140-28-3Relevant articles and documents
Synthesis of heterobinuclear Cu(Ⅱ)-Ni(Ⅱ) complex: Structure, CT-DNA interaction, hydrolytic function and antibacterial studies
Ding, Peipei,Wang, Yang,Kou, Huizhi,Li, Jianfen,Shi, Baoxian
, p. 836 - 843 (2019)
A new benzyls pendant-armed macrobicyclic heterbinuclear Cu(Ⅱ)-Ni(Ⅱ) complex has been obtained by template-directed synthesis and characterized by elemental analysis, IR spectra, electrospray mass spectra, and single crystal X-ray diffraction. The complex was bridged by two phenolic oxygens and an acetate radical, with the Cu(Ⅱ)-Ni(Ⅱ) distance of 2.9292(8) ?. The hydrolytic function, CT-DNA binding and antibacterial properties were also studied. The initial rate values for the hydrolysis of 4-nitophenylphosphate to 4-nitrophenolate by the Cu(Ⅱ)-Ni(Ⅱ) complex was 1.33 × 10?5 s?1, and 104 times faster than that the spontaneous hydrolysis of the phosphate monoester. The complex shows a better binding property to CT-DNA and the intrinsic binding constant is 1.29 × 105 M?1. The Stern-Volmer constant is 1.25 × 105 M?1. The viscosity increased obviously with the increase of complex concentration, the results showed that the complex bind to DNA through intercalation mode, which was in accordance with the absorption and emission spectral studies. The antibacterial activities against E.coli was also investigated using the Gentamycinas reference system.
Brightly Luminescent and Kinetically Inert Lanthanide Bioprobes Based on Linear and Preorganized Chelators
Mohamadi, Ali,Miller, Lawrence W.
, p. 2540 - 2548 (2016)
The synthesis, photophysical properties, and kinetic stability of a series of water-soluble, highly emissive Tb(III) and Eu(III) complexes featuring triethylenetetraamine hexaacetic acid (TTHA) and cyclohexyl triethylenetetraamine hexaacetic acid (cyTTHA) chelator scaffolds and carbostyril sensitizers are reported. The unique and modular design of the chelators gives rise to striking quantum yields of emission in aqueous solutions (up to 54%) as well as the characteristic lanthanides' photophysical properties (long excited-state lifetimes, large effective Stokes shifts, and narrow emission peaks). Furthermore, the preorganized chelators (L3, L4, and L6) bind metal within minutes at ambient temperature yet exhibit substantial resistance to transchelation in the presence of a challenge solution (EDTA, 1 mM). Moreover, the Eu(III) complex of L4 remains stably luminescent in HeLa cells over hours, demonstrating the suitability of these compounds for live-cell imaging applications. Representative chelators suitable for derivatization and protein bioconjugation were also prepared that were functionalized with clickable azide and alkyne moieties, biotin, and trimethoprim (TMP). With exceptional long-wavelength brightness, enhanced kinetic inertness, and an adaptable synthetic route, the reported lanthanide complexes are promising probes and labels for time-gated bioanalysis, biosensing, and optical microscopy.
A combination risk assessment of paracetamol: Electrochemical oxidation behavior and cytotoxic effect evaluation of paracetamol in the presence of: N 1, N 2-dibenzylethane-1,2-diamine
Dowlati, Bahram,Othman, Mohamed Rozali,Ahmad, Azizan,Safaei, Elham
, p. 5121 - 5127 (2016)
The cytotoxic effect of paracetamol in the presence of a diamine derivative was evaluated in liver cells. In this study, hydropyrazinoquinoxalinylidene-acetamide (HPQA), as an agent that is toxic to the liver, was synthesized in an electrochemical cell as a simulated body environment by an electrooxidation reaction. A direct electron transfer (DET) mechanism occurred during the process on the surface of the carbon anode. The electrochemical oxidation of paracetamol was studied using cyclic voltammetry and controlled-potential coulometry (CPC) techniques. The product was characterized by FT-IR, 1H NMR, 13C NMR and ESI-MS2 after purification. The cytotoxicity of the final compound was evaluated using an MTT assay on the CCL-13 liver cell line. The results indicate that the presence of amine derivatives leads to an increase in the toxic effects of paracetamol in the human body. The cell viability at a concentration of 500 μg mL-1 was 78% for paracetamol, whereas the viability of liver cells in the presence of the product was 18% at 168 μg mL-1. A cycloaddition mechanism was suggested according to the overall results that were obtained.
Synthesis and antimycobacterial activity of ferrocenyl ethambutol analogues and ferrocenyl diamines
Razafimahefa, Dorothee,Ralambomanana, Dimby Andrianina,Hammouche, Lies,Pelinski, Lydie,Lauvagie, Sylvia,Bebear, Christiane,Brocard, Jacques,Maugein, Jeanne
, p. 2301 - 2303 (2005)
A new series of ferrocenyl diamino alcohols and diamines were synthesized and their inhibitory potencies were probed with Mycobacterium tuberculosis. Interestingly, ferrocenyl diamines 6a and b display significant activities against M. tuberculosis H37Rv.
Platinum Assisted Tandem P–C Bond Cleavage and P–N Bond Formation in Amide Functionalized Bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o: Synthesis, Mechanistic, and Catalytic Studies
Balakrishna, Maravanji S.,Kunchur, Harish S.
supporting information, (2022/01/19)
The reactions of amide functionalized bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o (1) with platinum salts are described. Treatment of 1 with [Pt(COD)Cl2] yielded a chelate complex, [PtCl2{o-Ph2PC6H4C(O)N(H)C6H4PPh2-o}κ2-P,P] (2), which on subsequent treatment with LiHMDS formed a novel 1,2-azaphospholene-phosphine complex [Pt(C6H5)Cl{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (3) involving a tandem P–C bond cleavage and P–N bond formation. The same complex 3 on passing dry HCl gas afforded the dichloro complex [PtCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (5). Complex 2 upon refluxing in toluene or treatment of 1 with [Pt(COD)Cl2] in the presence of a base at room temperature resulted in the pincer complex [PtCl{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (4). Reaction of 1 with [Pt(COD)ClMe] at room temperature also afforded the pincer complex [PtMe{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (6). Mechanistic studies on 1,2-azaphospholene formation showed the reductive elimination of LiCl to form a phosphonium salt that readily adds one of the P–C bonds oxidatively to the in situ generated Pt0 species to form a chelate complex 3. The analogous palladium complex [PdCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (7) showed excellent catalytic activity toward N-alkylation of amines with alcohols with a very low catalyst loading (0.05 mol %), and the methodology is very efficient toward the gram-scale synthesis of many N-alkylated amines.
Systematic research of H2dedpa derivatives as potent inhibitors of New Delhi Metallo-β-lactamase-1
Bai, Meng-Meng,Cui, De-Yun,Han, Jiang-Xue,Kong, Hong-Tao,Liu, Yi-Shuang,Shen, Bo-Yuan,Wang, Cong-Cong,Xiao, Chun-Ling,Yan, Da-Chao,Yang, Yi,Zhang, En
, (2020/06/01)
New Delhi Metallo-β-lactamase-1 (NDM-1), a Zn (II)-dependent enzyme, can catalyze the hydrolysis of almost all β-lactam antibiotics including carbapenems, resulting in bacterial antibiotic resistance, which threatens public health globally. Based on our finding that H2dedpa is as an efficient NDM-1 inhibitor, a series of H2dedpa derivatives was systematically prepared. These compounds exhibited significant activity against NDM-1, with IC50 values 0.06–0.94 μM. In vitro, compounds 6k and 6n could restore the activity of meropenem against Klebsiella pneumoniae, Escherichia coli and Proteus mirabilis possessing either NDM or IMP. In particular, the activity of meropenem against E. coli producing NDM-4 could be improved up to 5333 times when these two compounds were used. Time–kill cell-based assays showed that 99.9% of P. mirabilis were killed when treated with meropenem in combination with compound 6k or 6n. Furthermore, compounds 6k and 6n were nonhemolytic (HC50 > 1280 μg/mL) and showed low toxicity toward mammalian (HeLa) cells. Mechanistic studies indicated that compounds 6k and 6n inhibit NDM-1 by chelating the Zn2+ ion of the enzyme.
A new macrocyclic heterobinuclear Cu(II)-Zn(II) complex: synthesis, crystal structure, phosphate hydrolysis, and DNA binding studies
Kou, Huizhi,Wang, Yang,Ding, Peipei,Li, Jianfen,Shi, Baoxian
, p. 1683 - 1696 (2019/05/22)
A new macrocyclic heterobinuclear Cu(II)-Zn(II) complex was synthesized and characterized by elemental analysis, FT-IR, ES-MS, and single-crystal X-ray diffraction. Five-coordinate geometry for the new complex is proposed. The copper…zinc distance bridged by two phenolic oxygens and a acetate ligand is 2.9508 ?. The phosphate ester hydrolysis activity and the DNA binding ability of the complex were studied. The results showed that the present complex has an efficient catalytic activity of phosphoester bond cleavage. The catalytic rate constant kcat for the hydrolysis of 4-nitrophenyl phosphate disodium salt hexahydrate (pNPP) by the synthesized complex is 2.69 × 10?4 s?1 and 105 times faster than the spontaneous hydrolysis of the phosphate monoester. The complex shows a good binding ability to calf thymus (CT-DNA) and the corresponding binding constant is 1.9 × 105 M?1. The linear Stern-Volmer quenching constant obtained by the fluorescent spectroscopic is 6.3 × 104 M?1.
Manganese-Catalyzed Transfer Hydrogenation of Aldimines
Wei, Duo,Bruneau-Voisine, Antoine,Dubois, Maxime,Bastin, Stéphanie,Sortais, Jean-Baptiste
, p. 5256 - 5259 (2019/04/17)
The reduction of imines to amines via transfer hydrogenation was achieved promoted by phosphine-free manganese(I) catalyst. Using isopropanol as reductant, in the presence of tBuOK (4 mol %) and manganese complex [Mn(CO)3Br(κ2N,N-PyCH2NH2)] (2 mol %), a large variety of aldimines (30 examples) were typically reduced in 3 hours at 80 °C with good to excellent yield.
Design, synthesis and evaluation against Mycobacterium tuberculosis of azole piperazine derivatives as dicyclotyrosine (cYY) mimics
El-wahab, Hend A.A. Abd,Accietto, Mauro,Marino, Leonardo B.,McLean, Kirsty J.,Levy, Colin W.,Abdel-Rahman, Hamdy M.,El-Gendy, Mahmoud A.,Munro, Andrew W.,Aboraia, Ahmed S.,Simons, Claire
, p. 161 - 176 (2017/11/29)
Three series of azole piperazine derivatives that mimic dicyclotyrosine (cYY), the natural substrate of the essential Mycobacterium tuberculosis cytochrome P450 CYP121A1, were prepared and evaluated for binding affinity and inhibitory activity (MIC) against M. tuberculosis. Series A replaces one phenol group of cYY with a C3-imidazole moiety, series B includes a keto group on the hydrocarbon chain preceding the series A imidazole, whilst series C explores replacing the keto group of the piperidone ring of cYY with a CH2-imidazole or CH2-triazole moiety to enhance binding interaction with the heme of CYP121A1. The series displayed moderate to weak type II binding affinity for CYP121A1, with the exception of series B 10a, which displayed mixed type I binding. Of the three series, series C imidazole derivatives showed the best, although modest, inhibitory activity against M. tuberculosis (17d MIC = 12.5 μg/mL, 17a 50 μg/mL). Crystal structures were determined for CYP121A1 bound to series A compounds 6a and 6b that show the imidazole groups positioned directly above the haem iron with binding between the haem iron and imidazole nitrogen of both compounds at a distance of 2.2 ?. A model generated from a 1.5 ? crystal structure of CYP121A1 in complex with compound 10a showed different binding modes in agreement with the heterogeneous binding observed. Although the crystal structures of 6a and 6b would indicate binding with CYP121A1, the binding assays themselves did not allow confirmation of CYP121A1 as the target.
Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant
Wei, Duo,Bruneau-Voisine, Antoine,Valyaev, Dmitry A.,Lugan, No?l,Sortais, Jean-Baptiste
supporting information, p. 4302 - 4305 (2018/05/03)
A one-pot two-step procedure was developed for the alkylation of amines via reductive amination of aldehydes using molecular dihydrogen as a reductant in the presence of a manganese pyridinyl-phosphine complex as a pre-catalyst. After the initial condensation step, the reduction of imines formed in situ is performed under mild conditions (50-100 °C) with 2 mol% of catalyst and 5 mol% of tBuOK under 50 bar of hydrogen. Excellent yields (>90%) were obtained for a large combination of aldehydes and amines (40 examples), including aliphatic aldehydes and amino-alcohols.
