Chiral Au(III) chelates exhibit unique NCI-60 cytotoxicity profiles and interactions with human serum albumin.

Au(III) bis(pyrrolide-imine) chelates are emerging as a class of versatile, efficacious metallodrug candidates. Here, we synthesised two enantiopure chiral ligands H2L1 and H2L2 (tetradentate cyclohexane-1,2-diamine-bridged bis(pyrrole-imine) derivatives). Metallation of the ligands with Au(III) afforded the chiral cationic complexes AuL1 and AuL2.

Precursor Engineering for the Synthesis of Mixed Anionic Metal (Cu, Mn) Chalcogenide Nanomaterials via Solvent-Less Synthesis.

Metal-organic ligands with mixed chalcogenides are potential compounds for the preparation of mixed anionic metal chalcogenide alloys. However, only a few of such ligands are known, and their complexes are not well explored. We have prepared homo- and hetero-dichalcogenoimidodiphosphinate [(EE'PPrNH)] (E, E' = Se, Se; S, S; S, Se) complexes of manganese and copper through metathetical reactions.

Self-assembled supramolecular structures of ,,' tridentate imidazole-phenol Schiff base compounds.

Three imidazole-derived Schiff base compounds comprising an -methyl imidazole group coupled to a phenol ring through an imine bond were synthesised. The structures differ by the substituent on the phenol ring at the 4-position: methyl (1), -butyl (2) and hydrogen (3). The compounds were synthesised using both a traditional reflux in solvent as well as an environmentally friendly solid-state reaction.

Insights into structural and physicochemical properties required for β-hematin inhibition of privileged triarylimidazoles.

In this study, we investigated a series of triarylimidazoles, in an effort to elucidate critical SAR information pertaining to their anti-plasmodial and β-hematin inhibitory activity. Our results showed that in addition to the positional effects of ring substitution, subtle changes to lipophilicity and imidazole ionisability were important factors in SAR interpretation. Finally, adsorption analysis indicated that these compounds exert their effect by inhibiting β-hematin crystal growth at the fast growing 001 face.

DNA interaction studies of rhenium compounds with Schiff base chelates encompassing biologically relevant moieties.

Herein, we report the DNA interaction studies of rhenium(I) and -(V) compounds with Schiff base chelates encompassing biologically relevant moieties. More specifically, the DNA interaction capabilities of these rhenium complexes were probed using Gel Electrophoresis and Calf Thymus-DNA titrations monitored by temperature-controlled electronic spectroscopy. The DNA binding modes of the metal compounds were corroborated by molecular docking simulations.

Evidence for Inhibition of Topoisomerase 1A by Gold(III) Macrocycles and Chelates Targeting Mycobacterium tuberculosis and Mycobacterium abscessus.

and the fast-growing species are two important human pathogens causing persistent pulmonary infections that are difficult to cure and require long treatment times. The emergence of drug-resistant strains and the high level of intrinsic resistance of call for novel drug scaffolds that effectively target both pathogens. In this study, we evaluated the activity of bis(pyrrolide-imine) gold(III) macrocycles and chelates, originally designed as DNA intercalators capable of targeting human topoisomerase types I and II (Topo1 and Topo2), against and We identified a total of 5 noncytotoxic compounds active against both mycobacterial pathogens under replicating conditions.

X-ray and DFT-calculated structures of bis[N-(quinolin-8-yl)benzamidato-κ(2)N,N']copper(II).

The application of transition metal chelates as chemotherapeutic agents has the advantage that they can be used as a scaffold around which ligands with DNA recognition elements can be anchored. The facile substitution of these components allows for the DNA recognition and binding properties of the metal chelates to be tuned. Copper is a particularly interesting choice for the development of novel metallodrugs as it is an endogenous metal and is therefore less toxic than other transition metals.

Ethylene oligomerization studies by nickel(ii) complexes chelated by (amino)pyridine ligands: experimental and density functional theory studies.

Reductions of imine compounds 2-methoxy-N-(1-(pyridin-2-yl)ethylidene)ethanamine (L1), 2-methoxy-N-((pyridin-2-yl)methylene)ethanamine (L2), N,N-diethyl-N-((pyridin-2-yl)methylene)ethane-1,2-diamine (L3) and 2-((pyridin-2-yl)methyleneamino)ethanol (L4) using NABH4 produced their corresponding amine analogues N-(2-methoxyethyl)-1-(pyridin-2-yl)ethanamine (L1a), 2-methoxy-N-((pyridin-2-yl)methyl)-ethanamine (L2a), N,N-diethyl-N-((pyridin-2-yl)methyl)ethane-1,2-diamine (L3a) and 2-((pyridin-2-yl)methylamino)ethanol (L4a) in good yields. Reactions of the (amino)pyridine ligands L1a–L4a with [NiBr2(DME)] afforded nickel(II) complexes, [NiBr2(L1a)2] (1), [NiBr2(L2a)2] (2), [NiBr2(L3a)2] (3) and [NiBr2(L4a)2] (4), respectively in quantitative yields. Molecular structures of complexes 2 and 4 confirmed the formation of the bis(chelated)nickel(II) complexes.

Packing forces in dichloridobis(3,5-diphenyl-1H-pyrazole-κN(2))cobalt(II) dichloromethane hemisolvate.

The title compound, [CoCl2(C15H12N2)2]·0.5CH2Cl2, was crystallized from a binary mixture of dichloromethane and hexane and a dimeric supramolecular structure was isolated. The Co(II) centre exhibits a distorted tetrahedral geometry, with two independent pyrazole-based ligands occupying two coordination sites and two chloride ligands occupying the third and fourth coordination sites.

Gold(III) macrocycles: nucleotide-specific unconventional catalytic inhibitors of human topoisomerase I.

Topoisomerase IB (Top1) is a key eukaryotic nuclear enzyme that regulates the topology of DNA during replication and gene transcription. Anticancer drugs that block Top1 are either well-characterized interfacial poisons or lesser-known catalytic inhibitor compounds. Here we describe a new class of cytotoxic redox-stable cationic Au(3+) macrocycles which, through hierarchical cluster analysis of cytotoxicity data for the lead compound, 3, were identified as either poisons or inhibitors of Top1.

Biodistribution (as determined by the radiolabelled equivalent) of a gold(III) bis(pyrrolide-imine) Schiff base complex: a potential chemotherapeutic.

The biodistribution of an N2 N2 ' tetradentate gold(III) chelate, which is known to be cytotoxic towards a range of human cancer cell lines, was determined by a radiolabelled equivalent of the compound. The (198) Au-labelled gold(III) chelate of a bis(pyrrolide-imine) Schiff base ligand with a three-carbon di(azomethine) linkage was successfully synthesised with a high radiochemical yield of 73% and radiochemical purity of >95%. The high energy γ-ray emitted by the (198) Au nucleus was used to follow the biodistribution of the compound in vivo in six male Sprague Dawley rats on a gamma camera.

(Pyridyl)benzoazole ruthenium(II) and ruthenium(III) complexes: role of heteroatom and ancillary phosphine ligand in the transfer hydrogenation of ketones.

The synthesis and structural characterization of ruthenium complexes supported by 2-(2-pyridyl)benzoazole ligands and their evaluation as catalysts in the transfer hydrogenation of ketones are reported. Reactions of 2-(2-pyridyl)benzoimidazole (L1), 2-(2-pyridyl)benzothiazole (L2) and 2-(2-pyridyl)benzoxazole (L3) with RuCl3·3H2O produced the corresponding complexes [RuCl3(L1)] (1), [RuCl3(L2)] (2) and [RuCl3(L3)] (3), respectively. Similarly, treatment of L1-L3 with RuCl2(PPh3)2 afforded the corresponding Ru(II) complexes [RuCl2(PPh3)2(L1)] (4), [RuCl2(PPh3)2(L2)] (5) and [RuCl2(PPh3)2(L3)] (6), respectively.

N-[(E)-Thio-phen-2-yl-methyl-idene]-1,3-benzothia-zol-2-amine.

In the title thio-phene-derived Schiff base compound, C(12)H(8)N(2)S(2), the thio-phene ring is slighty rotated from the benzothia-zole group mean plane, giving a dihedral angle of 12.87 (6)°. The largest displacement of an atom in the mol-ecule from the nine-atom mean plane defined by the non-H atoms of the benzothia-zole ring system is 0.

1,2-Bis[(2,2':6',2''-terpyridin-4'-yl)-oxy]ethane.

The title compound, C(32)H(24)N(6)O(2), has an inversion centre located at the mid-point of the central C-C bond of the diether bridging unit. The terminal pyridine rings are canted relative to the central pyridine ring, with dihedral angles of 12.98 (6) and 26.

6-Amino-1,3-dimethyl-5-[(E)-2-(methyl-sulfan-yl)benzyl-idene-amino]-pyrimidine-2,4(1H,3H)-dione-1,3,7,9-tetra-methyl-pyrimido[5,4-g]pteridine-2,4,6,8-tetrone (1/1).

In the title co-crystal, C(12)H(12)N(6)O(4)·C(14)H(16)N(4)O(2)S, both mol-ecules are essentially planar [maximum deviations = 0.129 (1) and 0.097 (1) Å, respectively].

1,6-Bis[(2,2':6',2''-terpyridin-4'-yl)-oxy]hexa-ne.

The mol-ecule of the title compound, C(36)H(32)N(6)O(2), lies about an inversion center, located at the mid-point of the central C-C bond of the diether bridge. The terminal pyridine rings form dihedral angles of 4.67 (7) and 26.

2-(3-Meth-oxy-phen-yl)-1,3-dihydro-1,3,2-benzodiaza-borole.

The title compound, C(13)H(13)BN(2)O, is one in a series of 1,3,2-benzodiaza-boroles featuring a 2-meth-oxy-phenyl substitution at the 2-position in the nitro-gen-boron heterocyle. The dihedral angle between the mean planes of the benzodiaza-borole and 2-meth-oxy-phenyl ring systems is 21.5 (1)°.

N,N-Bis(pyridin-2-ylmeth-yl)cyclo-hexa-namine.

The pyridine rings of the title compound, C(18)H(23)N(3), are in a nearly perpendicular orientation relative to the plane defined by the three amino-bonded C atoms, making dihedral angles of 87.4 (1) ° and 84.2 (1) °.

(E)-2,3-Bis[(E)-benzyl-idene-amino]-but-2-enedinitrile.

The asymmetric unit of the title compound, C(18)H(12)N(4), consists of a half-mol-ecule, where the two halves of the mol-ecule are related by inversion symmetry. The mol-ecule is effectively planar, with the largest deviation from the 22-atom mean plane, measuring 0.024 (2) Å, exhibited by the ortho-C atom of the phenyl ring.

1,4-Bis[(2,2':6',2''-terpyridin-4'-yl)-oxy]butane.

The title compound, C(34)H(28)N(6)O(2), has an inversion centre located at the mid-point of the central C-C bond of the diether bridging unit. The central pyridine rings of the terpyridyl units and the diether chain are co-planar: the maximum deviation from the 18-atom mean plane defined by the bridging unit and the central pyridyl ring is for the pyridyl N atom which sits 0.055 (1) Å above the plane.

1-(5,7-Dihy-droxy-2,2-dimethylchroman-6-yl)ethanone.

In the title mol-ecule, C(13)H(16)O(4), the pyran ring is in a half-chair conformation. There is an intra-molecular hydrogen bond involving the ketone O atom and an H atom of a phenol group which forms an S(6) ring. The ketone O atom is also involved in an inter-molecular hydrogen bond with a different phenolic H atom of a symmetry-related mol-ecule, forming C(6) chains along the c-axis direction.

2-Phenyl-naphtho-[1,8-de][1,3,2]diaza-borinane.

The title compound, C(16)H(13)BN(2), is one compound in a series of diaza-borinanes featuring substitution at the 1, 2 and 3 positions in the nitro-gen-boron heterocycle. The title compound is slightly distorted from planarity, with a dihedral angle of 9.0 (5)° between the mean planes of the naphthalene system and the benzene ring.

2-(4-Chloro-phen-yl)naphtho-[1,8-de][1,3,2]diaza-borinane.

The title compound, C(16)H(12)BClN(2), is one in a series of diaza-borinanes, derived from 1,8-diaminona-phthalene, featuring substitution at the 1, 2 and 3 positions in the nitro-gen-boron heterocycle. The structure deviates from planarity, the torsion angle subtended by the p-chloro-phenyl ring relative to the nitro-gen-boron heterocycle being -44-.3(3)°.

2-[4-(Methyl-sulfan-yl)phen-yl]naphtho[1,8-de][1,3,2]diaza-borinane.

The title compound, C(17)H(15)BN(2)S, is one member in a series of diaza-borinanes featuring substitution at the 1-, 2- and 3-positions in the nitro-gen-boron heterocycle. The dihedral angle between the mean planes of the naphthalene and phenyl ring systems is 19.86 (6)°.

A bis(amine-carboxylate) copper(II) coordination compound forms a two-dimensional metal-organic framework when crystallized from water and methanol.

When {2,2'-[(2-methyl-2-nitropropane-1,3-diyl)diimino]diacetato}copper(II), [Cu(C(8)H(13)N(3)O(6))], (I), was crystallized from a binary mixture of methanol and water, a monoclinic two-dimensional water- and methanol-solvated metal-organic framework (MOF) structure, distinctly different from the known orthorhombic one-dimensional coordination polymer of (I), was isolated, namely catena-poly[[copper(II)-mu(3)-2,2'-[(2-methyl-2-nitropropane-1,3-diyl)diimino]diacetato] methanol 0.45-solvate 0.55-hydrate], {[Cu(C(8)H(13)N(3)O(6))].