Category: imidazoles-derivatives

Zubenko, A. A. published the artcileStudies of unsaturated azole derivatives. VIII. Novel syntheses of 2-ethynylbenzimidazoles, Formula: C9H9ClN2, the publication is Khimiya Geterotsiklicheskikh Soedinenii (1978), 1111-14, database is CAplus.

Ethynylbenzimidazole I (R = Me, R¹ = CCH) was obtained in 38-45% yields from I (R = CH:CH₂) by bromination, dehydrobromination to give 80% I (R¹ = CBr:CH₂), and further dehydrobromination, or in 25% yield by methylation of I (R = H, R¹ = CCH). Similarly, I (R = H, R¹ = CHO) treated with Ph₃:CBrCO₂Me gave 62% I (R¹ = CH:CBrCO₂Me), which was dehydrobrominated and decarboxylated to give 80% I (R = H, R¹ = CCH).

Khimiya Geterotsiklicheskikh Soedinenii 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 C6H12O2, Formula: C9H9ClN2.

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

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

Jeyachandran, Rajkumar published the artcileCopper-catalyzed CuAAC/intramolecular C-H arylation sequence: synthesis of annulated 1,2,3-triazoles, Application of 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is Beilstein Journal of Organic Chemistry (2012), 1771-1777, database is CAplus and MEDLINE.

Step-economical syntheses of annulated 1,2,3-triazoles, e.g., I, were accomplished through copper-catalyzed intramol. direct arylations in sustainable one-pot reactions. Thus, catalyzed cascade reactions involving [3 + 2]-azide-alkyne cycloadditions (CuAAC) and C-H bond functionalizations provided direct access to fully substituted 1,2,3-triazoles with excellent chemo- and regio-selectivities. Likewise, the optimized catalytic system proved applicable to the direct preparation of 1,2-diarylated azoles through a one-pot C-H/N-H arylation reaction.

Beilstein Journal of Organic 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, Application of 1,2-Diphenyl-1H-benzo[d]imidazole.

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

Dubey, P. K. published the artcileA facile solvent-free synthesis of 1-alkyl/aralkyl-2-(1-arylsulfonylalkyl) benzimidazoles using “TBAB” as surface catalyst, Safety of 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is Journal of Heterocyclic Chemistry (2010), 47(6), 1317-1322, database is CAplus.

Reaction of 2-(α-chloroalkyl)benzimidazoles with Na arylsulfinates (I) under solvent-free conditions in the presence of Bu₄NBr as surface catalyst, by simple phys. grinding using mortar and pestle, gave 2(1H)-[α-(arylsulfonyl)alkyl]benzimidazoles. Subsequent treatment with alkylating agents under solvent-free conditions resulted in 1-alkyl/aralkyl-2-[α-(arylsulfonyl)alkyl]benzimidazoles. Alternatively, the latter were also prepared directly from 1-alkyl/aralkyl-2-(α-chloroalkyl)benzimidazoles by reaction with I. All the reactions were free from organic solvents.

Journal of Heterocyclic 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, Safety of 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

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

Dubey, P. K. published the artcileSynthesis of 1-alkyl/aralkyl-2-[1-(arylsulfonyl)alkyl]benzimidazoles under phase-transfer catalysis (PTC) conditions, Related Products of imidazoles-derivatives, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2007), 46B(3), 488-491, database is CAplus.

Reaction of 2-(1-chloroalkyl)benzimidazoles (I) with Na arylsulfinates in CH₃CN under PTC conditions gives 2-[1-(arylsulfonyl)alkyl]benzimidazoles, alkylation of which by di-Me or di-Et sulfate or benzyl chloride gives the title compounds, e.g., II. These final products can also be prepared by reaction of Na arylsulfinates with 1-alkyl/aralkyl-2-(1-chloroalkyl)benzimidazoles (obtained by phase-transfer alkylation of I) in MeCN using benzyltriethylammonium chloride as phase-transfer catalyst.

Indian Journal of Chemistry, Section B: Organic Chemistry Including 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, Related Products of imidazoles-derivatives.

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

Ngambenjawong, Chayanon published the artcileMultivalent Polymers Displaying M2 Macrophage-Targeting Peptides Improve Target Binding Avidity and Serum Stability, Application In Synthesis of 359860-27-8, the publication is ACS Biomaterials Science & Engineering (2017), 3(9), 2050-2053, database is CAplus and MEDLINE.

Tumor-associated macrophages (TAMs) display a spectrum of phenotypes ranging from pro-tumoral/anti-inflammatory “M2-like” to antitumoral/pro-inflammatory “M1-like” subtypes and, consequently, high intratumoral M2-to-M1 ratios are typically indicative of poor disease prognosis. Cancer immunotherapies that selectively modulate M2-like TAMs, enabling reversal of the M2-to-M1 ratio, represent a promising anticancer intervention but are difficult to implement due to the lack of effective targeting systems. In this study, we report the development of high avidity, M2 macrophage-selective targeted drug delivery platforms based on M2 macrophage-targeting peptides (M2pep) grafted onto poly(N-(2-hydroxypropyl) methacrylamide). Furthermore, these M2pep-grafted polymers also exhibit improved serum stability along with M2 macrophage-selective toxicity.

ACS Biomaterials Science & Engineering 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, Application In Synthesis of 359860-27-8.

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

Zhang, Ruipu published the artcileOxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis, Computed Properties of 2622-67-5, the publication is Organic Letters (2017), 19(20), 5629-5632, database is CAplus and MEDLINE.

The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.

Organic Letters 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 C9H20Cl2Si, Computed Properties of 2622-67-5.

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

Zhang, Ling-chun published the artcileDetermination of antazoline hydrochloride in rat plasma by HPLC and its application to pharmacokinetic study, Application of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, the publication is Zhongguo Yiyuan Yaoxue Zazhi (2014), 34(17), 1456-1459, database is CAplus.

A HPLC method for the determination of antazoline hydrochloride in rat plasma was established and the pharmacokinetics of antazoline hydrochloride in rats were studied. A sensitive and specific HPLC method was developed and validated using phenacetin as the internal standard (IS). The analyte and the IS were extracted from rat by Et acetate under the basic condition. The analytes were separated by a C₁₈ column and detected with a variable wavelength UV-detector. The mobile phase consisted of methanol-5 mmol L^-1 tetra-Bu ammonium bromide (40:60) and the flow rate was 1.0ml·min^-1. Standard calibration graph for antazoline hydrochloride was linear over a curve range of 50-4 000 ng·ml^-1 (R=0.999 3) and the lower limit of quantification was 50 ng·ml^-1 using a plasma sample of 100 μl. The intra-and inter-day precision values were less than 13.3% relative standard deviation (RSD). The intra-day and inter-day assay precision was in the range of ±15% and the accuracy in the range of 89.9%-110.6%. The extraction recoveries were on the average of 80% for antazoline hydrochloride and 75%for IS. After i. g. administration of antazoline hydrochloride, the major pharmacokinetic parameters were as follows: AUC_0-t=(5.15±0.39) mg·h·L^-1, AUC_t-∞=(5.37±0.26) mg·h·L^-1, t_1/2=(3.91±0.88) h, CL=(1.86±0.09) L·kg^-1·h^-1, V=(8.07±2.51) L·kg^-1, C_max=(3.35±0.21) mg·L^-1, t_max=(0.75±0.36) h. This method was successfully applied to pharmacokinetic studies of antazoline hydrochloride after ig administration to SD rats.

Zhongguo Yiyuan Yaoxue Zazhi 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 C11H12O4, 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