Category: 4760-35-4

Martinez-Alanis, Paulina R. published the artcileCopper Versus Thioether-Centered Oxidation: Mechanistic Insights into the Non-Innocent Redox Behavior of Tripodal Benzimidazolylaminothioether Ligands, SDS of cas: 4760-35-4, the publication is Chemistry – A European Journal (2013), 19(19), 6067-6079, database is CAplus and MEDLINE.

A series of Cu⁺ complexes with ligands that feature varying numbers of benzimidazole/thioether donors and methylene or ethylene linkers between the central nitrogen atom and the thioether sulfur atoms have been spectroscopically and electrochem. characterized. Cyclic voltammetry measurements indicated that the highest Cu²⁺/Cu⁺ redox potentials correspond to sulfur-rich coordination environments, with values decreasing as the thioether donors are replaced by nitrogen-donating benzimidazoles. Both Cu²⁺ and Cu⁺ complexes were studied by DFT. Their electronic properties were determined by analyzing their frontier orbitals, relative energies, and the contributions to the orbitals involved in redox processes, which revealed that the HOMOs of the more sulfur-rich copper complexes, particularly those with methylene linkers (-N-CH₂-S-), show significant aromatic thioether character. Thus, the theor. predicted initial oxidation at the sulfur atom of the methylene-bridged ligands agrees with the exptl. determined oxidation waves in the voltammograms of the NS₃– and N₂S₂-type ligands as being ligand-based, as opposed to the copper-based processes of the ethylene-bridged Cu⁺ complexes. The electrochem. and theor. results are consistent with our previously reported mechanistic proposal for Cu²⁺-promoted oxidative C-S bond cleavage, which in this work resulted in the isolation and complete characterization (including by X-ray crystallog.) of the decomposition products of two ligands employed, further supporting the novel reactivity pathway invoked. The combined results raise the possibility that the reactions of copper-thioether complexes in chem. and biochem. systems occur with redox participation of the sulfur atom.

Chemistry – A European Journal 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, SDS of cas: 4760-35-4.

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

Rao, S. Srinivas published the artcileSynthesis of N,N¹-disubstituted bisbenzimidazole sulphides of potential pharmacological interest, Computed Properties of 4760-35-4, the publication is Journal of Chemical and Pharmaceutical Research (2014), 6(3), 1199-1204, 6 pp., database is CAplus.

A series of N,N¹-disubstituted bisbenzimidazole sulfides I (R = R¹ = H, Me, Et, Bn, n-Bu) were prepared by condensation followed by alkylation using DMF as solvent and K₂CO₃ as a base and tetra-n-butylammonium bromide (TBAB) as phase transfer catalyst.

Journal of Chemical and Pharmaceutical Research 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, Computed Properties of 4760-35-4.

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

Rao, S. Srinivas published the artcileSynthesis of 1-alkyl-2-chloromethylbenzimidazole under green conditions, SDS of cas: 4760-35-4, the publication is Asian Journal of Chemistry (2015), 27(1), 98-100, database is CAplus.

A green approach for the synthesis of 1-alkyl-2-chloromethylbenzimidazoles (alkyl = Me, Et, Bn) under, different conditions was developed from 2-chloromethylbenzimidazole by reaction with an alkylating agent (i.e. DMS, DES, PhCH₂Cl) by phys. grinding or by using green solvent like PEG-600 or by using microwave irradiation technique.

Asian Journal of 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, SDS of cas: 4760-35-4.

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

Monzani, Enrico published the artcileTyrosinase Models. Synthesis, Structure, Catechol Oxidase Activity, and Phenol Monooxygenase Activity of a Dinuclear Copper Complex Derived from a Triamino Pentabenzimidazole Ligand, Synthetic Route of 4760-35-4, the publication is Inorganic Chemistry (1998), 37(3), 553-562, database is CAplus and MEDLINE.

The dicopper(II) complex with the ligand N,N,N’,N’,N”-pentakis[(1-methyl-2-benzimidazolyl)methyl]dipropylenetriamine (I; LB5) was synthesized and structurally characterized. The small size and the quality of the single crystal required that data be collected using synchrotron radiation at 276 K. [Cu₂(LB5)(H₂O)₂][ClO₄]₄: platelet shaped, space group P1̅, a 11.028, b 17.915, c 20.745 Å, α 107.44, β 101.56, γ 104.89°, Z = 2; number of unique data, I ≥ 2σ(I) = 3447; number of refined parameters = 428; R = 0.12. The ligand binds the two coppers nonsym.; Cu1 is coordinated through five N donors and Cu2 through the remaining three N donors, while two H₂O mols. complete the coordination sphere. Cu1 has distorted TBP geometry, while Cu2 has distorted SP geometry. Voltammetric experiments show quasi-reversible reductions at the two Cu centers, with redox potential higher for the CuN₃ center (0.40 V) and lower for the CuN₅ center (0.17 V). The complex binds azide in the terminal mode at the CuN₃ center with affinity lower than that exhibited by related dinuclear polyaminobenzimidazole complexes where this ligand is bound in the bridging mode. The catechol oxidase activity of [Cu₂(LB5)]⁴⁺ was examined in comparison with that exhibited by [Cu₂(L-55)]⁴⁺ (L-55 = α,α’-bis{bis[(1-methyl-2-benzimidazolyl)methyl]amino}-m-xylene) and [Cu₂(L-66)]⁴⁺ (L-66 = α,α’-bis{bis[2-(1-methyl-2-benzimidazolyl)ethyl]amino}-m-xylene) by studying the catalytic oxidation of 3,5-di-tert-butylcatechol in MeOH/aqueous buffer pH 5.1. Kinetic experiments show that [Cu₂(L-55)]⁴⁺ is the most efficient catalyst (rate constant 140 M^-1 s^-1), followed by [Cu₂(LB5)]⁴⁺ (60 M^-1 s^-1), in this oxidation, while [Cu₂(L-66)]⁴⁺ undergoes an extremely fast stoichiometric phase followed by a slow and substrate-concentration-independent catalytic phase. The catalytic activity of [Cu₂(L-66)]⁴⁺, however, is strongly promoted by H₂O₂, because this oxidant allows a fast reoxidation of the dicopper(I) complex during turnover. The activity of [Cu₂(LB5)]⁴⁺ is also promoted by H₂O₂, while that of [Cu₂(L-55)]⁴⁺ is little affected. The phenol monooxygenase activity of [Cu₂(LB5)]²⁺ was compared with that of [Cu₂(L-55)]²⁺ and [Cu₂(L-66)]²⁺ by studying the ortho hydroxylation of Me 4-hydroxybenzoate to give Me 3,4-dihydroxybenzoate. The LB5 complex is much more selective than the other complexes since its reaction produces only catechol, while the main product obtained with the other complexes is an addition product containing a phenol residue condensed at ring position 2 of the catechol.

Inorganic 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, Synthetic Route of 4760-35-4.

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

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

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

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

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

Kilburn, John Paul published the artcileN-Methylanilide and N-methylbenzamide derivatives as phosphodiesterase 10A (PDE10A) inhibitors, Computed Properties of 4760-35-4, the publication is Bioorganic & Medicinal Chemistry (2013), 21(19), 6053-6062, database is CAplus and MEDLINE.

PDE10A is a recently identified phosphodiesterase with a quite remarkable localization since the protein is abundant only in brain tissue. Based on this unique localization, research has focused extensively on using PDE10A modulators as a novel therapeutic approach for dysfunction in the basal ganglia circuit including Parkinson’s disease, Huntington’s disease, schizophrenia, addiction and obsessive compulsive disorder. Medicinal chem. efforts identified the N-methyl-N-[4-(quinolin-2-ylmethoxy)-phenyl]-isonicotinamide (8) as a nanomolar PDE10A inhibitor. A subsequent Lead-optimization program identified analogous N-methylanilides and their corresponding N-methylbenzamides (29) as potent PDE10A inhibitors, concurrently some interesting and unexpected binding modes were identified.

Bioorganic & 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, Computed Properties of 4760-35-4.

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