Category: imidazoles-derivatives

Yoshikawa, Masato published the artcileDesign and synthesis of potent and selective pyridazin-4(1H)-one-based PDE10A inhibitors interacting with Tyr683 in the PDE10A selectivity pocket, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Bioorganic & Medicinal Chemistry (2016), 24(16), 3447-3455, database is CAplus and MEDLINE.

Utilizing structure-based drug design techniques, we designed and synthesized phosphodiesterase 10A (PDE10A) inhibitors based on pyridazin-4(1H)-one. These compounds can interact with Tyr683 in the PDE10A selectivity pocket. Pyridazin-4(1H)-one derivative 1 was linked with a benzimidazole group through an alkyl spacer to interact with the OH of Tyr683 and fill the PDE10A selectivity pocket. After optimizing the linker length, we identified 1-(cyclopropylmethyl)-5-[3-(1-methyl-1H-benzimidazol-2-yl)propoxy]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (16f) as having highly potent PDE10A inhibitory activity (IC₅₀ = 0.76 nM) and perfect selectivity against other PDEs (>13,000-fold, IC₅₀ = >10,000 nM). The crystal structure of 16f bound to PDE10A revealed that the benzimidazole moiety was located deep within the PDE10A selectivity pocket and interacted with Tyr683. Addnl., a bidentate interaction existed between the 5-alkoxypyridazin-4(1H)-one moiety and the conserved Gln716 present in all PDEs.

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 C19H14N2, Application of (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

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

Pec, Pavel published the artcileInhibition of pig kidney diamine oxidase by some 4,5-dihydroimidazole derivatives, Synthetic Route of 2508-72-7, the publication is Acta Universitatis Palackianae Olomucensis, Facultas Rerum Naturalium (1988), 91(Chem. 27), 227-34, database is CAplus.

The inhibitory activity of some physiol. interesting 4,5-dihydroimidazole derivatives on the activity of diamine oxidase (EC 1.4.3.6) was investigated. The enzyme was isolated from the cortex of pig kidney. Using 2-Me, 2-benzyl, (tolazoline), 2-N(4-tolyl)-N-(3-hydroxyphenyl)aminomethyl (phentolamine), 2-(1-naphthyl)methyl (naphazoline), 2-(2,6-dimethyl-4-tert-butylphenyl)methyl (xylometazoline) and 2-(N-phenyl-N-benzylamino)methyl (antazoline) 4,5-dihydro-imidazoles, the enzyme inhibition was noncompetitive in all cases. The K_i values were in the range 0.2-1.5 mM. The relations among inhibitor structure, K_i, and possible physiol. effects were discussed.

Acta Universitatis Palackianae Olomucensis, Facultas Rerum Naturalium 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, Synthetic Route of 2508-72-7.

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

Huang, Jian-Qiang published the artcile[(NHC)Ni^IIH]-Catalyzed Cross-Hydroalkenylation of Cyclopropenes with Alkynes: Cyclopentadiene Synthesis by [(NHC)Ni^II]-Assisted C-C Rearrangement, Quality Control of 258278-25-0, the publication is Angewandte Chemie, International Edition (2019), 58(17), 5702-5706, database is CAplus and MEDLINE.

The cross-hydroalkenylation/rearrangement cascade (HARC), using a cyclopropene, e.g., 3′,4′-dihydrospiro[2-cyclopropene-1,1′(2’H)-naphthalene] and alkyne RCCR¹ (R = H, CH₃, C₂H₅, (CH₂)₂CH₃, OC₂H₅; R¹ = CH₂OCH₃, CH₂OC₆H₅, cyclohexyl, etc.) as substrate pairs was achieved for the first time by using new [(NHC)Ni(allyl)]BArF (Ar = mesityl, diisopropylphenyl, 3-pentyl) catalysts (NHCN-heterocyclic carbenes). By controlling the (NHC)Ni^IIH relative insertion reactivity with cyclopropene and alkyne, a broad scope of cyclopentadienes, e.g., I was obtained with high selectivity. The structural features of new (NHC)Ni^II catalyst were important for the success of the reaction. The mild reaction conditions employed may serve as an entry for exploring (NHC)Ni^II-assisted vinylcyclopropane rearrangement reactivity.

Angewandte Chemie, International Edition 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, Quality Control of 258278-25-0.

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

Miller, Ross A. published the artcileIodine as a Chemoselective Reoxidant of TEMPO: Application to the Oxidation of Alcohols to Aldehydes and Ketones, Safety of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, the publication is Organic Letters (2003), 5(3), 285-287, database is CAplus and MEDLINE.

Chemoselective alc. oxidations using catalytic TEMPO and stoichiometric iodine as the terminal oxidant were studied. Iodine was compared to other pos. halogens as the terminal oxidant and shown to be superior in cases of electron-rich and heteroaromatic rings. The new conditions were successfully applied to the oxidation of 2-butyl-5-chloro-4-imidazolemethanol to its aldehyde derivative, which is an important intermediate in the synthesis of losartan.

Organic Letters 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, Safety of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol.

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

Jeong, Seung Pyo published the artcilePolymeric Functionalization of Cyclic Olefin Copolymer Surfaces with Nonbiofouling Poly(oligo(Ethylene Glycol) Methacrylate), Application In Synthesis of 359860-27-8, the publication is Asian Journal of Organic Chemistry (2013), 2(7), 568-571, database is CAplus.

A photoreaction-based method was developed for forming functionalizable and nonbiofouling Poly(oligo(Ethylene Glycol) Methacrylate) (pOEGMA) films on chem. inert Cyclic olefin copolymer (COC) surfaces, and generated a protein pattern on COC by using the post-functionalizability of pOEGMA. The method used herein will not only widen the applications of COC substrates to multiplexed detection of analytes in microfluidic devices and biosensors, but also be applicable to various other polymeric materials that need to be functionalized spatioselectively for their applications. In that sense, the photoreaction-based functionalization developed in this work is advantageous because it could be seamlessly combined with conventional lithog. techniques.

Asian Journal of Organic Chemistry 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

Molderings, G. J. published the artcileInhibitory presynaptic imidazoline receptors on sympathetic nerves in the rabbit aorta differ from I₁– and I₂-imidazoline binding sites, Quality Control of 2508-72-7, the publication is Naunyn-Schmiedeberg’s Archives of Pharmacology (1995), 351(5), 507-16, database is CAplus and MEDLINE.

The involvement of imidazoline receptors in modulation of noradrenaline release was investigated in the rabbit aorta preincubated with [³H]noradrenaline and superfused with physiol. salt solution containing cocaine, corticosterone and propranolol. After blockade of α₂-autoreceptors by rauwolscine, the elec. evoked tritium overflow was inhibited by various imidazolines and guanidines. The rank order of potency was BDF 7579 (4-chloro-2-isoindolinylguanidine) ≥ BDF 6143 (4-chloro-2-(2-imidazolin-2-ylamino)-isoindoline) > BDF 6100 [2-(2-imidazolin-2-ylamino)-isoindoline] > clonidine > ST587 (2-(2-chloro-5-trifluoromethylphenylimino)imidazolidine nitrate) ≥ cirazoline > tolazoline > idazoxan > phentolamine. Comparison of the potencies of these drugs with those previously found for the presynaptic imidazoline receptors in the rabbit pulmonary artery revealed a very good correlation. In contrast, no pos. correlation was found with their affinities for the I₁– and I₂-imidazoline binding sites in bovine adrenal medullary membranes and with their lipophilicity (log P values). The elec. evoked tritium overflow was also inhibited by the recently identified endogenous imidazoline receptor ligand agmatine, but was not affected by amiloride. In further series of experiments, the ability of putative antagonist at presynaptic imidazoline receptors to counteract the inhibitory effect of imidazoline derivatives was determined Amiloride, imidazole-4-acetic acid and 1-benzylimidazole did not attenuate the inhibitory effect of BDF 6143 on the elec. evoked tritium overflow. In contrast, rauwolscine antagonized the inhibitory effect of various imidazolines; rauwolscine was clearly less potent in antagonizing the effect of clonidine, BDF 6143 and cirazoline (apparent pA₂ 6.48-7.32) than in antagonizing that of oxymetazoline and moxonidine (apparent pA₂ 8.33 and 8.12, resp.). In a final series of experiments, BDF 6143 (under the conditions applied a selective agonist at presynaptic imidazoline receptors) proved to be considerably less potent in inhibiting tritium overflow evoked by high K⁺ than by elec. stimulation, whereas moxonidine (in rabbit aorta a selective agonist at presynaptic α₂-adrenoceptors) exhibited similar potency in inhibiting the overflow evoked by both methods of stimulation. It is concluded that noradrenaline release in the rabbit aorta is inhibited via both α₂-autoreceptors and presynaptic imidazoline receptors which can be activated by the endogenous imidazoline receptor ligand agmatine. The occurrence of such an α₂-adrenoceptor-independent mechanism is compatible with the ability of K⁺ ions to attenuate the inhibitory effect of an imidazoline receptor agonist but not of an α₂-adrenoceptor agonist, since susceptibility to K⁺ ions has been suggested to be a typical feature of imidazoline recognition sites. The presynaptic imidazoline receptor in rabbit aorta appears to be identical with the previously characterized presynaptic imidazoline receptor in rabbit pulmonary artery, but differs clearly from the I₁ and I₂ binding sites in the bovine adrenal medulla.

Naunyn-Schmiedeberg’s Archives of Pharmacology 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, Quality Control of 2508-72-7.

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

Miralles, Nuria published the artcileCopper-Mediated S_N2′ Allyl-Alkyl and Allyl-Boryl Couplings of Vinyl Cyclic Carbonates, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Organic Letters (2017), 19(22), 6096-6099, database is CAplus and MEDLINE.

A method for the Cu-catalyzed borylmethylation and borylation of vinyl cyclic carbonates through an S_N2′ mechanism is reported. These singular reactions involve selective S_N2′ allylic substitutions with concomitant ring opening of the cyclic carbonate and with extrusion of CO₂ and formation of a useful hydroxyl functionality in a single step. The stereoselectivity of the homoallylic borylation and allylic borylation processes can be controlled, and synthetically useful unsaturated (E)-pent-2-ene-1,5-diols and (E)-but-2-ene-1,4-diols are accessed.

Organic Letters 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

Peng, Xiao-Chong published the artcileActivated carbon supported hafnium(IV) chloride as an efficient, recyclable, and facile removable catalyst for expeditious parallel synthesis of benzimidazoles, Application of 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is Catalysts (2020), 10(4), 436, database is CAplus.

A highly efficient method for parallel synthesis of a diversity of 1,2-disubstituted benzimidazoles from N-substituted phenylenediamines and aldehydes has been developed by using 10 mol% HfCl₄ on activated carbon (HfCl₄/C) as the catalyst. The newly reported HfCl₄/C catalyst not only mediated fast and clean formation of benzimidazoles but also could be easily removed from the reaction solution and reused up to eight times. Scanning electron microscope (SEM) and thermal desorption studies showed that activated carbon could reversibly adsorb and release Hf(IV) in ethanol upon cooling and heating, thereby serving as a thermal-controlled solid support.

Catalysts 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

Tomlin, Frederick M. published the artcileSite-specific incorporation of quadricyclane into a protein and photocleavage of the quadricyclane ligation adduct, Category: imidazoles-derivatives, the publication is Bioorganic & Medicinal Chemistry (2018), 26(19), 5280-5290, database is CAplus and MEDLINE.

The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative Here we show that a QC amino acid can be incorporated into a protein site-specifically using the pyrrolysine-based genetic code expansion platform, and subsequently used for ligation chem. Addnl., we exploited the photolability of the QC ligation product to render the adduct cleavable with a handheld UV lamp. We further developed a protein purification method that involves QC ligation of biotin to a protein of interest, capture on streptavidin resin, and finally release using only UV light. The QC ligation thus brings novel chem. manipulations to the realm of bioorthogonal chem.

Bioorganic & Medicinal Chemistry 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 C11H15BFNO3, Category: imidazoles-derivatives.

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

Rooney, E. K. published the artcileInteraction of antihistamines with lipid bilayers, Safety of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, the publication is Biochemical Pharmacology (1979), 28(14), 2199-205, database is CAplus and MEDLINE.

All the 10 H₁-antagonists tested reduced the phase transition temperature of a dipalmitoyl phosphatidylcholine lipid bilayer. The binding constants for the drug to the lipid were calculated The H₂-antagonists, cimetidine (I) [51481-61-9] and metiamide [34839-70-8] had no effect on the lipid phase transition temperatures

Biochemical Pharmacology 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, Safety of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride.

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