Month: December 2022

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

Weerakkody, Chandima published the artcileEnhanced Catalytic Properties of Molybdenum Promoted Mesoporous Cobalt Oxide: Structure-Surface-Dependent Activity for Selective Synthesis of 2-Substituted Benzimidazoles, Name: 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is ChemCatChem (2019), 11(1), 528-537, database is CAplus.

High-valent molybdenum ions were substituted into the cobalt oxide lattice through a one step, sol-gel method and investigated for selective synthesis of 2-substituted benzimidazoles. Catalyst synthesis involves surfactant assisted soft templating inverse micelle method, which forms mesopores by interconnected intraparticle voids. Substitutional doping of Mo⁶⁺ resulted in materials with modified structural, morphol., surface, and redox properties. The catalytic activity increased with Mo concentration until an optimum amount (3 % Mo incorporation). Modified material shows lattice expansion, increased surface oxygen vacancies, and high surface area, which are responsible for the higher catalytic activity in selective benzimidazole synthesis reaction. A strong correlation between surface properties of the catalyst and the product selectivity was observed and plausible mechanistic and kinetic data are proposed and collected, resp.

ChemCatChem 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 C5H6N2O2, Name: 1,2-Diphenyl-1H-benzo[d]imidazole.

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

Muller, Daniel S. published the artcileIn Situ Generation of Ru-Based Metathesis Catalyst. A Systematic Study, Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is ACS Catalysis (2019), 9(4), 3511-3518, database is CAplus.

A systematic study for the in situ generation of Ru-based metathesis catalysts was described. Assembly of com. available and inexpensive reagents [Ru(p-cymene)Cl₂]₂, SIPr·HCl, and n-BuLi led to the formation of 18 electron arene-ruthenium complexes that, in the presence of additives such as alkynes, cyclopropenes, and diazoesters, generated highly selective and efficient catalytic systems applicable to a variety of olefin metathesis transformations. Notably, we were able to achieve a productive TON of 4500 for the self-metathesis of Me oleate, a reaction which could be easily upscaled to 2 kg.

ACS 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, Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

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

Reddy, Vajrala Venkata published the artcileIdentification and synthesis of potential impurities of losartan potassium – a non-peptide angiotensinogen II receptor antagonist, COA of Formula: C8H13ClN2O, the publication is Asian Journal of Chemistry (2007), 19(5), 3789-3796, database is CAplus.

In the process for the preparation of losartan, identified four potential impurities ranging from 0.05-0.15 % were detected in HPLC. Based on the mass spectral data obtained by LC-MS anal. structure of these impurities were characterized as potassium salt of 2-n-butyl-5-chloro-4-hydroxymethyl-1-[(2′-(2H-tetrazole-5-yl)-1,1′-biphenyl-4-yl)methyl]-1H-imidazol (Imp-A, Isolosartan potassium), potassium salt of 5-(4′-methyl-1,1′-biphenyl-2yl)-2H-tetrazole (Imp-B, biphenyl tetrazole analog of 1), 2-butyl-4-chloro-1-2′-(1H-tetrazol-5-yl)-1,1′-biphenyl-4-ylmethyl-1H-imidazole-5-ethanoate (Imp-C, ester analog of losartan) and 2-n-butyl-4-chloro-1-2′-(1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl-5-triphenyl methoxy methyl-1H-imidazole (Imp-D, o-trityl losartan). These impurities were synthesized from an unambiguous route, confirmed the structure by collecting various spectral data and co-injected with losartan, retention time is matching with expected impurities. To our knowledge the impurities A-D were not reported as process impurities elsewhere.

Asian Journal of Chemistry published new progress about 79047-41-9. 79047-41-9 belongs to imidazoles-derivatives, auxiliary class Imidazole,Chloride,Alcohol, name is (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, and the molecular formula is C8H13ClN2O, COA of Formula: C8H13ClN2O.

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

Lin, Ho Shen published the artcileNonpeptide angiotensin II receptor antagonists: synthetic and computational chemistry of N-[[4-[2-(2H-tetrazol-5-yl)-1-cycloalken-1-yl]phenyl]methyl]imidazole derivatives and their in vitro activity, Synthetic Route of 79047-41-9, the publication is Journal of Medicinal Chemistry (1992), 35(14), 2658-67, database is CAplus and MEDLINE.

A series of nonpeptide angiotensin II receptor antagonists was synthesized and tested in vitro to investigate requirements for recognition by and binding to AT₁ receptors. Compared to a known series of N-(biphenylylmethyl)imidazoles, including losartan (DuP 753), which has a more rigid conformation in the 2′-tetrazolylbiphenyl moiety, the new series replaces the terminal Ph with cycloalkenyls. Compounds were made with five- to seven-membered rings and with either a hydroxymethyl or carboxyl group at the 5 position on the imidazole ring. The effects of the lipophilicity and steric bulk of the terminal ring system, the amount of π-electron d. in the terminal ring, and the relative spatial proximity of the tetrazolyl and the middle Ph are explored in terms of binding affinity to AT₁ receptors in rat adrenal glomerulosa and rabbit aorta. The physicochem. variables of the new compounds were quantitated by computational chem. and compared to those of losartan and its carboxyl metabolite. Potency at the AT₁ receptors is maximized when the terminal ring is six-membered; an aromatic ring binds better than a cycloalkenyl ring. The 5-carboxyimidazole compounds show higher affinity than the 5-hydroxymethyl series.

Journal of Medicinal Chemistry published new progress about 79047-41-9. 79047-41-9 belongs to imidazoles-derivatives, auxiliary class Imidazole,Chloride,Alcohol, name is (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, and the molecular formula is C8H13ClN2O, Synthetic Route of 79047-41-9.

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

Saha, Prasenjit published the artcileLigand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles, Safety of 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is Journal of Organic Chemistry (2009), 74(22), 8719-8725, database is CAplus and MEDLINE.

The synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles is described via intramol. cyclization of o-bromoaryl derivatives using copper(II) oxide nanoparticles in DMSO under air. E.g., cyclization of o-bromoaryl amidine I gave 95% benzimidazoles II. The procedure is exptl. simple, general, efficient, and free from addition of external chelating ligands. It is a heterogeneous process and the copper(II) oxide nanoparticles can be recovered and recycled without loss of activity.

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, Safety of 1,2-Diphenyl-1H-benzo[d]imidazole.

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

Mahale, Rajendra D. published the artcileDavis Oxaziridine-Mediated Asymmetric Synthesis of Proton Pump Inhibitors Using DBU Salt of Prochiral Sulfide, Synthetic Route of 161796-78-7, the publication is Organic Process Research & Development (2010), 14(5), 1264-1268, database is CAplus.

A simple and clean asym. synthesis of proton pump inhibitors using inexpensive 10-camphorsulfonyl oxaziridine is described. The activation of prochiral sulfide is based on use of the DBU salt which is capable of enhancing the reactivity and enantioselectivity.

Organic Process Research & Development published new progress about 161796-78-7. 161796-78-7 belongs to imidazoles-derivatives, auxiliary class Membrane Transporter/Ion Channel,Proton Pump, name is Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, and the molecular formula is C17H18N3NaO3S, Synthetic Route of 161796-78-7.

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

Kralova, Jana published the artcileThe effects of H₁-antihistamines on the nitric oxide production by RAW 264.7 cells with respect to their lipophilicity, SDS of cas: 2508-72-7, the publication is International Immunopharmacology (2009), 9(7-8), 990-995, database is CAplus and MEDLINE.

H₁-antihistamines are known to be important modulators of inflammatory response. However, the information about the influence of these drugs on reactive nitrogen species generation is still controversial. The main aim of the present study was to investigate the effects of selected H₁-antihistamines on nitric oxide production by lipopolysaccharide-stimulated murine macrophages RAW 264.7, measured as changes in inducible nitric oxide synthase (iNOS) protein expression in cell lysates by Western blotting and nitrite formation in cell supernatants using the Griess reaction. In pharmacol. non-toxic concentrations, H₁-antihistamines significantly inhibited nitrite accumulation that was not caused by the scavenging ability of drugs against nitric oxide, measured amperometrically. The degree of inhibition of nitrite accumulation pos. correlated with the degree of tested lipophilicity, measured by reversed-phase thin layer chromatog. Furthermore, H₁-antihistamines differentially modulated the iNOS protein expression. In conclusion, as was shown in this study, the modulation of nitric oxide production could be caused by the downregulation of iNOS protein expression and/or the iNOS protein activity.

International Immunopharmacology 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, SDS of cas: 2508-72-7.

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

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