- Four-electron oxidative dehydrogenation induced by proton-coupled electron transfer in ruthenium(III) complex with 2-(1,4,5,6-tetrahydropyrimidin-2-yl) phenolate
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New ruthenium(II or III) complexes with general formula [Ru(O-N)(bpy) 2]n+ (O-N = unsymmetrical bidentate phenolate ligand; bpy = 2,2'-bipyridine) were synthesized, and their crystal structures and electrochemical properties were cha
- Mitsuhashi, Ryoji,Suzuki, Takayoshi,Sunatsuki, Yukinari
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- Identification of Adenosine Deaminase Inhibitors by Metal-binding Pharmacophore Screening
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Adenosine deaminase (ADA) is a human mononuclear Zn2+ metalloenzyme that converts adenosine to inosine. ADA is a validated drug target for cancer, but there has been little recent work on the development of new therapeutics against this enzyme. The lack of new advancements can be partially attributed to an absence of suitable assays for high-throughput screening (HTS) against ADA. To facilitate more rapid drug discovery efforts for this target, an in vitro assay was developed that utilizes the enzymatic conversion of a visibly emitting adenosine analogue to the corresponding fluorescent inosine analogue by ADA, which can be monitored via fluorescence intensity changes. Utilizing this assay, a library of ~350 small molecules containing metal-binding pharmacophores (MBPs) was screened in an HTS format to identify new inhibitor scaffolds against ADA. This approach yielded a new metal-binding scaffold with a Ki value of 26±1 μM.
- Adamek, Rebecca N.,Ludford, Paul,Duggan, Stephanie M.,Tor, Yitzhak,Cohen, Seth M.
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supporting information
p. 2151 - 2156
(2020/10/19)
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- Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion
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Imidazoline-fused [1,4]oxazepines (prepared in two simple steps from methyl 2-hydroxyaroates, ethylene diamine and bis-electrophilic aromatics) undergo a facile, good-yielding hydrolytic imidazoline ring expansion (HIRE) upon N-alkylation and treatment with aqueous K2CO3. The resulting arene-fused ten-membered lactams significantly add to the contemporary arsenal of small-molecule scaffolds where medium-sized ring systems are severely underrepresented.
- Sapegin, Alexander,Osipyan, Angelina,Krasavin, Mikhail
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supporting information
p. 2906 - 2909
(2017/04/11)
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- Atom-economical construction of tetracyclic [1,4]oxazepines involving intramolecular arylation of a 2-imidazoline moiety
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Novel [1,4]oxazepines containing a fused imidazoline moiety were synthesized from 2-hydroxyphenyl imidazolines and bis-electrophilic aromatic substrates in a reaction involving sequential nucleophilic aromatic substitution steps and a Smiles rearrangement. A notable step was the remarkably facile, metal-free intramolecular N-arylation of the imidazoline moiety with a fluoro-, nitro- or chloroaromatic or heteroaromatic ring. The approach presented in this Letter not only details access to a new, medicinally relevant tetracyclic [1,4]oxazepine core but also extends the scope of imidazoline arylation chemistry.
- Karamysheva, Kseniya,Reutskaya, Elena,Sapegin, Alexander,Dorogov, Mikhail,Krasavin, Mikhail
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supporting information
p. 5632 - 5636
(2015/09/22)
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- Effect of ortho-substituents on the stereochemistry of 2-(o-substituted phenyl)-1H-imidazoline-palladium complexes
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Palladium complexes composed of [Pd(Ln)2Cl2] (n = 1, 2, 3, 4, 6), [L5a]2[PdCl4] and [Pd(L5b)2], where L1 = 4,5-dihydro-2-phenyl-1H-imidazole (=2-phenyl-1H-imidazoline), L2 = 2-(o-fluorophenyl)-1H-imidazoline, L3 = 2-(o-methylphenyl)-1H-imidazoline, L4 = 2-(o-tert-butylphenyl)-1H-imidazoline, L5a = 2-(o-hydroxyphenyl)-1H- imidazolinium, L5b = 2-(1H-imidazolin-2-yl)phenolate, and L6 = 2-(o-methylphenyl)-1H-imidazole, were synthesized. Molecular structures of the isolated palladium complexes were characterized by single crystal X-ray diffraction analysis. The effect of ortho-substituents on the phenyl ring on trans-chlorine geometry was noted for complexes [Pd(L1)2Cl 2] 1a and 1b, [Pd(L2)2Cl2] 2 and [Pd(L6) 2Cl2] 6, whereas cis-chlorine geometry was observed for [Pd(L3)2Cl2] 3 and [Pd(L4)2Cl2] 4. PdCl2 reacts with 2-(o-hydroxyphenyl)-1H-imidazoline in DMF to give [L5a]+ and [L5b]- so that [L5a]2[PdCl 4] 5a and [Pd(L5b)2] 5b were obtained. In complex 5b, as an N,O-bidentate ligand, two ligands L5b coordinated with the central Pd(II) ion in the trans-form. The coordination of PdCl2 with 2-(o-hydroxyphenyl)-1H-imidazolines in solution was investigated by NMR spectroscopy. Palladium complexes composed of [Pd(Ln)2Cl2] (n = 1, 2, 3, 4, 6), [L5a]2[PdCl4] and [Pd(L5b)2], where L1 = 4,5-dihydro-2-phenyl-1H-imidazole (= 2-phenyl-1H-imidazoline), L2 = 2-(o-fluorophenyl)-1H-imidazoline, L3 = 2-(o-methylphenyl)-1H-imidazoline, L4 = 2-(o-tert-butylphenyl)-1H-imidazoline, L5a = 2-(o-hydroxyphenyl)-1H-imidazolinium, L5b = 2-(1H-imidazolin-2-yl) phenolate, and L6 = 2-(o-methylphenyl)-1H-imidazole, were synthesized and characterized by single crystal X-ray diffractometry.
- Gan, Zhibin,Kawamura, Kenjiro,Eda, Kazuo,Hayashi, Masahiko
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experimental part
p. 2022 - 2029
(2010/09/20)
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- Polymer-anchored oxovanadium(IV) complex for the oxidation of thioanisole, styrene and ethylbenzene
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The ligand 2-(2′-hydroxyphenyl)-1H-imidazoline (Hpimin) was covalently linked to chloromethylated polystyrene (PS-Cl). This resin was then allowed to react with vanadyl sulfate to afford the polymer-anchored oxovanadium(IV) complex, PS-[VO(pimin)x], which was characterised using elemental analysis, IR and AFM. This catalyst was shown to catalyse the hydrogen peroxide-based oxidation of styrene, ethylbenzene and thioanisole. A maximum conversion of ethylbenzene (30.6%) and styrene (99.9%) was obtained by using 0.025 g of PS-[VO(pimin)x] and 4 equiv. of hydrogen peroxide at 80 °C after 6 h. The oxidation of thioanisole proceeded quantitatively (99.6%) within 4 h, with 0.025 g of PS-[VO(pimin)x], at room temperature with 2 equiv. of hydrogen peroxide. At the steady state, the main products from the oxidation of the various substrates were benzaldehyde (57.6%) > 1-phenylethane-1,2-diol (16.2%) > benzoic acid (7.1%) > styrene oxide (3.1%) for styrene; acetophenone (20.5%) > benzaldehyde (2.7%) for ethylbenzene; and methyl phenyl sulfoxide (67.4%) > methyl phenyl sulfone (31.9%) for thioanisole.
- Tshentu, Zenixole R.,Togo, Chamunorwa,Walmsley, Ryan S.
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experimental part
p. 30 - 35
(2010/06/16)
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- Synthesis, characterization and anti-diabetic effect of bis[(1-R-imidazolinyl)phenolato]oxovanadium(IV) complexes
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The five-coordinate oxovanadium(IV) complexes; [VO(pimin)2] (1a), [VO(Etpimin)2] (2) and [VO(EtOHpimin)2] (3), were prepared by reacting the ligands; 2-(2′-hydroxyphenyl)-1H-imidazoline (piminH), 2-(2′-hydroxyphenyl)-1-eth
- Walmsley, Ryan S.,Tshentu, Zenixole R.,Fernandes, Manuel A.,Frost, Carminita L.
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experimental part
p. 2215 - 2221
(2011/01/11)
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- Study of synthesis of 2-(2-alkoxyphenyl)-1h-imidazoles. Comparison of oxidative aromatization reactions of imidazolines
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The reaction of methyl salicylate with ethane-1,2-diamine has been used to prepare 2-(2-hydroxyphenyl)-1H-imidazoline. This compound was alkylated with alkyl halides to give five new 2-(2-alkoxyphenyl)-1H-imidazolines (alkyl = propyl, isopropyl, isobutyl,
- Parik, Patrik,Senauerova, Sylva,Liskova, Vlasta,Handlir, Karel,Ludwig, Miroslav
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p. 835 - 841
(2007/10/03)
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- Zeolite-catalyzed simple synthesis of different heterocyclic rings, part 2
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A simple and environmentally friendly synthesis was developed for the preparation of 2-arylimidazoline derivatives and 2-arylbenzoxazole derivatives using a small pore size zeolite. The similar reaction was not applicable to the preparation of the sulfur-containing analogs cysteamine or 2-aminothiophenol, probably because of a disadvantageous reaction between the zeolite and the thio compound.
- Hegedues, Adrienn,Vigh, Ilona,Hell, Zoltan
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p. 428 - 431
(2007/10/03)
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- α1-Adrenoceptor agonists: The identification of novel α1A subtype selective 2′-heteroaryl-2-(phenoxymethyl)imidazolines
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Novel 2′-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human α1-adrenoceptors in vitro. The nature of the 2′-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. α1A Subtype selective agonists have been identified.
- Bishop, Michael J.,Barvian, Kevin A.,Berman, Judd,Bigham, Eric C.,Garrison, Deanna T.,Gobel, Michael J.,Hodson, Stephen J.,Irving, Paul E.,Liacos, James A.,Navas, Iii, Frank,Saussy Jr., David L.,Speake, Jason D.
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p. 471 - 475
(2007/10/03)
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- Reactions of 2-Hydroxybenzonitrile with Isocyanates
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Triethylamine catalyzes the reaction of 2-hydroxybenzonitrile (1) with arylisocyanates to form the corresponding carbamates 2a-c, as well as the cyclization of the latter compounds to either 4--3-aryl-2H-1,3-benzoxazin-2-ones 4a-c, or 4-arylamino-2H-1,3-benzoxazin-2-ones 7a-c, depending on the reaction temperature.Under analogous conditions, the carbamates obtained from 1 and 2-chloroethyl isocyanate, 3-chloropropyl isocyanate and ethyl isocyanatoacetate undergo a double cyclization yielding imidazo- and pyrimidobenzoxazinones 13a, b, 17.Upon heating in phenyl ether, compounds 7a-c, rearrange to 2-(2-hydroxyphenyl)-4(3H)-quinazolinones 10a-c.
- Petridou-Fischer, J.,Papadopoulos, E. P.
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p. 1159 - 1167
(2007/10/02)
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- Hydroformylation of olefins using azoxy-dentated ligands
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At a temperature in the range 100° C to 225° C the destructive dissociation of cobalt carbonyl compounds to cobalt metal and residue is inhibited by the action of one or more azoxy-dentated chelation ligands.
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