Tag: M.W=150-200

Li, Shi-Xiong published the artcileStructure, magnetism and oxygen reduction reaction in mixed-valent Cu(I)···Cu(II) complex supported by benzimidazole derivative, Product Details of C9H10N2O, the publication is Inorganica Chimica Acta (2021), 120356, database is CAplus.

Cu complexes have been extensively studied as synthetic models because of their different valences. Here, when the organic ligand (1-methyl-1H-benzo[d]imidazol-2-yl)methanol (HL) was used to react with Cu(ClO₄)₂·6H₂O in CH₃CN, the authors successfully obtained a mix valent copper complex [Cu^II(L¹)₂][Cu^I(HL)₂]·ClO₄ (1) under 60°C. The structure anal. suggested that the Cu1 ion was coordinated with two nitrogen atoms from two HL ligands, which two ligands without removing H ions. The Cu2 ion was coordinated with two oxygen ions and two nitrogen atoms from two L¹ ligands, which two ligands with removing H ions. The XPS test showed that the valence state of Cu1 ion was +1, and the Cu2 ion was +2. The magnetic susceptibility was exhibited ferrimagnetism with g = 2.04. The electrocatalytic results suggested that Cu^IICu^I species reacted with O₂ to give a superoxide radical intermediate for complex 1.

Inorganica Chimica Acta published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, Product Details of C9H10N2O.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Lane, Thomas J. published the artcileMetal binding of the benzimidazoles, Related Products of imidazoles-derivatives, the publication is Journal of the American Chemical Society (1960), 2994-7, database is CAplus.

The acid dissociation constants were determined potentiometrically for benzimidazole (I), 2-methylbenzimidazole (II), and 2-ethyl-benzimidazole in solutions of ionic strength 0.16M (NaNO₃) at 4 ± 1, 25 ± 0.1, and 35 ± 0.1°. The enthalpy changes ΔH⁰ were 8.7, 9.8, and 9.3 kcal./mole for the resp. compounds Formation constants were determined for Cu(II) with I by the Bjerrum potentiometric method in solutions of the same ionic strength at the 3 temperatures An upper limit was found for the value of the formation constant of Cu(II) with II at 4°. The formation constants for Cd with I and II were determined by a polarographic method in 50% aqueous EtOH at 25 ± 0.1°. The benzene portion of I appears to hinder coördination with Cu(II). Formation constants for Cu(II) with 2-(hydroxymethyl)benzimidazole and 1-methyl-2-(hydroxymethyl)benzimidazole show that the unsaturated N is the active site in the substituted I.

Journal of the American Chemical Society published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, Related Products of imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Smith, Leon M. II published the artcileNovel phenylalanine derived diamides as Factor XIa inhibitors, Application In Synthesis of 13682-33-2, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(2), 472-478, database is CAplus and MEDLINE.

The synthesis, structural activity relationships (SAR), and selectivity profile of a potent series of phenylalanine diamide FXIa inhibitors will be discussed. Exploration of P1 prime and P2 prime groups led to the discovery of compounds with high FXIa affinity, good potency in our clotting assay (aPPT), and high selectivity against a panel of relevant serine proteases as exemplified by compound (I). Compound I demonstrated good in vivo efficacy (EC₅₀ = 2.8 μM) in the rabbit elec. induced carotid arterial thrombosis model (ECAT).

Bioorganic & Medicinal Chemistry Letters published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C10H9NO4S, Application In Synthesis of 13682-33-2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Algul, Oztekin published the artcileSynthesis, characterization and genotoxicity of platinum(II) complexes with substituted benzimidazole ligands, Application In Synthesis of 7467-35-8, the publication is Turkish Journal of Chemistry (2005), 29(6), 607-615, database is CAplus.

Five cis-[Pt(II)Cl₂L_n] complexes with substituted benzimidazole ligands (n = 2, L = 2-ethyl-, 2-benzyl-, 2-phenoxymethyl-, 1-methyl-2-phenyl-benzimidazole; n = 1, L = 1-methyl-2-hydroxymethylbenzimidazole) were synthesized and characterized by elemental anal., and IR and ¹H-NMR spectra and evaluated for their in vitro genotoxic activities by Rec-Assay test. Based on the data obtained the Pt(II) complexes tested might be taken into consideration as promising antitumor compounds

Turkish Journal of Chemistry published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, Application In Synthesis of 7467-35-8.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Delgado, F. published the artcileNonpeptide angiotensin II receptor antagonists: synthesis and biological activity of 1H-imidazo and 1H-[1,2,3]-triazolo fused derivatives, Safety of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, the publication is Farmaco (1997), 52(3), 147-155, database is CAplus and MEDLINE.

Title compounds such as I [A = CH, CBu, N; R = H or RR = (CH:CH)₂; B = CH:CH, S; G = COOH, CN, 1H-tetrazol-5-yl] were prepared as angiotensin II receptor antagonists. Modification of the classical biphenyl moiety to a 4-arylthienyl fragment afforded interesting activities.

Farmaco published new progress about 79047-41-9. 79047-41-9 belongs to imidazoles-derivatives, auxiliary class Imidazole,Chloride,Alcohol, name is (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, and the molecular formula is C8H13ClN2O, Safety of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Chen, Yuqiu published the artcileMachine learning for the prediction of viscosity of ionic liquid-water mixtures, HPLC of Formula: 79917-90-1, the publication is Journal of Molecular Liquids (2022), 118546, database is CAplus.

In this work, a nonlinear model that integrates the group contribution (GC) method with a well-known machine learning algorithm, i.e., artificial neural network (ANN), is proposed to predict the viscosity of ionic liquid (IL)-water mixtures After a critical assessment of all data points collected from literature, a dataset covering 8,523 viscosity data points of IL-H₂O mixtures at different temperature (272.10 K-373.15 K) is selected and then applied to evaluate the proposed ANN-GC model. The results show that this ANN-GC model with 4 or 5 neurons in the hidden layer is capable to provide reliable predictions on the viscosities of IL-H₂O mixtures With 4 neurons in the hidden layer, the ANN-GC model gives a mean absolute error (MAE) of 0.0091 and squared correlation coefficient (R²) of 0.9962 for the 6,586 training data points, and for the 1,937 test data points they are 0.0095 and 0.9952, resp. When this nonlinear model has 5 neurons in the hidden layer, it gives a MAE of 0.0098 and R² of 0.9958 for the training dataset, and for the test dataset they are 0.0092 and 0.9990, resp. In addition, comparisons show that the nonlinear ANN-GC model proposed in this work has much better prediction performance on the viscosity of IL-H₂O mixtures than that of the linear mixed model.

Journal of Molecular Liquids published new progress about 79917-90-1. 79917-90-1 belongs to imidazoles-derivatives, auxiliary class Ionic Liquid,Ionic Liquid, name is 3-Butyl-1-methyl-1H-imidazol-3-ium chloride, and the molecular formula is C8H15ClN2, HPLC of Formula: 79917-90-1.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Castillo, Ivan published the artcileCopper(II) complexes of piperazine-derived tetradentate ligands and their chiral diazabicyclic analogues for catalytic phenol oxidative C-C coupling, HPLC of Formula: 4760-35-4, the publication is Inorganic Chemistry Communications (2013), 1-4, database is CAplus.

Reaction of the chiral ligands (1S,4S)-2,5-bis(6-methylpyridyl)-diazabicyclo[2.2.1]heptane (L¹) and (1S,4S)-2,5-bis(1-methyl-2-methylbenzimidazolyl)-diazabicyclo[2.2.1]heptane (L²) with CuCl₂ results in the hydroxo-bridged dicopper complexes [(L¹)Cu₂(μ-OH)(H₂O)Cl₃] (3), and [(L²)Cu₂(μ-OH)(H₂O)Cl₃] (4). Both chiral complexes were characterized spectroscopically, and 3 in the solid state by x-ray crystallog., confirming they are structurally related to their previously reported copper acetate analogs (1 and 2) due to their hydroxo-bridged bimetallic core. The achiral ligand analogs N,N’-bis(2-picolyl)piperazine (L³) and N,N’-bis(1-methyl-2-methylbenzimidazolyl)piperazine (L⁴) were employed to obtain the corresponding complexes with CuCl₂, affording the chloro-bridged [(L³)(CuCl)₂(μ-Cl)₂]_n (5) and [(L⁴)(CuCl)₂(μ-Cl)₂] (6), neither of which features a bridging hydroxo ligand; instead, complex 5 was structurally characterized as a coordination polymer. The acetate-derived complexes 1 and 2 are active in oxidative C-C coupling of 2,4-di-tert-butylphenol, while 3 and 4 have low activity; the achiral complexes 5 and 6, lacking a bridging hydroxo ligand, are inactive in this reaction.

Inorganic Chemistry Communications published new progress about 4760-35-4. 4760-35-4 belongs to imidazoles-derivatives, auxiliary class Chloride,Benzimidazole, name is 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, and the molecular formula is C9H9ClN2, HPLC of Formula: 4760-35-4.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Mamalis, P. published the artcileSome benziminazolylalanines, COA of Formula: C9H10N2O, the publication is Journal of the Chemical Society (1950), 1600-3, database is CAplus.

1-(Hydroxymethyl)benzimidazole (16 g.), added to 150 mL. SOCl₂ and refluxed 1 h., gives 17 g. 1-(chloromethyl)benzimidazole-HCl (I), m. 173-4° (decomposition). Na (2.3 g.) in 150 mL. EtOH, treated with 11.7 g. AcNHCH(CO₂Et)₂ and then with 10.8 g. I, boiled 2 h., the residual gum purified by passage of the C₆H₆ solution through Al₂O₃, and the yellow gum (10.7 g.) hydrolyzed by boiling 4 h. with 150 mL. concentrated HBr, gives the di-HBr salt, m. 192° (decomposition), of β-(1-benzimidazolyl)alanine, with 1 mol. H₂O, m. 196° (decompn); the H₂O is not removed on drying in vacuo (hydration seems to be a characteristic of this series of compounds). 5-Methylbenzimidazole (1 g.) in 15 mL. MeOH, treated with 1 mL. 40% HCHO and kept overnight, gives an inseparable mixture of 5- and 6-methyl-1-(hydroxymethyl)benzimidazole, m. 137-40°. 5,6-Dimethyl-1-(hydroxymethyl)benzimidazole m. 195-7° (decomposition); it decompose readily with liberation of HCHO. 2-Methyl- and 2-ethylbenzimidazoles do not form 1-hydroxymethyl derivatives and do not condense with CH₂:C(NHAc)CO₂H. The appropriate ο-C₆H₄(NH₂)₂ (0.1 mol.), heated 2 h. with 0.2 mol. HOCH₂CO₂H at 140-50°, gives 2-(hydroxymethyl)benzimidazoles: 1-Me, m. 145°, 70%; 4-Me, m. 198°, 75%; 5-Me, m. 202-3°, 70%; 5,6-di-Me derivative, m. 253-4°, 55%. 2-(Chloromethyl)benzimidazole-HCl (II), yellow, m. 229° (decomposition), 80%; 4-Me derivative, m. 251-2° (decomposition), 80%; 5-Me derivative, m. 216° (decomposition); 5,6-di-Me derivative, m. 282° (decomposition), 70%. 2-(Chloromethyl)benzimidazole (12.3 g.) and 16 g. AcNHCH(CO₂Et)₂ in 150 mL. EtOH containing 1.7 g. Na give a product which, extracted with 300 mL. boiling C₆H₆, give 1.5 g. Et α-acetamido-2-benzimidazolepropionate (III), m. 214°; the C₆H₆ extract, chromatographed on Al₂O₃ and eluted with 500 mL. 1:1 C₆H₆-AcOEt, gives 65% Et acetamido(2-benzimidazolylmethyl)malonate, m. 162-3°; II gives essentially the same results; hydrolysis of either compound with concentrated HBr gives β-(2-benzimidazolyl)alanine (IV), with 1 mol. H₂O, m. 210° (decomposition); HBr salt, m. 237° (decomposition). IV (1.4 g.) in 50 mL. boiling absolute EtOH, treated 1 h. with dry HCl and the residue warmed 1 h. with 20 mL. Ac₂O, gives 500 mg. III. 1-Methyl-2-(chloromethyl)benzimidazole (6.9 g.), 8.4 g. AcNHCH(CO₂Et)₂, and 100 mL. EtOH containing 0.85 g. Na give 9 g. Et acetamido(1-methyl-2-benzimidazolylmethyl)malonate, m. 133-4°; hydrolysis gives β-(1-methyl-2-benzimidazolyl)alanine, with 1 mol. H₂O, m. about 216-19° (decomposition). 4-(Chloromethyl)benzimidazole-HCl gives 40% Et α-acetamido-4-methyl-2-benzimidazolepropionate (V), m. 172°, which yields β-(4-methyl-2-benzimidazolyl)alanine (VI), with 1 mol. H₂O, m. 210° (decomposition). 5-Methyl-2-(chloromethyl)benzimidazole-HCl gives 50% of the 5-Me isomer of V, m. 209°; hydrolysis gives the 5-Me isomer of VI, with 1 mol. H₂O, m. 196° (decomposition) [HBr salt, m. 245° (decomposition); picrate, yellow, m. 208° (decomposition)]. 5,6-Dimethyl-2-(chloromethyl)benzimidazole-HCl gives Et α-acetamido-5,6-dimethyl-2-benzimidazolepropionate, with 1 mol. EtOH, m. 182°; hydrolysis gives β-(5,6-dimethyl-2-benzimidazolyl)alanine, with 2 mols. H₂O, m. 210° (decomposition). 5-Hydantoinpropionic acid (4 g.) and 2 g. ο-C₆H₄(NH₂)₂ in 20 mL. 4 N HCl, refluxed 1 h., give 5-[2-(2-benzimidazolyl)ethyl]hydantoin, m. 247-8° (decomposition); it could not be converted into the amino acid. 2-O₂NC₆H₄NHCH₂CH₂OH (6.1 g.), reduced in EtOH over Pd-C and the diamine in 40 mL. 4 N HCl heated 40 min. at 100° with 15 mL. HCO₂H, gives 75% 1-(2-hydroxyethyl)benzimidazole (VII), m. 108° (picrate, yellow, m. 205°); 2-Me derivative of VII, m. 148°, 65%; 2-Et derivative, m. 133°, 70%. 4,5,1,2-Me₂C₆H₂(NH₂)₂ and hippuric acid, fused 15 min. at 170°, give the Bz derivative, m. 233-4°, of 5,6-dimethyl-2-(aminomethyl)benzimidazole-2HCl, m. 266-8°. N-(2-Phthalimidoethyl)-ο-phenylenediamine (3 g.) and 12 mL. 95% HCO₂H, refluxed 1 h., give 80% 1-(2-phthalimidoethyl)benzimidazole, m. 211°; 2.5 g. and 25 mL. N₂H₄.H₂O, refluxed 2 h., give 750 mg. 1-(2-aminoethyl)benzimidazole-2HCl, m. 280°. These compounds showed no activity against a variety of organisms (Lactobacillus lactis, Mycobacterium tuberculosis, Trichomonas vaginatis, and Endamoeba histolytica). IV has low toxicity on i.v. administration to albino mice but proved irritant at the point of injection when administered either i.v. or s.c.; it has little action on the central nervous system.

Journal of the Chemical Society published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, COA of Formula: C9H10N2O.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Musser, John H. published the artcileN-[(Arylmethoxy)phenyl] carboxylic acids, hydroxamic acids, tetrazoles, and sulfonyl carboxamides. Potent orally active leukotriene D₄ antagonists of novel structure, Application In Synthesis of 4760-35-4, the publication is Journal of Medicinal Chemistry (1990), 33(1), 240-5, database is CAplus and MEDLINE.

Four types of N-[(arylmethoxy)phenyl] title compounds were prepared as leukotriene D₄ (I) antagonists. In the hydroxamic acid series, 3-(2-quinolinylmethoxy)benzeneacetohydroxamate II was the most potent inhibitor of I-induced bronchoconstriction with an oral ED₅₀ of 7.9 mg/kg. II also orally inhibited ovalbumin-induced bronchoconstriction in the guinea pig with an ED₅₀ of 3.6 mg/kg. In vitro against I-induced contraction of isolated guinea pig trachea pretreated with indomethacin and L-cysteine, II produced a pK_B value of 6.08. In the sulfonyl carboxamide series, N-[(4-methylphenyl)sulfonyl]-3-(2-quinolinylmethoxy)benzamide (III) was the most potent antagonist. III orally inhibited both I– and ovalbumin-induced bronchoconstriction with ED₅₀s of 0.4 and 20.2 mg/kg, resp. In vitro, against I-induced contraction of isolated guinea pig trachea, III produced a pK_B value of 7.78. In the carboxylic acid series, which served as intermediates for the above two series, 3-(2-quinolinyl)methoxybenzeneacetic acid IV was the most potent inhibitor of I-induced bronchoconstriction (99%, at 25 mg/kg, intraduodenally); however, the pK_B for IV was disappointing (5.79). In the tetrazole series the most potent inhibitor was 2-[[3-(1H-tetrazol-5-ylmethyl)phenoxy]methyl]quinoline (V). The resp. inhibitory ED₅₀s were 3.0 mg/kg vs. I and 17.5 mg/kg vs. ovalbumin. In the isolated guinea pig trachea, V produced a pK_B value of 6.70.

Journal of Medicinal Chemistry published new progress about 4760-35-4. 4760-35-4 belongs to imidazoles-derivatives, auxiliary class Chloride,Benzimidazole, name is 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, and the molecular formula is C9H9ClN2, Application In Synthesis of 4760-35-4.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Currie, Kevin S. published the artcileDiscovery of GS-9973, a Selective and Orally Efficacious Inhibitor of Spleen Tyrosine Kinase, Quality Control of 13682-33-2, the publication is Journal of Medicinal Chemistry (2014), 57(9), 3856-3873, database is CAplus and MEDLINE.

Spleen tyrosine kinase (Syk) is an attractive drug target in autoimmune, inflammatory, and oncol. disease indications. The most advanced Syk inhibitor, R406, (or its prodrug form fostamatinib), has shown efficacy in multiple therapeutic indications, but its clin. progress has been hampered by dose-limiting adverse effects that have been attributed, at least in part, to the off-target activities of R406. It is expected that a more selective Syk inhibitor would provide a greater therapeutic window. Herein the authors report the discovery and optimization of a novel series of imidazo[1,2-a]pyrazine Syk inhibitors. This work culminated in the identification of GS-9973, a highly selective and orally efficacious Syk inhibitor which is currently undergoing clin. evaluation for autoimmune and oncol. indications.

Journal of Medicinal Chemistry published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, Quality Control of 13682-33-2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem