20062-62-8Relevant articles and documents
Investigation of the mercury(II) coordination chemistry of tris[(1-methylimidazol-2-yl)methyl]amine by X-ray crystallography and NMR
Bebout, Deborah C.,Garland, Melissa M.,Murphy, Geoffrey S.,Bowers, Edith V.,Abelt, Christopher J.,Butcher, Raymond J.
, p. 2578 - 2584 (2003)
The coordination chemistry of Hg(II) with tris[(1-methylimidazol-2-yl)methyl]amine (TMIMA) was investigated. The structures of [Hg(TMIMA)2](ClO4)2 (1), [Hg(TMIMA)(NCCH3)](ClO4)2 (2) and [Hg(TMIMA)Cl]2(HgCl4) (3) were characterized by X-ray crystallography. Complex 1 has six strong Hg-Nimidazoyt bonds ranging from 2.257(5) to 2.631(6) A. Ligand geometry suggests the Hg-N(NR3) distances of 2.959(6) A in 1 reflects weak bonding interactions. This complex has a 199Hg chemical shift of -1496 ppm, significantly upfield from nitrogen coordination complexes with lower coordination numbers. The five-coordinate complex 2 has Hg-N(NR3), Hg-Nimidazoyl and Hg-Nacetonitrile bond lengths of 2.642(8), 2.198(5) and 2.264(11) A, respectively. Complex 3 is also five coordinate, with Hg-N(NR3), Hg-Cl and average Hg-N imidazoyl distances in the cations of 2.758(7), 2.424(2) and 2.29(4) A, respectively. Conditions for slow exchange on the J(HgH) coupling time-scale were found for both 1: 1 metal-to-ligand complexes in acetonitrile-d3. Observed heteronuclear coupling constants were similar to those associated with Hg(II) substituted proteins with histidine-metal bonds. Solution and solid-state comparisons to the Hg(II) coordination chemistry of tetradenate pyridyl ligands are made. Relevance to development of 199Hg NMR as a metallobioprobe is discussed. The Royal Society of Chemistry 2003.
Synthesis of 3-imidazolylazole derivatives from a new nitrile oxide [1]
Foti,Grassi,Risitano,La Rosa
, p. 539 - 540 (2001)
The synthesis of a series of 3-Imidazolylazole derivatives using cycloaddition reactions of a useful new nitrile oxide is described.
NOVEL TETRAHYDROPYRIDOPYRIMIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
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Page/Page column 20; 21, (2018/05/24)
The present invention provides novel compounds having the general formula: wherein R1, R2 and R3 are as described herein, compositions including the compounds and methods of using the compounds.
Synthesis and in-vitro reactivation screening of imidazolium aldoximes as reactivators of sarin and VX-inhibited human acetylcholinesterase (hAChE)
Sharma, Rahul,Gupta, Bhanushree,Sahu, Arvind Kumar,Acharya, Jyotiranjan,Satnami, Manmohan L.,Ghosh, Kallol K.
, p. 85 - 92 (2016/12/09)
Post-treatment of organophosphate (OP) poisoning involves the application of oxime reactivator as an antidote. Structurally different oximes are widely studied to examine their kinetic and mechanistic behavior against OP-inhibited cholinesterase enzyme. A series of structurally related 1,3-disubstituted-2-[(hydroxyiminomethyl)alkyl]imidazolium halides (5a–5e, 9a–9c) were synthesized and further evaluated for their in-vitro reactivation ability to reactivate sarin- and VX-inhibited human acetylcholinesterase (hAChE). The observed results were compared with the reactivation efficacy of standard reactivators; 2-PAM, obidoxime and HI-6. Amongst the synthesized oximes, 5a, 9a and 9b were found to be most potent reactivators against sarin-inhibited hAChE while in case of VX only 9a exhibited comparable reactivity with 2-PAM. Incorporation of pyridinium ring to the imidazole ring resulted in substantial increase in the reactivation strength of prepared reactivator. Physicochemical properties of synthesized reactivators have also been evaluated.
Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations
Primoi, Ines,Hrenar, Tomica,Baumann, Kreimir,Krito, Lucija,Krii, Ivana,Tomi, Srdlanka
, p. 153 - 160 (2015/02/19)
New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.
Cytotoxic effect of (1-methyl-1H-imidazol-2-yl)-methanamine and its derivatives in PtII complexes on human carcinoma cell lines: A comparative study with cisplatin
Ferri, Nicola,Cazzaniga, Stefano,Mazzarella, Luca,Curigliano, Giuseppe,Lucchini, Giorgio,Zerla, Daniele,Gandolfi, Raffaella,Facchetti, Giorgio,Pellizzoni, Michela,Rimoldi, Isabella
, p. 2379 - 2386 (2013/05/09)
The synthesis and pharmacological characterisation of (1-methyl-1H- imidazol-2-yl)-methanamine and its derivatives in PtII complexes are described. Six out of eleven new PtII complexes showed a significant cytotoxic effect on NCI-H460 lung cancer cell line with EC50 values between 1.1 and 0.115 mM, determined by MTT assay. Compound Pt-4a showed a particularly more potent cytotoxic effect than the previously described Pt II complex with 2,2′-bipyridine, [Pt(bpy)Cl2], with an EC50 value equal to 172.7 μM versus 726.5 μM respectively, and similar potency of cisplatin (EC50 = 78.3 μM) in NCI-H460 cell line. The determination of the intracellular and DNA-bound concentrations of 195Pt, as marker of the presence of the complexes, showed that the cytotoxic compound Pt-4a readily diffused into the cells to a similar extent of cisplatin and directly interacted with the nuclear DNA. Pt-4a induced both p53 and p21Waf expression in NCI-H460 cells similar to cisplatin. A direct comparison of the cytotoxic effect between compound Pt-4a and cisplatin on 12 different cancer cell lines demonstrated that compound Pt-4a was in general less potent than cisplatin, but it had a comparable cytotoxic effect on non-small-cell lung cancer NCI-H460 cells, and the colorectal cancer cells HCT-15 and HCT-116. Altogether, these results suggested that the PtII complex with 1-methyl-1H-imidazol-2-yl)-methanamine (compound Pt-4a), displayed a significant cytotoxic activity in cancer cells. Similarly to cisplatin this compound interacts with nuclear DNA and induces both p53 and p21waf, and thus it represents an interesting starting point for future optimisation of new PtII complexes forming DNA adducts.
The effect of neutral oximes on the reactivation of human acetylcholinesterase inhibited with paraoxon
Ribeiro, Tatiana S.,Prates, Arthur,Alves, Se?rgio R.,Oliveira-Silva, Jefferson J.,Riehl, Carlos A. S.,Figueroa-Villar, J. Daniel
experimental part, p. 1216 - 1225 (2012/10/18)
Important defense agents against chemical warfare weapons, which are reactivators of human acetylcholinesterase (huAChE) inhibited by neurotoxic organophosphorus compounds (OP), need a reasonable permeation of the hematoencephalic barrier (HB). In this wo
Synthesis and ocular effects of imidazole nitrolic acids
Oresmaa, Larisa,Kotikoski, Hanna,Haukka, Matti,Salminen, Johanna,Oksala, Olli,Pohjala, Esko,Moilanen, Eeva,Vapaatalo, Heikki,Vainiotalo, Pirjo,Aulaskari, Paula
, p. 4231 - 4236 (2007/10/03)
Novel 1-R-imidazole-2-nitrolic acids and 1-R-imidazole-5-nitrolic acids (R: H, Me, Bn) were synthesized from oximes by treatment with a mixture of fuming nitric acid and acetic acid. The effects of these potential nitric oxide-donating compounds were test
2-(1H-INDAZOL-6-YLAMINO)-BENZAMIDE COMPOUNDS AS PROTEIN KINASES INHIBITORS USEFUL FOR THE TREATMENT OF OPHTALMIC DISEASES
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Page 74, (2010/02/07)
Indazole compounds that modulate and/or inhibit the ophthalmic diseases and the activity of certain protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating tyrosine kinase signal transduction and thereby modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating ophthalmic diseases and cancer and other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma,rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.
Thiazole benzamide derivatives and pharmaceutical compositions for inhibiting cell proliferation, and methods for their use
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Page 31-32, (2010/02/03)
Aminothiazole compounds with mono-/di-substituted benzamide are represented by the Formula (I), and their pharmaceutically acceptable salts, pharmaceutically acceptable prodrugs, pharmaceutically active metabolites, and pharmaceutically acceptable salts of said metabolites are described. These agents modulate and/or inhibit the cell proliferation and activity of protein kinases and are useful as pharmaceuticals for treating malignancies and other disorders.
