Archives for Chemistry Experiments of 13395-16-9

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Bis-copper(II) Complex of Triply-linked Corrole Dimer and Its Dication

Copper complexes of corroles have recently been a subject of keen interest due to their ligand non-innocent character and unique redox properties. Here we investigated bis-copper complex of a triply-linked corrole dimer that serves as a pair of divalent metal ligands but can be reduced to a pair of trivalent metal ligands. Reaction of triply-linked corrole dimer 2 with Cu(acac)2 (acac=acetylacetonate) gave bis-copper(II) complex 2Cu as a highly planar molecule with a mean-plane deviation value of 0.020 A, where the two copper ions were revealed to be divalent by ESR, SQUID, and XPS methods. Oxidation of 2Cu with two equivalents of AgBF4 gave complex 3Cu, which was characterized as a bis-copper(II) complex of a dicationic triply-linked corrole dimer not as the corresponding bis-copper(III) complex. In accord with this assignment, the structural parameters around the copper ions were revealed to be quite similar for 2Cu and 3Cu. Importantly, the magnetic spin?spin interaction differs depending on the redox-state of the ligand, being weak ferromagnetic in 2Cu and antiferromagnetic in 3Cu.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Modifications of quinolones and fluoroquinolones: hybrid compounds and dual-action molecules

Abstract: This review is aimed to provide extensive survey of quinolones and fluoroquinolones for a variety of applications ranging from metal complexes and nanoparticle development to hybrid conjugates with therapeutic uses. The review covers the literature from the past 10?years with emphasis placed on new applications and mechanisms of pharmacological action of quinolone derivatives. The following are considered: metal complexes, nanoparticles and nanodrugs, polymers, proteins and peptides, NO donors and analogs, anionic compounds, siderophores, phosphonates, and prodrugs with enhanced lipophilicity, phototherapeutics, fluorescent compounds, triazoles, hybrid drugs, bis-quinolones, and other modifications. This review provides a comprehensive resource, summarizing a broad range of important quinolone applications with great utility as a resource concerning both chemical modifications and also novel hybrid bifunctional therapeutic agents. Graphical abstract: [Figure not available: see fulltext.].

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Aromatic Thiocyanation using Supported Copper(I) Thiocyanate

Charcoal Supported copper(I) thiocyanate can be used to convert bromo- and iodo-benzenes into phenyl thiocyanates with no contamination from phenyl isothiocyanates.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Transition metal complexes containing the S(NtBu)42- tetraimidosulfate dianion

Three novel metal complexes [(acac)2Cu2(NtBu)4S] (3), [Li(thf)4]2[I4Cd2(NtBu)4S] (4) and [(thf)2Li{(SiMe3)2N}Zn(NtBu)4S] (5) are prepared from the intended transmetalation of the dilithium complex of N,N?,N??,N???-tetrakis(tert-butyl)tetraimidosulfate [(thf)4Li2(NtBu)4S] (1). The two lithium cations are replaced by either the cationic (acac)Cu(ii) moiety, the neutral I2Cd(ii) residue or only a single lithium cation is substituted by the cationic (Me3Si)2NZn(ii) fragment. The complexes show two main results: first the S(NtBu)42- tetrahedron can serve as a ligand to transition metals from the soft Cu(ii) to the harder Zn(ii) at opposite sides and second the S-N bond distances vary only marginally in response to the various metals and the four distances constantly sum up to 6.38(2) A. Hence the electropositive sulfur atom responds by internal shift to the metal-polarized negative charge at the outside of the S(NR)42- tetrahedron. This journal is

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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UREA DERIVATIVES USEFUL AS CALCIUM RECEPTOR MODULATORS

The present invention provides compounds of formula (I): in which Y is oxygen or sulphur; R1 and R?1 are optionally substituted aryl, heteroaryl or a fused ring structure, R2and R’2 are each H, or optionally substituted alkyl, alkylaminoalkyl or dialkylaminoalkyl, or R2 and R’2 and their N form a saturated or unsaturated optionally substituted heterocycle, R3 represents a group of formula -(CH2)P-Ar-Rn, wherein p is 0 or 1 and, when p is 1, is optionally substituted, Ar is aryl or heteroaryl, and each R is H, halogen; hydroxyl; trifiuoromethyl; linear and branched alkyl, alkenyl, alkynyl, and alkoxyl groups, all optionally further substituted by one or more of hydroxy groups, halogen atoms, alkoxy groups, amino groups, and alkylthio groups; linear and branched alkoxyl groups; linear and branched thioalkyl groups; aryl groups; aralkyl groups; aralkoxy groups; aryloxy groups; perfluoroalkyl; -CN; -NR4R5, -C(=X)NR4R5,-O-C(=X)NR4R5, -SO2NR4R5, – Alk-NR4R5, -NZC(=X)(NH)qR6, -Alk-NZC(=X)(NH)qR6, -C(=X)R6, -Alk-C(=X)(NH)qR6, -NHSO2R7, -SO2R7, -SOR7, -SR7, or is a saturated or unsaturated heterocyclyl group, and salts and esters thereof, are useful in the treatment of conditions susceptible to modulating ion channels, to a process for their preparation, their application by way of medicaments, and to pharmaceutical compositions containing them.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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New copper(I) complexes bearing lomefloxacin motif: Spectroscopic properties, in vitro cytotoxicity and interactions with DNA and human serum albumin

In this paper we present lomefloxacin’s (HLm, 2nd generation fluoroquinolone antibiotic agent) organic and inorganic derivatives: aminomethyl(diphenyl)phosphine (PLm), its oxide as well as new copper(I) iodide or copper(I) thiocyanate complexes with PLm and 2,9-dimethyl-1,10-phenanthroline (dmp) or 2,2?-biquinoline (bq) as the auxiliary ligands. The synthesized compounds were fully characterised by NMR, UV?Vis and luminescence spectroscopies. Selected structures were analysed by theoretical DFT (density functional theory) methods. High stability of the complexes in aqueous solutions in the presence of atmosferic oxygen was proven. Cytotoxic activity of all compounds was tested towards three cancer cell lines (CT26 – mouse colon carcinoma, A549 – human lung adenocarcinoma, and MCF7 – human breast adenocarcinoma). All complexes are characterised by cytotoxic activity higher than the activity of the parent drug and its organic derivatives as well as cisplatin. Studied derivatives as well as parent drug do not intercalate to DNA, except Cu(I) complexes with bq ligand. All studied complexes caused single-stranded cleavage of the sugar?phosphate backbone of plasmid DNA. The addition of H2O2 caused distinct changes in the plasmid structure and led to single- and/or double-strain plasmid cleavage. Studied compounds interact with human serum albumin without affecting its secondary structure.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Architectural alterations from 1D to 3D coordination polymers based on a pair of isomeric linear and V-shaped triazole/thiophene/triazole bridging ligands

Four pairs of transition-metal [Co(II), Zn(II), Ni(II) and Cu(I)] coordination polymers have been prepared and characterized based on a pair of isomeric linear and V-shaped rigid thiophene-centered ditriazole bridging ligands [2,5-di(1H-1,2,4-triazol-1-yl)thiophene (L1) and 3,4-di(1H-1,2,4-triazol-1-yl)thiophene (L2)]. They are formulated as {[Co(L1)2(H2O)2](ClO4)2}n (1), {[Zn(L1)2(H2O)2](ClO4)2}n (2), {[Ni(L1)2(H2O)2](ClO4)2}n (3), {[Co(L2)2(H2O)2](ClO4)2}n (4), {[Zn(L2)2(H2O)2](ClO4)2}n (5), {[Ni(L2)2(H2O)2](ClO4)2}n (6), [Cu(L1)(CN)]n (7) and [Cu2(L2)(SCN)2]n (8), where distinct metal/ligand ratios (1:2, 1:1 and 2:1) and dimensions [one-dimensional (1D), two-dimensional (2D) and three-dimensional (3D)] have been observed because of the alterations of the coordination modes of central metal ions, the shape and conformation of ligands and the participancy of counterions. X-ray single-crystal diffraction analyses reveal that 1D chains have been formed in the cases of 4-6, while 2D planes have been built in 1-3. In contrast, 3D networks have been constructed in 7 and 8 with different topologies because of the further linkage of CN- and SCN- counterions.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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IR spectroscopy of two polymorphs of copper(I) thiocyanate and of complexes of copper(I) thiocyanate with thiourea and ethylenethiourea

Syntheses and infrared spectroscopic studies are reported for two different polymorphs of copper(I) thiocyanate and for adducts of copper(I) thiocyanate with thiourea (‘tu’) and ethylenethiourea (‘etu’ = imidazolidine-2-thione; (CH2NH)2CS)). These include the previously reported complex CuSCN/etu (1: 2), which has a trigonal monomeric structure, and CuSCN/etu (1: 1), which has a three-dimensional polymeric structure. A mechanochemical/infrared study of the CuSCN: tu (1: 2) system showed that no 1: 2 complex exists in this case, the product being a mixture of a 1: 3 complex and a novel 1: 0.5 complex. The latter complex was prepared both mechanochemically and from solution, and characterized by infrared and solid-state 65Cu broadline NMR spectroscopy. Diagnostic ligand and metal-ligand bands in the IR and far-IR spectra are assigned for both polymorphs of CuSCN and for all of the complexes studied and are discussed in relation to the structures of the complexes.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Synthesis, spectral and crystal structures of two new copper(I) complexes of di-2-pyridyl ketone (DPK) containing uncoordinated N-protonated ligand; [(DPK)H][CuX2] (X = I and NCS)

Two new copper(I) complexes of di-2-pyridyl ketone (DPK); [(DPK)H][CuI2] (1) and [(DPK)H][(Cu{NCS)2] (2) have been prepared and characterized by spectroscopic and crystallographic methods. Both complexes are colored and exhibit very broad and strong MLCT bands in the visible region. The IR spectra of these complexes are measured and discussed. The structure determination of complex 1 shows that it consists of discrete [(DPK)H]+ cation contains N-H¡¤¡¤¡¤N hydrogen bonds, and polymeric [CuI2]- anion. In the anion, each copper atom is in a distorted tetrahedral environment with Cu-I bond lengths from 2.570(4) to 3.072(4) A?. The structure of complex 2, which is similar to 1, features uncoordinated N-protonated di-2-pyridyl ketone cations and corrugated layers of [Cu(NCS)2](n), in which the copper atom is in a distorted tetrahedral CuS2N2 chromophore; Cu-N bond lengths are 1.954(2) and 1.958(2) A?, and Cu-S distances are 2.4120(8) and 2.4501(7) A?. (C) 2000 Elsevier Science Ltd.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Archives for Chemistry Experiments of Cuprous thiocyanate

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Alkali cation ligating chains and sheets of the macrocycle 1,7-dithia-18-crown-6 with bridging iodo- and thiocyanatocuprate(i) units

Treatment of an acetonitrile solution of CuI with 1,7-dithia-18-crown-6 (1,7-DT18C6) at 100C affords the coordination polymer ? 1[(CuI)2(1,7-DT18C6)2] (1) in which 1,7-DT18C6 ligands bridge (CuI)2 rings into double chains. 1D polymers of the type ?1[M{(Cu3I 4)(1,7-DT18C6)}] (M = K, 2; M = Cs, 3) can be isolated under similar conditions in the presence of respectively KI and CsI. Both contain bridging heptacyclic [Cu6I8]2- units but crystallise in different space groups, namely P1 and C2/m. The cesium cation of 3 is markedly displaced from the best plane through the thiacrown ether donor atoms. Reaction of 1,7-DT18C6 with CuSCN in the presence of NaSCN yields ?2[{Na(CH3CN)2} {(CuSCn) 2(1,7-DT18C6)}][Cu(SCN)2] (4), in which ?1[(CuSCN)2] double chains are linked through macrocycles into sheets. Infinite ? 1[{Cu(SCN)2}-] chains compensate the charge of the Na+ cations. Complex 1 can imbibe 0.90 mol CsNO3 per mol of 1,7-DT18C6 pairs.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”