November 2022 - Imidazoles-derivatives

Musser, John H.’s team published research in Journal of Medicinal Chemistry in 30 | CAS: 4760-35-4

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, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

Musser, John H. published the artcilePhenylephrine derivatives as leukotriene D₄ antagonists, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is Journal of Medicinal Chemistry (1987), 30(11), 2087-93, database is CAplus and MEDLINE.

Two series of phenylephrine derivatives, e.g., I [R = H, Me; R¹ = CONEt₂, COEt, COPh, etc.; Z = (R)-CHOH, (±)-CHOH] and II (R² = 1-methyl-2-oxopyrrolidin-4-yl) (III) were prepared from phenylephrines. Thus, condensing (R)-3-HOC₆H₄CH(OH)CH₂NHMe.HCl with ClCONEt₂ gave (R)-3-HOC₆H₄CH(OH)CH₂NMeCONEt₂, which was alkylated with 2-(chloromethyl)quinoline to give I [R = Me, R¹ = CONEt₂, Z = (R)-CH(OH)] (IV). The most potent compound of the urea series, IV, was active orally as an inhibitor of leukotriene D₄ (LTD₄)- and ovalbumin-induced bronchospasm in the guinea pig, with ED₅₀ 56 mg/kg vs. LTD₄ and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD₄-induced contraction of isolated guinea pig tracheal strips, IV was a competitive inhibitor. In the 2nd series, III had oral ED₅₀ 36 mg/kg vs. LTD₄ and 95 mg/kg vs. ovalbumin. III selectively antagonized contractile responses of guinea pig trachea evoked by LTD₄. IV dilated the cat coronary artery and blocked the coronary constrictor effect of LTD₄, and also preserved myocardial integrity in rats 48 h after coronary-artery ligation. When tested in the rat alc.-induced gastric lesion model, III and IV manifested a dose-dependent mucosal protection against EtOH.

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

Currie, Kevin S.’s team published research in Journal of Medicinal Chemistry in 57 | CAS: 13682-33-2

Journal of Medicinal Chemistry published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, Quality Control of 13682-33-2.

Currie, Kevin S. published the artcileDiscovery of GS-9973, a Selective and Orally Efficacious Inhibitor of Spleen Tyrosine Kinase, Quality Control of 13682-33-2, the publication is Journal of Medicinal Chemistry (2014), 57(9), 3856-3873, database is CAplus and MEDLINE.

Spleen tyrosine kinase (Syk) is an attractive drug target in autoimmune, inflammatory, and oncol. disease indications. The most advanced Syk inhibitor, R406, (or its prodrug form fostamatinib), has shown efficacy in multiple therapeutic indications, but its clin. progress has been hampered by dose-limiting adverse effects that have been attributed, at least in part, to the off-target activities of R406. It is expected that a more selective Syk inhibitor would provide a greater therapeutic window. Herein the authors report the discovery and optimization of a novel series of imidazo[1,2-a]pyrazine Syk inhibitors. This work culminated in the identification of GS-9973, a highly selective and orally efficacious Syk inhibitor which is currently undergoing clin. evaluation for autoimmune and oncol. indications.

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

Piggott, Andrew M.’s team published research in Bioorganic & Medicinal Chemistry in 17 | CAS: 359860-27-8

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 C18H34N4O5S, Formula: C18H34N4O5S.

Piggott, Andrew M. published the artcileRapid isolation of novel FK506 binding proteins from multiple organisms using gDNA and cDNA T7 phage display, Formula: C18H34N4O5S, the publication is Bioorganic & Medicinal Chemistry (2009), 17(19), 6841-6850, database is CAplus and MEDLINE.

Reverse chem. proteomics using T7 phage display is a powerful technique for identifying cellular receptors of biol. active small mols. However, to date this method has generally been limited to cDNA libraries constructed from mRNA isolated from eukaryotes. In this paper, the authors describe the construction of the first prokaryotic T7 phage display libraries from randomly digested Pseudomonas stutzeri and Vibrio fischeri gDNA, as well as a plant cDNA library from Arabidopsis thaliana. The authors also describe the use of T7 phage display to identify novel proteins from environmental DNA samples using biotinylated FK506 as a model affinity probe.

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

Musser, John H.’s team published research in Journal of Medicinal Chemistry in 33 | CAS: 4760-35-4

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.

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

Sergievskii, A. V.’s team published research in Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) in 38 | CAS: 332026-86-5

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) published new progress about 332026-86-5. 332026-86-5 belongs to imidazoles-derivatives, auxiliary class Oxadiazole,Amine,Benzimidazole, name is 4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine, and the molecular formula is C7H8O3, Formula: C9H7N5O.

Sergievskii, A. V. published the artcile4-Aminofurazan-3-carboxylic Acid Iminoester in Reactions with N,O-Nucleophiles, Formula: C9H7N5O, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2002), 38(6), 872-874, database is CAplus.

Reactions of 4-aminofurazan-3-carboxylic acid iminoester with o-aminophenol and ethylenediamine give rise resp. to 4-(1,3-benzoxazol-2-yl)- and 1-(4,5-dihydro-1H-imidazol-2-yl)-1,2,5-oxadiazol-3-amines, with aminoethanol arises 2-[(Z)-1-amino-1-(4-amino-1,2,5-oxadiazol-3-yl)methylideneamino]-1-ethanol. Treating of 3-amino-4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazole with tri-Et orthoformate in acetic anhydride yielded benzo[4,5]imidazo[1,2-c][1,2,5]oxadiazolo[3,4-e]pyrimidine, and alkylation with haloalkanes furnished 3-amino-4-(1-R-benzo[d]imidazol-2-yl)-1,2,5-oxadiazoles.

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

Spiridonov, Kirill A.’s team published research in Mendeleev Communications in 31 | CAS: 258278-25-0

Mendeleev Communications 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 C13H9FO, Formula: C27H39ClN2.

Spiridonov, Kirill A. published the artcilePhosphite-containing iridium polarization transfer catalysts for NMR signal amplification by reversible exchange, Formula: C27H39ClN2, the publication is Mendeleev Communications (2021), 31(4), 475-477, database is CAplus.

Two new iridium complexes with an N-heterocyclic carbine and phosphite ligands have been synthesized and characterized. Bubbling of parahydrogen through their solutions resulted in the formation of several hydride complexes. In the presence of pyridine, this process is accompanied by transfer of spin order from the mol. hydrogen to pyridine mols. undergoing dynamic exchange between free and complex-bound states.

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

Marciniec, Barbara’s team published research in Journal of Thermal Analysis and Calorimetry in 88 | CAS: 2508-72-7

Journal of Thermal Analysis and Calorimetry 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, HPLC of Formula: 2508-72-7.

Marciniec, Barbara published the artcileThermal study of four irradiated imidazoline derivatives in solid state, HPLC of Formula: 2508-72-7, the publication is Journal of Thermal Analysis and Calorimetry (2007), 88(2), 337-342, database is CAplus.

Four imidazoline derivatives: antazoline (AN), naphazoline (NN), tymazoline (TM), xylometazoline (XM), in the form of hydrochlorides in solid phase have been subjected to high energy e-beam irradiation from an accelerator (≈10 MeV) at a dose varied from 25 to 200 kGy. The effects of the irradiation have been assessed by DSC, X-ray diffraction, FTIR, EPR and TLC. The standard sterilization dose of 25 kGy has been found to produce changes in the properties of one derivative (XM), two other ones (AN and TM) have been found sensitive to doses >100 kGy, whereas NN has been resistant to irradiation in the whole range studied (25-200 kGy). EPR results indicated that the changes taking place in the therapeutic substances studied are related to radical formation. The irradiation induced changes in color, a decrease or increase in the m.p., changes in the XRD pattern, small changes in the shape of FTIR peaks and the presence of radiolysis products. The XM compounds cannot be sterilized by irradiation because of the radiation induced changes in its physico-chem. properties.

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

Zakhari, N. Aziz’s team published research in Journal – Association of Official Analytical Chemists in 69 | CAS: 2508-72-7

Journal – Association of Official Analytical Chemists 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 C30H40N2O4, Application of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride.

Zakhari, N. Aziz published the artcileNonaqueous titration of halides of nitrogenous bases, using trifluoromethyl sulfonic acid, Application of N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, the publication is Journal – Association of Official Analytical Chemists (1986), 69(4), 620-4, database is CAplus.

CF₃SO₃H (I) [1493-13-6] in AcOH was compared with HClO₄ as a titrant in 4 solvent systems: AcOH, Ac₂O, a mixture of both, and Me₂CO. The comparison was limited to the determination of halides of nitrogenous bases with and without the use of Hg(AcO)₂ [1600-27-7]. The results for the visual titrations showed that both acids are comparable titrants. However, I was superior to HClO₄ in potentiometric titrations carried out in AcOH-Ac₂O mixtures Moreover, the nonoxidizing properties exhibited by I were advantageous over HClO₄ in the visual detection of end points in the titration of phenothiazine derivatives in anhydrous AcOH using crystal violet indicator.

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

Berezin, Andrey A.’s team published research in Organic & Biomolecular Chemistry in 12 | CAS: 2622-67-5

Organic & Biomolecular 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, Recommanded Product: 1,2-Diphenyl-1H-benzo[d]imidazole.

Berezin, Andrey A. published the artcileRing contraction of 1,3-diphenylbenzo[1,2,4]triazinyl radicals to 1,2-diphenylbenzimidazoles, Recommanded Product: 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is Organic & Biomolecular Chemistry (2014), 12(10), 1641-1648, database is CAplus and MEDLINE.

Reductive ring contraction of 1,3-diphenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yls (Blatter’s radicals) I (R = H, Cl, Br, I, CF₃, Ph, 2-furyl) using zinc powder (2 equivalent) in acetic acid heated to ca. 118 °C gives 1,2-diphenylbenzimidazoles II in high yield. 1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one and the zwitterionic tetraphenylhexaazaanthracene (TPHA) also undergo reductive ring contractions to give 1,2-diphenylbenzimidaz-6-ol and 1,2,6,7-tetraphenyl-1,7-dihydrobenzo[1,2-d:4,5-d’]diimidazole, resp. By using less zinc, the incomplete reduction of TPHA gave the stable organic radical 1,3,7,8-tetraphenyl-4,8-dihydro-1H-imidazo[4,5-g][1,2,4]benzotriazin-1-yl. Imidazolo-, oxazolo- and thiazolo-fused 1,2,4-benzotriazinyls all undergo zinc mediated ring contractions to give imidazolo-, oxazolo- and thiazolo-fused benzimidazoles in excellent yields.

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

Owen, John T. R.’s team published research in Journal – Association of Official Analytical Chemists in 64 | CAS: 2508-72-7

Owen, John T. R. published the artcileX-ray powder diffraction data for nine medicinal 2-imidazolines, Formula: C17H20ClN3, the publication is Journal – Association of Official Analytical Chemists (1981), 64(5), 1164-73, database is CAplus.

X-ray powder diffraction data for 9 2-imidazolines were obtained by the powder diffractometer and by the photog. Debye-Scherrer techniques. The data for individual 2-imidazolines are tabulated in terms of lattice spacings (d in Å) and the relative intensities of lines. The best method of packing for powder diffraction was investigated. It was advantageous to Cr Kα radiation in the Debye-Scherrer technique.

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