Category: 7467-35-8

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

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

Bevilacqua, Valentina published the artcileCopper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media, Related Products of imidazoles-derivatives, the publication is Angewandte Chemie, International Edition (2014), 53(23), 5872-5876, database is CAplus and MEDLINE.

The concept of chelation-assisted copper catalysis was employed for the development of new azides that display unprecedented reactivity in the copper(I)-catalyzed azide-alkyne [3+2] cycloaddition (CuAAC) reaction. Azides that bear strong copper-chelating moieties were synthesized; these functional groups allow the formation of azide copper complexes that react almost instantaneously with alkynes under diluted conditions. Efficient ligation occurred at low concentration and in complex media with only one equivalent of copper, which improves the biocompatibility of the CuAAC reaction. Furthermore, such a click reaction allowed the localization of a bioactive compound inside living cells by fluorescence measurements.

Angewandte Chemie, International Edition 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

Yoshikawa, Masato published the artcileDesign and synthesis of potent and selective pyridazin-4(1H)-one-based PDE10A inhibitors interacting with Tyr683 in the PDE10A selectivity pocket, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Bioorganic & Medicinal Chemistry (2016), 24(16), 3447-3455, database is CAplus and MEDLINE.

Utilizing structure-based drug design techniques, we designed and synthesized phosphodiesterase 10A (PDE10A) inhibitors based on pyridazin-4(1H)-one. These compounds can interact with Tyr683 in the PDE10A selectivity pocket. Pyridazin-4(1H)-one derivative 1 was linked with a benzimidazole group through an alkyl spacer to interact with the OH of Tyr683 and fill the PDE10A selectivity pocket. After optimizing the linker length, we identified 1-(cyclopropylmethyl)-5-[3-(1-methyl-1H-benzimidazol-2-yl)propoxy]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (16f) as having highly potent PDE10A inhibitory activity (IC₅₀ = 0.76 nM) and perfect selectivity against other PDEs (>13,000-fold, IC₅₀ = >10,000 nM). The crystal structure of 16f bound to PDE10A revealed that the benzimidazole moiety was located deep within the PDE10A selectivity pocket and interacted with Tyr683. Addnl., a bidentate interaction existed between the 5-alkoxypyridazin-4(1H)-one moiety and the conserved Gln716 present in all PDEs.

Bioorganic & Medicinal 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 C19H14N2, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

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

Klock, Cornelius published the artcileDiscovery of Potent and Specific Dihydroisoxazole Inhibitors of Human Transglutaminase 2, COA of Formula: C9H10N2O, the publication is Journal of Medicinal Chemistry (2014), 57(21), 9042-9064, database is CAplus and MEDLINE.

Transglutaminase 2 (TG2) is a ubiquitously expressed enzyme that catalyzes the posttranslational modification of glutamine residues on protein or peptide substrates. A growing body of literature has implicated aberrantly regulated activity of TG2 in the pathogenesis of various human inflammatory, fibrotic, and other diseases. Taken together with the fact that TG2 knockout mice are developmentally and reproductively normal, there is growing interest in the potential use of TG2 inhibitors in the treatment of these conditions. Targeted-covalent inhibitors based on the weakly electrophilic 3-bromo-4,5-dihydroisoxazole (DHI) scaffold have been widely used to study TG2 biol. and are well tolerated in vivo, but these compounds have only modest potency, and their selectivity toward other transglutaminase homologs is largely unknown. In the present work, we first profiled the selectivity of existing inhibitors against the most pertinent TG isoforms (TG1, TG3, and FXIIIa). Significant cross-reactivity of these small mols. with TG1 was observed Structure-activity and -selectivity analyses led to the identification of modifications that improved potency and isoform selectivity. Preliminary pharmacokinetic anal. of the most promising analogs was also undertaken. Our new data provides a clear basis for the rational selection of dihydroisoxazole inhibitors as tools for in vivo biol. investigation.

Journal of Medicinal 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, COA of Formula: C9H10N2O.

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

Shevtsova, I. I. published the artcileCoordination compounds of copper salts and silver salts with some benzimidazole and benzothiazole derivatives and their antimicrobic properties, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Antibiotiki (Kiev) (1970), 44-8, database is CAplus.

Among 26 coordination compounds studied, 2 complexes of AgNO3 with 2-methylbenzothiazole and 2-(hydroxymethyl)benzothiazole had a high antiinfusorial activity. The action of all compounds on Paramecium caudatum is shown. Four of the complexes prevented mold growth on grains.

Antibiotiki (Kiev) 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 C7H8BClO2, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

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

Kankate, Rani S. published the artcileMicrowave assisted synthesis, antifungal evaluation and molecular docking of benzimidazole derivatives, Application In Synthesis of 7467-35-8, the publication is Pharma Chemica (2014), 6(6), 396-405/1-396-405/10, 10 pp., database is CAplus.

A novel series of benzimidazole derivatives, carrying biphenyl carbonyl piperazine moiety based on an initial design by mol. docking study of this scaffold at the active site of the fungal enzyme of cytochrome P 450 family, lanosterol 14 α-demethylase (CYP51) was synthesized by microwave irradiation The screening of the synthesized compounds for in vitro antifungal activity against Candida albicans revealed activity for many compounds as comparable to that of ketoconazole.

Pharma Chemica 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

Kankate, Rani S. published the artcileSynthesis and in vitro antifungal evaluation of benzoimidazolyl-piperazinyl-phenylmethanone derivatives, HPLC of Formula: 7467-35-8, the publication is Oriental Journal of Chemistry (2014), 30(4), 1855-1863, database is CAplus.

A series of [(benzimidazolylalkyl)piperazinyl]phenylmethanone derivatives I [R¹ = H, Cl, R² = H, Me, Et, R³ = H, Me, Ph] was synthesized by microwave irradiation and evaluated for in vitro antifungal activity using ketoconazole as the standard Among the tested compounds, benzimidazole derivatives with an N-1 Me, a C2 asym. center and C5 chlorine substitution showed good antifungal activity against the C. albicans strain using the turbidimetric method.

Oriental 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, HPLC of Formula: 7467-35-8.

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

Verma, Raman K. published the artcileDesign, synthesis and computational validation of novel benzimidazole/indole-based PPARα and PPARγ partial agonists, HPLC of Formula: 7467-35-8, the publication is Journal of Chemical Sciences (Bangalore, India) (2013), 125(6), 1555-1571, database is CAplus.

The design and synthesis of benzimidazolyl and indolyl linked α-alkoxy phenylpropanoic acid derivatives and the β-keto ester analogs in an effort to develop novel peroxisome proliferator activated receptors ligands expected to exhibit PPARα and PPARγ partial agonism in the management of hyperglycemia and hyperlipidemia for the treatment of type 2 diabetes is reported. Computational validation of the designed mols. through activity prediction and docking studies showed expected results.

Journal of Chemical Sciences (Bangalore, India) 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 C9H17NO, HPLC of Formula: 7467-35-8.

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

Garcia-Alvarez, Ana C. published the artcileSelf-assembled nickel cubanes as oxygen evolution catalysts, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(69), 8608-8611, database is CAplus and MEDLINE.

Ni₄O₄ cubanes [(μ₃-L¹O)NiCl(MeOH)]₄ and [(μ₃-L²O)NiCl(H₂O)]₄ (L¹OH = 1-H-2-benzimidazolylmethanol, L²OH = 1-methyl-2-benzimidazolylmethanol) self-assemble from com. available 1-H- and 1-methyl-2-benzimidazolylmethanol and NiCl₂·6H₂O in high yields under mild conditions. Both complexes were characterised spectroscopically and by X-ray crystallog. The cubanes oxidise water electrocatalytically to dioxygen at neutral pH in aqueous potassium phosphate buffer solutions

Chemical Communications (Cambridge, United Kingdom) 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 of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

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