediamine (V) were investigated. Treatment of Cl(CH2)3OH with KCN in EtOH-H2O (Aksnes and Prue, CA 53, 8004f) gave 30% I (n = 3), b11 1078°. A mixture of 22 g. Cl(CH2)4OH, 33 g. KCN, 50 ml. glycerol, and 25 ml. H2O heated and stirred 15 min. at 100-10°, cooled, and extracted with 4 50-ml. portions tetrahydrofuran (THF) gave 7.0 g. I (n = 4), b0.5 86-8°; when the distillation was carried out without extracting soon after the reaction was complete, almost 30% THF, b. 65-6° was formed as by-product. From Cl(CH2)5OH was similarly prepared 83% I (n = 5), b3 97-8°. Dry HCl passed into 300 ml. dry Et2O containing 8.5 g. I (n = 3) at 10-15° with cooling and the mixture let stand 2 days at room temperature in a stoppered flask gave 11.5 g. II (n = 3) HCl salt, m. 103-5°. Similar treatment of I (n = 4) with HCl but in more dilute (1.5-2.0%) Et2O solution gave 90% II (n = 4) HCl salt, m. 128-9°. Dry HCl passed into 150 ml. dry Et2O and 80 ml. dry glycol acetal-free dioxane containing 4.5 g. I (n = 5) with cooling and the mixture kept 4 days at room temperature, refluxed 3 hrs., and evaporated in vacuo gave 5.1 g. H (n = 5) HCl salt, m. 143-4°. Heating II.HCl 5 min. at 150-60° or refluxing them in PhMe gave the corresponding Cl(CH2)nCONH2 (VI). The following VI were prepared (n, % yield, and m.p. given): 3, 95, 97°; 4, 80, 78°; 5, 95, 102°. II.HCl (0.08 mole) and 16.0 g. Et3N in 80 ml. absolute THF let stand 3 days at room temperature in a stoppered flask with intermittent shaking and the solution filtered and fractionated gave the following III (n, % yield, and b.p./ mm. given): 3, 53, 196-8°/0.1; 4, 70, 207-9°/0.04; 5, 50, 21821°/0.01. III (n = 3) (0.5 g.) and 0.7 g. PhNCO in 10 ml. THF let stand 2 days and evaporated gave 1.1 g. VII, m. 124-5° (95% EtOH). III and 3 mol. equivalents IV or V heated at 220-30° (oil bath) under N evolution of NH3 ceased (15-60 min.) and the mixture cooled and washed with Et2O gave VIII and IX, resp. The following VIII and IX were prepared (n, % yield, and m.p. given): VIII: 3, 85, 160-1° (THF) (O-Ac derivative m. 88-9°); 4, 79, 1645° (THF) (O-Ac derivative m. 95-7°; O,N-di-Ac deriv, m. 68-9°); 5, 55, 106° (EtOAc) (O,N-di-Ac derivative m. 78-9°); IX: 3, 34, 145-6° (dioxane); 4, 45, 157-8° (THF); 5, 60, 185-7° (dioxane). The O-Ac derivatives of VIII were prepared by reaction of VIII and 1.2 mol. equivalents Ac2O in C2H5N at room temperature; the O,N-di-Ac derivatives of VIII were prepared by reaction of VIII and 2.5 mol. equivalents Ac2O in C5H5N at 100% III (n = 3) (0.5 g.) and 0.7 g. V heated 1 hr. at 250-60° (N atm.) and the mixture cooled and washed with Et2O gave 0.5 g. X, m. 143-4° (THF). Ir and uv data were given for III (n = 3, 4, and 5). 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: 2403-66-9Product Details of 2403-66-9)

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.
Product Details of 2403-66-9 However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903》 were Sharma, Swagat H.; Pablo, Juan Lorenzo; Montesinos, Monica Suarez; Greka, Anna; Hopkins, Corey R.. And the article was published in Bioorganic & Medicinal Chemistry Letters in 2019. Safety of 2-Chloro-1H-benzo[d]imidazole The author mentioned the following in the article:

The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biol. characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of I, a TRPC5 inhibitor that is active in multiple animal models of CKD. The results came from multiple reactions, including the reaction of 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Safety of 2-Chloro-1H-benzo[d]imidazole)

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.Safety of 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Analytical and Bioanalytical Chemistry Research included an article by Rajamohana, R.; Nayakib, S. Kothai; Swaminathanc, M.; Sivakumard, K.. Safety of 1H-Benzo[d]imidazol-2-amine. The article was titled 《pH independent complexation of 2-aminobenzimidazole with β-cyclodextrin》. The information in the text is summarized as follows:

The spectral characteristics of 2-aminobenzimidazole (2ABZ) in aqueous and ss-cyclodextrin media has been investigated using absorption, steady state and time resolved fluorescence techniques. The stoichiometric ratio of the inclusion complex of neutral and monocationic forms of 2ABZ in β-CDx medium is found to be 1:1. There is no significant differences between ground and the excited state pKa values of 2ABZ under both the media and thus the amino group of 2ABZ mol. is not much affected by the complexation process i.e., it lies outside the β-CDx cavity. Considering the shape and dimensions of β-CDx, it is clear that the 2ABZ mol. cannot be completely included in the β-CDx cavity. Because, the overall height of 2ABZ is 10.6 Å, but the overall height of β-CDx is only 7.8 Å. Hence, it is possible to locate half of the 2ABZ mol. only permitted inside the β-CDx cavity as interpreted using exptl. data. In the experiment, the researchers used 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7Safety 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.Safety of 1H-Benzo[d]imidazol-2-amine

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2014,Angewandte Chemie, International Edition included an article by Jacob, Nicholas T.; Lockner, Jonathan W.; Kravchenko, Vladimir V.; Janda, Kim D.. Safety of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate. The article was titled 《Pharmacophore Reassignment for Induction of the Immunosurveillance Cytokine TRAIL》. The information in the text is summarized as follows:

Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) is an immunosurveillance cytokine that kills cancer cells but demonstrates little toxicity against normal cells. While investigating the TRAIL-inducing imidazolinopyrimidinone TIC10, a misassignment of its active structure was uncovered. Syntheses of the two isomers, corresponding to the published and reassigned structures, are reported. The ability of each to induce TRAIL expression in macrophages was investigated and only the compound corresponding to the reassigned structure shows the originally reported activity; the compound corresponding to the published structure is inactive. Importantly, this structural reassignment has furnished a previously unknown antitumor pharmacophore. The results came from multiple reactions, including the reaction of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2Safety of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate)

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. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Safety of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Linker substituents control thermodynamic stability in metal organic frameworks》 was written by Novendra, Novendra; Marrett, Joseph M.; Katsenis, Athanassios D.; Titi, Hatem M.; Arhangelskis, Mihails; Friscic, Tomislav; Navrotsky, Alexandra. Formula: C3H3BrN2 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

We report the first systematic exptl. and theor. study of the relationship between the linker functionalization and the thermodn. stability of metal-organic frameworks (MOFs) using a model set of eight isostructural zeolitic imidazolate frameworks (ZIFs) based on 2-substituted imidazolate linkers. The frameworks exhibit a significant (30 kJ·mol-1) variation in the enthalpy of formation depending on the choice of substituent, which is accompanied by only a small change in molar volume. These energetics were readily reproduced by d. functional theory (DFT) calculations We show that these variations in the enthalpy of MOF formation are in linear correlation to the readily accessible properties of the linker substituent, such as the Hammett σ-constant or electrostatic surface potential. These results provide the first quantifiable relationship between the MOF thermodn. and the linker structure, suggesting a route to design and tune MOF stability. The results came from multiple reactions, including the reaction of 2-Bromo-1H-imidazole(cas: 16681-56-4Formula: 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. Formula: C3H3BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem