Category: 7467-35-8

Sharma, Pankaj published the artcileSynthesis and biological evaluation of new benzimidazole-thiazolidinedione hybrids as potential cytotoxic and apoptosis inducing agents, HPLC of Formula: 7467-35-8, the publication is European Journal of Medicinal Chemistry (2016), 608-621, database is CAplus and MEDLINE.

A series of new benzimidazole-thiazolidinedione hybrids was synthesized and evaluated for their cytotoxic potential against a selected human cancer cell lines of prostate (PC-3 and DU-145), breast (MDA-MB-231), lung (A549) and a normal breast epithelial cells (MCF10A). Among the tested compounds, I exhibited promising cytotoxicity with IC₅₀ value of 11.46 ± 1.46 μM on A549 lung cancer cell line and did not show significant toxicity on normal MCF10A cells. Lung cancer cells (A549) was used to know the mechanism of cell growth inhibition and apoptosis inducing effect with compound I. The treatment of A549 cells with I showed typical apoptotic morphol. like cell shrinkage, chromatin condensation and horseshoe shaped nuclei formation. Flow-cytometry anal. revealed the G2/M phase of cell cycle arrest in a dose dependent manner. Preliminary mechanistic studies suggested that the cell migration was inhibited through the disruption of F-actin protein. Acridine orange-ethidium bromide (AO-EB), DAPI, annexin V-FITC/propidium iodide, rhodamine-123 and MitoSOX assays suggested the induction of apoptosis in A549 cells by compound I.

European 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 C9H21NO3, HPLC of Formula: 7467-35-8.

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

Alasmary, Fatmah A. S. published the artcileSynthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents, Quality Control of 7467-35-8, the publication is Molecules (2015), 20(8), 15206-15223, database is CAplus and MEDLINE.

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with min. inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds had some common features; three possess 5-halo substituents; two were derivatives of (S)-2-ethanaminebenzimidazole; and the others were derivatives of one 2-(chloromethyl)-1H-benzo[d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives were considered as promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.

Molecules 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, Quality Control of 7467-35-8.

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

Artemenko, M. V. published the artcileComplex formation in the cupric nitrate-1-methyl-2-(hydroxymethyl)benzimidazole-methanol system, Synthetic Route of 7467-35-8, the publication is Zhurnal Neorganicheskoi Khimii (1967), 12(11), 3055-61, database is CAplus.

The complex formation of Cu(NO3)2 with 1-methyl-2-(hydroxymethyl)benzimidazole (I) in MeOH was studied by means of various optical methods. Four complex compounds, 2 addition products with the molar ratio of Cu:I = 1:1 and 1:3 and the other 2 mixed chelate alcoholates with 1:1 and 1:2 composition, were found. On the basis of the anal. the absorption spectra of the isomolar series of the solutions were decomposed into sep. Gaussian components. The application of crystal field theory established that these complex compounds have a tetragonal bipyramidal configuration. The optical characteristics for the detected bands of these complex compounds are given. The Me group in the 1 position in the I mol. has no influence on the composition and optical characteristics of the complex compounds

Zhurnal Neorganicheskoi Khimii 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, Synthetic Route of 7467-35-8.

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

Artemenko, M. V. published the artcileComplexes of copper salts with 2-(hydroxymethyl)benzimidazole and 1-methyl-2-(hydroxymethyl)benzimidazole, Recommanded Product: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Ukrainskii Khimicheskii Zhurnal (Russian Edition) (1966), 32(6), 560-6, database is CAplus.

2-(Hydroxymethyl)benzimidazole (ROH) and 1-methyl-2-(hydroxymethyl)benzimidazole (R’OH) react with Cu salts and an equimolar amount of PhNMe₂ in MeOH to form the following compounds (formula and m.p. given): ROCuCl, 216°; ROCuBr, 196°; R’OCuCl, 224°; R’ OCuBr, 223°; R’ OCuONO₂, 231°. The following were prepared by grinding together and adding MeOH or by mixing solutions of the components in MeOH solution: ROCuOAc, over 300°; R’ OCuOAe, 219°; 2ROH.Cu(NO₃)₂. MeOH (heating to 80° forms 2ROH. Cu(NO₃)₂, m. 203°); 2ROH.CuSO₄, over 250°; 3ROH.CuSO₄, over 250°; R’ OH.R’ OCuCl, 178°; R’ OH.R’ OCuBr, 196°; R’ OH.R’ OCuONO₂, 218°; 2R’ OH.Cu(NO₃)₂, 172°; 3R’OH.CuSO₄, 154°. ROH and CuSO₄ form ROH.CuSO₄4H₂O, m. 234°, in H₂O solution Dehydration yields ROH.-CuSO₄, m. 234°. Salts of ROH and R’ OH after grinding with Cu salts, solution in MeOH, and precipitation with Et₂O, form (ROH₂)₂(CuBr₄), m. 126°; (R’ OH₂)₂(CuCl₄), m. 166°; and (R’ OH₂)₂(CuBr₄), m. 158°. R’OH and Cu(OCH₂CH₂NH₂)₂ (CA 59, 8340h) in MeOH form R’ OCuOH, m. 142°.

Ukrainskii Khimicheskii Zhurnal (Russian 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, Recommanded Product: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

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

Valdez-Padilla, David published the artcileSynthesis and antiprotozoal activity of novel 1-methylbenzimidazole derivatives, Category: imidazoles-derivatives, the publication is Bioorganic & Medicinal Chemistry (2009), 17(4), 1724-1730, database is CAplus and MEDLINE.

In this paper are reported the synthesis and antiprotozoal activity in vitro of 24 1-methylbenzimidazole derivatives (13-36) substituted at position 2 with aminocarbonyl, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl, ethoxycarbonyl, 1-hydroxyethyl and acetyl groups, some of them with chlorine atoms at the benzenoid ring. Compounds 13-36 were more active than metronidazole, the choice drug against Giardia intestinalis and most of them against Trichomonas vaginalis. The most active group of compounds for both parasites was that with a 2-ethoxycarbonyl group (16, 22, 28, 34), independently of the substitution pattern at the benzenoid ring.

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 C13H10F2, Category: imidazoles-derivatives.

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

Dubey, P. K. published the artcileAlternate method for the synthesis of N-alkyl/aralkyl-2-(α-hydroxyalkyl/aralkyl)benzimidazoles via regiospecific acetylation, Name: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Synthetic Communications (2007), 37(10), 1675-1681, database is CAplus.

Acetylation of 1H-2-(α-hydroxyalkyl/aryl)benzimidazoles with Ac₂O results in the regiospecific formation of O-acetoxy derivative, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl derivatives The latter, on hydrolysis in an aqueous basic medium, results in the title compounds in good yields in high purity. Alternatively, the title compounds was also obtained by reduction of 1-substituted-2-acetyl/benzoylbenzimidazoles using NaBH₄.

Synthetic Communications 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, Name: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

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

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

Bednyagina, N. P. published the artcileHydrolytic cleavage of some sulfones of heterocyclic series. VI. Synthesis and properties of p-nitrophenylsulfonyl-N-methylbenzimidazolylmethane and p-nitrophen ylsulfonylbenzothiazolylmethane, COA of Formula: C9H10N2O, the publication is Zhurnal Obshchei Khimii (1960), 3193-6, database is CAplus.

cf. CA 51, 5086a; 53, 21971c; 54, 509i. 2-(Hydroxymethyl)benzimidazole and MeI in aqueous alc. NaOH gave 60-5% 1-methyl-2-(hydroxymethyl)benzimidazole, m. 125-30°, which with SOCl₂ gave 100% 1-methyl-2-(chloromethyl)benzimidazole-HCl, m. 195-6°; base m. 94°. This with p-O₂NC₆H₄SNa in EtOH gave p-nitrophenyl 2-(1-methylbenzimidazolyl)methyl sulfide, m. 154-5°; p-nitrophenyl 2-benzimidazolyl sulfide prepared similarly, m. 214-17°, yielded the above sulfide after treatment with MeI as above. The sulfide and KMnO₄ in AcOH gave the sulfone, m. 223-5°. 2-(Chloromethyl)benzothiazole and p-O₂NC₆H₄SNa gave p-nitrophenyl 2-benzothiazolylmethyl sulfide, m. 129-30°, which with KMnO₄ in AcOH gave the sulfone, m. 210-12°. Both the sulfones were unaffected by hot 2N HCl in 2 hrs.

Zhurnal Obshchei Khimii 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

Zakharova, N. A. published the artcileImidazole derivatives. X. Acylation of 2-hydroxymethylbenzimidazole and the products of its methylation, Quality Control of 7467-35-8, the publication is Zhurnal Obshchei Khimii (1953), 1225-30, database is CAplus.

cf. ibid. 957-63. Acylation of 2-(hydroxymethyl)benzimidazole (I) occurs primarily at the HO group and only later does the formation of diacyl derivatives take place, where the 2nd acyl group is bound to the hetero-N atom. The N-Me compounds yield only monoacyl derivatives at the HO group. Hydrolysis of 2-(chloromethyl)benzimidazole gave 65-73.6% I. I (5 g.), 5.6 ml. MeI, and 5 ml. MeOH heated in sealed tube 5 hrs. at 70-90° gave 6.35 g. solid 1-methyl-2-hydroxymethylbenzimidazole-HI and 1-methyl-2-(hydroxymethyl)benzimidazole methiodide. Treated with cold aqueous NH₄OH and extraction of the residue with dry C₆H₆ left behind 1.3 g. 1-methyl-2-hydroxymethylbenzimidazole methiodide (IA), m. 187-8° (from absolute EtOH). The solution after evaporation was treated with aqueous NH₄OH and C₆H₆ to obtain addnl. amounts IA (total yield 20.35%). The C₆H₆ extracts gave 20.1% 1-methyl-2-hydroxymethylbenzimidazole, m. 146-7° (from C₆H₆); HCl salt, m. 189-90°; HI salt, solid without definite m.p. Methylation of I at 150° gave 1,2-dimethylbenzimidazole methiodide, m. 258-9°, which is also obtained from 2-methylbenzimidazole under similar conditions. I (7 g.) heated on a steam bath with 9.45 ml. Ac₂O and 10 ml. AcOH 30-40 min. gave 98.7% crude O-acetyl derivative (IB) of I, m. 163-4° (from C₆H₆ or H₂O); I is regenerated by refluxing with 0.1N HCl or NaOH; heating with AcOH causes no change, but refluxing 30 min. with Ac₂O gave the O,1-diacetyl derivative (IC) of I, m. 97-8°. IB in EtOH treated with aqueous AgNO₃ gave the Ag salt, C₁₀H₉.O₂N₂Ag. I (0.5 g.) in 150 ml. hot H₂O, was chilled and treated with 4 ml. 25% NaOH followed by 52.1 ml. 0.1N iodine in KI yielding a precipitate of 0.82 g. 1-iodo-O-acetyl derivative of I, m. 164° (it is readily analyzed by treatment with 10% KI in 2N HCl, warming and titrating the liberated iodine). I heated 20 min. to 100° with AcONa-Ac₂O gave 84% IC, m. 98-9.5° (from C₆H₆-petr. ether), which boiled with H₂O 10 min. gave 100% IB. The 1-Me derivative (II) of I heated 1 hr. at 100° with excess Ac₂O and AcOH gave 63% of the 1-methyl-O-acetyl derivative of I, m. 76-8°. IA similarly heated with Ac₂O-AcOH 1.5 hrs. gave a red solid, while the filtrate diluted with dry Et₂O gave a yellow oil, which with Et₂O-CHCl₃ gave colorless solid, decompose 256-8°, containing 43.1% iodine. The red solid treated with CHCl₃ gave more of the above product, m. 256°; the evaporated solution after treatment with thiosulfate gave the IB, m. 164-5° (from absolute EtOH). Treatment of powd. I.HCl in PhCl at reflux with 20% excess BzCl gave 57.7% 2-(benzoyloxymethyl)benzimidazole (III) HCl salt (IIIA) and 14.5% of the more soluble 1-benzoyl-2-(benzoyloxymethyl)benzimidazole (IV). The former gave III, m. 146-7° (from dilute EtOH), which is stable in hot mineral acids (dilute) and in hot HCl forms the HCl salt, m. 233-5° (from EtOH or H₂O); heating with 4N H₂SO₄ gave the acid sulfate, C₁₅H₁₄O₆N₂S, m. 207-10° (from dilute H₂SO₄. Treatment with AgNO₃ as above gave the Ag salt, colorless solid of III. IV, m. 89-91°, is decomposed in hot mineral acids yielding salts of the III. The yellow oil observed in the above benzoylation treated with 4N HCl yields IIIA, with liberation of BzCl and BzOH; similar decomposition occurs on standing or heating to 80-100°; the oil contained 5.3% N. II with 20% excess BzCl in C₆H₆ gave after 1 hr. reflux 81-5% 1-methyl-2-(benzoyloxymethyl)benzimidazole-HCl, m. 195-7° (from dilute HCl), which on drying partly loses its HCl content; with NH₄OH this yields the free base, m. 144-6° (from H₂O). IA does not undergo the benzoylation reaction.

Zhurnal Obshchei Khimii 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 C26H41N5O7S, Quality Control of 7467-35-8.

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