Category: imidazoles-derivatives

Cauwenbergh, Thibault published the artcileContinuous Flow Synthesis of Sulfur- and Selenium-NHC Compounds (NHC=N-Heterocyclic Carbene), Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is European Journal of Organic Chemistry (2022), 2022(15), e202101296, database is CAplus.

The first continuous flow syntheses of sulfur- and selenium-NHC (NHC=N-heterocyclic carbene) adducts in unprecedented short reaction times and high yields are reported. The importance of these species in coordination chem. or as efficient tools for determining the π-acceptor character of NHC ligands make any improvement in their synthesis a worthy goal. Thiourea derivatives bearing both saturated and unsaturated NHCs were obtained using NEt3 as a weak base (homogeneous setup) in conjunction with a bed of elemental sulfur (S₈). The synthetic route proving optimal for selenoureas involves the use of a simple Se/K₂CO₃ heterogeneous microreactor design.

European Journal of Organic Chemistry 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, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

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

Albrecht, Markus published the artcileStructures and properties of complexes [MCl(C₅Me₅)(N-S)](PF₆), M = Rh, Ir, with N-S = 1-methyl-2-(alkylthiomethyl)-1H-benzimidazole ligands, Application of 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is Journal of Organometallic Chemistry (2000), 596(1-2), 84-89, database is CAplus.

The four complexes [MCl(C₅Me₅)(N-S)](PF₆), M = Rh, Ir; N-S = 1-methyl-2-(methylthiomethyl)-1H-benzimidazole (mmb) and 1-methyl-2-(tert-butylthiomethyl)-1H-benzimidazole (mtb) were synthesized and characterized by spectroscopy, electrochem. and x-ray crystallog. (as MeOH solvates). The essential coordination features, viz., longer M-S (∼2.38 A) and shorter M-N bonds (∼2.09 A) in five-membered chelate rings are common to all four species. Cyclic voltammetry reveals irreversible two-electron reduction to M^I complexes and partially reversible oxidation to Ir^IV species for [IrCl(C₅Me₅)(mtb)]⁺. The results are discussed in comparison with those obtained for α-diimine (N-N) complexes of the [MCl(C₅Me₅)]⁺ fragments.

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

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

El Alaoui, Abdessamad published the artcileShiga toxin-mediated retrograde delivery of a topoisomerase I inhibitor prodrug, Safety of N-(4-Hydroxyphenyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, the publication is Angewandte Chemie, International Edition (2007), 46(34), 6469-6472, database is CAplus and MEDLINE.

A retrograde strategy: An innovative cancer-cell delivery concept exploits the naturally evolved characteristics of the Shiga toxin B-subunit (STxB) for the intracellular activation of a newly synthesized prodrug at the level of the biosynthetic/secretory pathway. Retrograde prodrug targeting allows its slow release, which should sustain the presence of the active principle in dividing tumor cells.

Angewandte Chemie, International Edition published new progress about 901770-40-9. 901770-40-9 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Amide, name is N-(4-Hydroxyphenyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C16H21N3O3S, Safety of N-(4-Hydroxyphenyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide.

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

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

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

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

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

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

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