Category: imidazoles-derivatives

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

Monsigny, Louis published the artcileActivated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde, Application of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Advanced Synthesis & Catalysis (2021), 363(19), 4590-4604, database is CAplus.

Two EWG-activated Hoveyda-Grubbs-type ruthenium complexes (Sil-II and Sil-II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a com. available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests disclosed that the bulkier NHC-ligand bearing catalyst Sil-II’ is visibly more stable and productive than its smaller NHC-analog Sil-II. Good application profile of catalyst Sil-II’ was confirmed in a set of diverse metathesis reactions including ring-closing metathesis (RCM) and cross-metathesis (CM) of complex polyfunctional substrates of medicinal chem. interest, including a challenging macrocyclization of the Pacritinib precursor. Compatibility of the new catalyst with various green solvents was checked and metathesis of Sildenafil and Tadalafil-based substrates was successfully conducted in acetone. The mechanism of Sil-II’ initiation has been investigated through kinetic experiments unveiling that the decrease of the steric hindrance of the chelating alkoxy moiety (from iPrO to EtO) favors the interchange initiation pathway over the typical dissociation pathway for other popular 2^nd generation Hoveyda-Grubbs catalysts.

Advanced Synthesis & Catalysis published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, Application of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

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

Jankowska-Anyszka, Marzena published the artcileSynthesis of a new class of ribose functionalized dinucleotide cap analogs for biophysical studies on interaction of cap-binding proteins with the 5′ end of mRNA, Synthetic Route of 359860-27-8, the publication is Organic & Biomolecular Chemistry (2011), 9(15), 5564-5572, database is CAplus and MEDLINE.

MRNAs of primitive eukaryotes such as Caenorhabditis elegans and Ascaris summ possess two different caps at their 5′ terminus. They have either a typical cap which consists of 7-methylguanosine linked via a 5′,5′-triphosphate bridge to the first transcribed nucleotide (MMG cap) or an atypical hypermethylated form with two addnl. Me groups at the N2 position (TMG cap). Studies on interaction between the 5′ end of mRNA and proteins that specifically recognize its structure have been carried out for several years and they often require chem. modified cap analogs. Here, we present the synthesis of five novel dinucleotide MMG and TMG cap analogs designed for binding studies using biophys. methods such as ESR and surface plasmon resonance. New analogs were prepared by derivatization of the 2′,3′-cis diol of the second nucleotide in the cap structure with levulinic acid, and coupling of the obtained acetal through its carboxylic group with 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino TEMPO), ethylenediamine (EDA) or (+)-biotinyl-3,6,9-trioxaundecanediamine (amine-PEO₃-biotin).

Organic & Biomolecular Chemistry published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C18H34N4O5S, Synthetic Route of 359860-27-8.

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

Borcard, Francoise published the artcileSurface modification of biomaterials for conjugation with human fetal osteoblasts, Recommanded Product: N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, the publication is Chimia (2013), 67(4), 213-217, database is CAplus and MEDLINE.

Surface functionalization of hydroxyapatite (HA) and β-tricalcium phosphate (TCP) bioceramics with chem. ligands containing a pyrrogallol moiety was developed to improve the adhesion of bone cell precursors to the biomaterials. Fast and biocompatible copper-free click reaction with azido-modified human fetal osteoblasts resulted in improved cell binding to both HA and TCP bioceramics, opening the way for using this methodol. in the preparation of cell-engineered bone implants.

Chimia published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C18H34N4O5S, Recommanded Product: N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide.

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

Barnhill, Hannah N. published the artcileDual modification of turnip yellow mosaic virus: synthesis of a biotinylated luminescent nanoparticle, Quality Control of 359860-27-8, the publication is PMSE Preprints (2006), 379-380, database is CAplus.

In this study, turnip yellow mosaic virus (TYMV) was employed as a scaffold for creating a bi-functional nanoparticle. TYMV is a 30 nm icosohedral virus with 60 asym. units and 180 protein subunits. As a proof concept that TYMV can be used as a multifunctional nanoparticle, luminescent metal complexes and the bio-active mol. biotin was conjugated onto the surface of TYMV using traditional bioconjugation methods. This study showed that the particle retains its integrity after the reaction and is stable to the attached functional groups. In addition, the two functional groups still retain their properties and can interact with each other on the surface as demonstrated by fluorescence resonance energy transfer.

PMSE Preprints published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C18H34N4O5S, Quality Control of 359860-27-8.

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

Sanghavi, N. M. published the artcileColorimetric determination of insoluble phosphomolybdic acid complexes of antihistamines, Safety of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, the publication is Indian Drugs (1980), 18(1), 25-8, database is CAplus.

Antihistamines viz. antazoeine-HCl [2508-72-7], dimenhydrinate [523-87-5], cyclizine-HCl [303-25-3], chlorcyclizine-HCl [14362-31-3] and diphenhydramine-HCl [147-24-0] are precipitated with phosphomolybdic acid; hydrazine hydrate quant. reduces the insoluble complexes to molybdenum blue which is measured colorimetrically. A linear relationship exists between the absorbance of the reaction product and the concentration of the drug present. Recovery from spiked tablet samples is 99.0-100.3%.

Indian Drugs published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C17H20ClN3, Safety of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride.

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

Owen, John T. R. published the artcileX-ray powder diffraction data for nine medicinal 2-imidazolines, Formula: C17H20ClN3, the publication is Journal – Association of Official Analytical Chemists (1981), 64(5), 1164-73, database is CAplus.

X-ray powder diffraction data for 9 2-imidazolines were obtained by the powder diffractometer and by the photog. Debye-Scherrer techniques. The data for individual 2-imidazolines are tabulated in terms of lattice spacings (d in Å) and the relative intensities of lines. The best method of packing for powder diffraction was investigated. It was advantageous to Cr Kα radiation in the Debye-Scherrer technique.

Journal – Association of Official Analytical Chemists published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C17H20ClN3, Formula: C17H20ClN3.

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

Berezin, Andrey A. published the artcileRing contraction of 1,3-diphenylbenzo[1,2,4]triazinyl radicals to 1,2-diphenylbenzimidazoles, Recommanded Product: 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is Organic & Biomolecular Chemistry (2014), 12(10), 1641-1648, database is CAplus and MEDLINE.

Reductive ring contraction of 1,3-diphenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yls (Blatter’s radicals) I (R = H, Cl, Br, I, CF₃, Ph, 2-furyl) using zinc powder (2 equivalent) in acetic acid heated to ca. 118 °C gives 1,2-diphenylbenzimidazoles II in high yield. 1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one and the zwitterionic tetraphenylhexaazaanthracene (TPHA) also undergo reductive ring contractions to give 1,2-diphenylbenzimidaz-6-ol and 1,2,6,7-tetraphenyl-1,7-dihydrobenzo[1,2-d:4,5-d’]diimidazole, resp. By using less zinc, the incomplete reduction of TPHA gave the stable organic radical 1,3,7,8-tetraphenyl-4,8-dihydro-1H-imidazo[4,5-g][1,2,4]benzotriazin-1-yl. Imidazolo-, oxazolo- and thiazolo-fused 1,2,4-benzotriazinyls all undergo zinc mediated ring contractions to give imidazolo-, oxazolo- and thiazolo-fused benzimidazoles in excellent yields.

Organic & Biomolecular Chemistry published new progress about 2622-67-5. 2622-67-5 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Benzene,Benzimidazole, name is 1,2-Diphenyl-1H-benzo[d]imidazole, and the molecular formula is C19H14N2, Recommanded Product: 1,2-Diphenyl-1H-benzo[d]imidazole.

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

Zakhari, N. Aziz published the artcileNonaqueous titration of halides of nitrogenous bases, using trifluoromethyl sulfonic acid, Application of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, the publication is Journal – Association of Official Analytical Chemists (1986), 69(4), 620-4, database is CAplus.

CF₃SO₃H (I) [1493-13-6] in AcOH was compared with HClO₄ as a titrant in 4 solvent systems: AcOH, Ac₂O, a mixture of both, and Me₂CO. The comparison was limited to the determination of halides of nitrogenous bases with and without the use of Hg(AcO)₂  [1600-27-7]. The results for the visual titrations showed that both acids are comparable titrants. However, I was superior to HClO₄ in potentiometric titrations carried out in AcOH-Ac₂O mixtures Moreover, the nonoxidizing properties exhibited by I were advantageous over HClO₄ in the visual detection of end points in the titration of phenothiazine derivatives in anhydrous AcOH using crystal violet indicator.

Journal – Association of Official Analytical Chemists published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C30H40N2O4, Application of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride.

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

Marciniec, Barbara published the artcileThermal study of four irradiated imidazoline derivatives in solid state, HPLC of Formula: 2508-72-7, the publication is Journal of Thermal Analysis and Calorimetry (2007), 88(2), 337-342, database is CAplus.

Four imidazoline derivatives: antazoline (AN), naphazoline (NN), tymazoline (TM), xylometazoline (XM), in the form of hydrochlorides in solid phase have been subjected to high energy e-beam irradiation from an accelerator (≈10 MeV) at a dose varied from 25 to 200 kGy. The effects of the irradiation have been assessed by DSC, X-ray diffraction, FTIR, EPR and TLC. The standard sterilization dose of 25 kGy has been found to produce changes in the properties of one derivative (XM), two other ones (AN and TM) have been found sensitive to doses >100 kGy, whereas NN has been resistant to irradiation in the whole range studied (25-200 kGy). EPR results indicated that the changes taking place in the therapeutic substances studied are related to radical formation. The irradiation induced changes in color, a decrease or increase in the m.p., changes in the XRD pattern, small changes in the shape of FTIR peaks and the presence of radiolysis products. The XM compounds cannot be sterilized by irradiation because of the radiation induced changes in its physico-chem. properties.

Journal of Thermal Analysis and Calorimetry published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C17H20ClN3, HPLC of Formula: 2508-72-7.

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