Synthesis and crystal structures of cobalt(III), copper(II), nickel(II) and zinc(II) complexes derived from 4-methoxy-N′-(pyridin-2-ylmethylene)benzohydrazide with urease inhibitory activity

Abstract

Urease catalyzes the decomposition of urea into ammonia, which has harmful effects on both human health and fertile soil. Aiming at exploring novel urease inhibitors, a series of hydrazone compounds and their Co^III, Cu^II, Ni^II, and Zn^II complexes were prepared from 4-methoxy-N'-(pyridin-2-ylmethylene)benzohydrazide (HL). They are [CoClL(NCS)] (1), [CoL₂]·Cl·CH₃OH·H₂O (2), [CuL(NCNCN)]_n·nCH₃OH (3), [NiL(HL)]·ClO₄·CH₃OH (4) and [ZnClL(OH₂)]·CH₃OH (5). The compounds were characterized by physico-chemical methods. Structures of the complexes were further confirmed by single crystal X-ray diffraction. The metal ions in 1, 3, and 5 display square pyramidal coordination and 2 and 4 display octahedral coordination. The inhibitory effects of the compounds on Jack bean urease were evaluated. The results showed that 3 has effective urease inhibitory activity, with IC₅₀ value of (7.3?±?1.0) μmol L^?1.     

Syntheses,crystal structures,and Jack bean urease inhibitory activities of copper(II) complexes derived from 4-tert-butyl-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide

Two new copper(II) complexes, [CuL(HL)]·ClO₄ (1) and [Cu₂Br₂L₂]·0.85H₂O (2), where L is the monoanionic form of 4-tert-butyl-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide (HL), have been prepared. The complexes were characterized by infrared and UV–vis spectra, and single crystal X-ray diffraction. Complex 1 is a mononuclear copper(II) species and 2 is a bromido-bridged dinuclear copper(II) species. The Cu ion in 1 is in an octahedral coordination mode and that in 2 is trigonal-bipyramidal. The Jack bean urease inhibitory assay indicated that 2 is active, with IC₅₀ value of 20.6 ± 2.3 μmol L^?1, while 1 is inactive. Molecular docking of 2 with Jack bean urease was studied.     

Synthesis and crystal structures of three new complexes derived from 3-(pyridin-3′-yl)-5-(pyridin-2′′-yl)-1,2,4-triazole

Three new coordination complexes, [Cd₂(ppt)₂(cpba)]?·?(H₂O)₂ (1), [Zn(ppt)₂]?·?(H₂O) (2), and [Zn(MoO₄)(Hppt)] (3) (H₂cpba: 3-(2′-carboxy-phenoxy)-benzoic acid; Hppt: 3-(pyridin-3′-yl)-5-(pyridin-2′′-yl)-1,2,4-triazole), were synthesized under hydrothermal conditions. Their structures have been determined by single crystal X-ray diffraction analyses and further characterized by elemental analyses, IR spectra, and thermogravimetric analyses. X-ray diffraction analyses revealed that Cd(II) ions are linked by ppt^? to form a ladder-shaped structure along the a-axis and further displays a 2-D supramolecular architecture with cpba^2? along the c-axis. In 2, each Zn(ppt)₂ fragment is linked by the nitrogen of pyridin-3′-yl from the neighboring Zn(ppt)₂ forming a V-shaped chain. Compound 3 consists of a ladder structure, in which each {MoO₄} unit is a bridge linking three Zn(Hppt)²⁺ fragments.     

Synthesis,characterization and crystal structures of copper(II), zinc(II) and vanadium(V) complexes,derived from 3-methyl-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide,with antibacterial activity

Three copper(II), zinc(II), and vanadium(V) complexes, [CuL(HL)]ClO₄ (1), [ZnL₂] (2) and [VO₂L] (3), where L is the anionic form of 3-methyl-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide (HL), were prepared and characterized by IR, UV–vis and single-crystal X-ray determination. X-ray analysis indicates that the complexes are mononuclear species, with the Cu and Zn ions in 1 and 2 in octahedral coordination, and with the V ion in 3 in trigonal bipyramidal coordination. The hydrazone compound and the three complexes were evaluated for antibacterial activities. The copper complex has effective activities.     

Synthesis and crystal structures of two zinc(II) complexes derived from N-isopropyl-N′-[1-(2-methoxyphenyl)methylidene]ethane-1,2-diamine

Two isostructural mononuclear zinc(II) complexes, [ZnLBr₂] (I) and [ZnLI₂] (II), derived from the Schiff base N-isopropyl-N′-[1-(2-methoxyphenyl)methylidene]ethane-1,2-diamine (L), have been synthesized and characterized by elemental analysis, IR spectra, and X-ray single-crystal diffraction. The crystal of I is monoclinic: space group P2₁/n, a = 14.476(1) Å, b = 7.327(1) Å, c = 17.528(1) Å, β = 101.153(1)°, V = 1824.0(3) ų, Z = 4. The crystal of II is monoclinic: space group P2₁/n, a = 14.482(1), b = 7.329(1), c = 17.528(1)Å, β = 101.195(2)°, V = 1825.0(3)ų, Z = 4. The Zn atom in each complex is four-coordinated in a tetrahedral coordination, with one imine N and one amine N atoms of L, and two halide atoms. Both complexes and the Schiff base were tested in vitro for their antibacterial activities.     

Synthesis and crystal structure of a novel tri-nuclear nickel(II) complex derived from N,N′-(2-hydroxypropane-1,3-diyl)bis(salicylaldimine)

A novel tri-nuclear nickel(II) complex, [Ni₃L₂(μ₂-η¹:η¹-OAc)₂(μ₁-η¹:η⁰-OAc)₂] · H₂O (H₂L is N,N′-(2-hydroxypropane-1,3-diyl)-bis(salicylaldimine), was prepared. The complex was characterized by elemental analysis, IR spectra, and single crystal X-ray determination (CIF file CCDC no. 993163). Crystal of the complex crystallizes in the monoclinic space group P2₁/n. The unit cell parameters: a = 12.5602(9), b = 13.2104(10), c = 15.0329(10) Å, β = 113.194(2)°, V = 2292.7(3) ų, Z = 2, R ₁ = 0.0506, wR ₂ = 0.1342, S = 1.067. The complex possesses crystallographic inversion center symmetry. The Ni atoms are in octahedral coordination spheres. The Ni?Ni distances are 3.022(1) Å.     

Synthesis and X-ray crystal structures of N,N,N′,N′-tetraalkylpyridine-2,6-dithiocarboxamides (S-dapt) complexes of cobalt(II) and nickel(II)

Reactions of anhydrous CoX₂ (X?=?Br^?, SCN^?) and Ni(ClO₄)₂ with N,N,N′,N′-tetraisobutylpyridine-2,6-dithiocarboxamides (S-dbpt), N,N,N′,N′-tetraisopropyl pyridine-2,6-dithiocarboxamides (S-dppt), and N,N,N′,N′-tetraethylpyridine-2,6-dithiocarboxamides (S-dept) lead to the formation of [Co(S-dbpt)Br₂] (1), [Co(S-dppt)(SCN)₂] (2), and [Ni(S-dept)₂]·(ClO₄)₂·H₂O (3), respectively. The X-ray crystal structures of the three S-dapt ligands and three complexes along with spectroscopic analyzes are presented. The molecular structure investigations of the S-dapt ligands show that the thiamide planes are twisted with respect to the pyridine ring, which is more in the case of phenyl groups. The structures of the Co(II) complexes reveal that an increase in steric crowding on the amide side arms of the ligands has no substantial effect on the geometry adopted by the corresponding complexes. The Co(II) gives only 1?:?1 five-coordinate, ion-paired complexes with a distorted square pyramidal geometry. Ni(II), on the other hand, prefers an octahedral geometry with 1?:?2 metal–ligand ratio. The coordination behavior of S-dapt has been compared to the analogous oxo(O-daap) ligands. Lesser propensity of S atom to get involved in H-bonding interactions ensures an S-N-S type of tridentate coordination by S-dapt.     

Synthesis and crystal structure of (E)-[(2-cyclohexenyl) vinyl]triaryltin

(E)-[(2-Cyclohexenyl)vinyl]triaryltin (aryl=phenyl, p-tolyl) were synthesized and characterized by elemental analysis, IR, 1H NMR spectroscopy. The crystal structure of (E)-[(2-cyclohexenyl)vinyl]triphenyltin was also determined by the X-ray diffraction. Experiments show that this compound has the conjugated system, which makes it have possible bioactivity and anti-tumor activity.     

Synthesis and crystal structure of complexes of manganese(II), cobalt(II), and nickel(II) isothiocyanates with ?-caprolactam

The possibility of ?-caprolactam (CPL) to coordinate to manganese(II), cobalt(II), and nickel(II) rhodanides has been investigated. New complexes trans-[M(CPL)₄(NCS)₂], where M = Mn (I), Co (II), and Ni (III), have been synthesized. The complexes have been studied by chemical analysis and IR spectroscopy. According to X-ray diffraction, complexes are isostructural to each other and crystallize in monoclinic space group P2₁/c, Z = 2. For I: a = 6.9457(2) ?, b = 17.7751(6) 0A, c = 12.8999(4) 0A, ?? = 104.2670(10)°, V = 1543.51(8) ?³, ??_calc = 1.342 g/cm³, R ₁ = 0.0426. For II: a = 6.8925(2) ?, b = 17.8189(8) ?, c = 12.7278(6) ?, ?? = 104.421(2)°, V = 1513.93(11) ?³, ??_calc = 1.377 g/cm³, R ₁ = 0.0280. For III: a = 6.7804(2) ?, b = 18.4631(4) ?, c = 12.4841(3) ?, ?? = 105.2950(10)°, V = 1507.49(7) ?³, ??_calc = 1.382 g/cm³, R ₁ = 0.0273. Structures I?CIII are molecular; the metal atom in each of them coordinates four CPL molecules and two NCS groups via oxygen and nitrogen atoms, respectively.     

Synthesis and crystal structure of a trinuclear copper(II) complex derived from N,N′-Bis(4-methoxysalicylidene)-1,3-pentanediamine

A trinuclear copper(II) complex [Cu₃Cl₂L₂], where L is the dianionic form of N,N′-bis(4-methoxysalicylidene)-1,3-pentanediamine, has been synthesized and characterized by means of spectroscopic methods and single crystal X-ray structure determination. The complex crystallizes in the orthorhombic space group Pnma with unit cell dimensions a = 15.301(2), b = 23.226(2), c = 12.089(1)Å, V = 4296.2(8) ų, Z = 4, R ₁ = 0.0682, and wR ₂ = 0.1590. The molecule of the complex possesses a crystallographic mirror plane symmetry with the mirror plane passes through the three Cu atoms and the two Cl atoms. The two terminal Cu atoms adopt distorted square pyramidal coordination, and the middle one adopts square planar coordination. The intramolecular Cu…Cu distances are 2.900(1) and 2.916(1) Å. The complex was tested for its antibacterial activity to assess its inhibiting potential.     

Molecular and crystal structure of iron(III) and nickel(II) complexes with 1′-phthalazinylhydrazones of heterocyclic carbonyl compounds

Journal of Structural Chemistry - The structures of iron(III) and nickel(II) complexes with the composition [FeL2]Cl·H2O (1) and [Ni(HL′2)]·DMSO·0.5H2O (2), where L and...     

Synthesis and crystal structure of dinuclear nickel (Ⅱ) complex

The crystal structure of Ni(Ⅱ) complex with 3-hydroxyl-1, 5-diazacycloheptane-N, N'-diacetate was determined by X-ray diffraction method. Crystal data for Ni2 (C9H14N2O5)2·2H2O: monoclinic, space group P21/n, a = 1.1717(5), b = 0.9794(3), c = 1.2971(2) nm, β= 96.62(3), V= 1.4786(7) nm3, Dc = 1.377 g/cm3, Z = 2,μ=13.321 cm-1 (Mo-Kα), F(000)=640. The final R and Rw are 0.075 and 0.089 respectively. The Ni(Ⅱ) ion forms 2:2 complex with ligand. Two ligands are bridged by two Ni(Ⅱ) atoms which are bridged by two O atoms. Every Ni(Ⅱ) is coordinated by two N atoms and four 0 atoms. The coordination polyhedron of the Ni(Ⅱ) ion is a distorted octahedron.     

Cobalt(III), nickel(II) and copper(II) complexes of N,N′-didodecildithiooxamide

The complexes of N,N′-didodecildithiooxamide (L): CoL₃(ClO₄)₃, NiL₂X₂ (X = Cl, Br, I, ClO₄, HSO₄), CuL₂X₂ (X = ClO₄, HSO₄) and CuLX₂ (X = Cl, Br) were prepared. The cobalt and nickel complexes are diamagnetic, with octahedral and planar coordination respectively. The copper complexes are paramagnetic with normal magnetic moments corresponding to a tetragonal coordination. The i.r. and far i.r. spectra are discussed.     

Synthesis,characterization, and crystal structure of Ni(II) and Cu(II) complexes with N-furoyl-N′,N′-diethylthiourea: antifungal activity

The complexes cis-bis(N-furoyl-N′,N′-diethylthioureato-k ²O,S)nickel(II) and cis-bis(N-furoyl-N′,N′-diethylthioureato-k ²O,S)copper(II) were prepared by the reaction of metal acetate with the corresponding acylthiourea derivative. The complexes were characterized by IR, ¹H-NMR, ¹³C-NMR, and single-crystal X-ray diffraction. Both complexes show two furoylthiourea ligands bonded to metal to form a four-coordinate complex with square-planar geometry. The antifungal activity of the prepared complexes was studied against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides, responsible for important plant diseases.     

Synthesis and crystal structure of new cobalt(II) and copper(II) complexes with deprotonated N -[2′-(4-methyl) pyrimidinyl]-2-nitrobenzenesulfonylurea

Cobalt(II) and copper(II) complexes with deprotonated N-[2′-(4-methyl)pyrimidinyl]-2-nitrobenzenesulfonylurea were synthesized and their structures were characterized by IR spectrum, elemental analysis and X-ray diffraction. The deprotonated sulfonylurea is a bidentate ligand to Co(II) or Cu(II) in octahedral geometry. In the packing diagrams of the complexes, C–H ··· O hydrogen bonds are observed. The UV and fluorescence spectra of the complexes are described, and the thermogravimetric analyses of the complexes were performed.     

Synthesis and crystal structure of lanthanum(III) Iodomercurate(II) complexes with ɛ-Caprolactam

The X-ray diffraction study of the crystalline products of the reaction between potassium tetraiodomercurate(II), ?-caprolactam, and lanthanum(III) nitrate at a ratio of 3: 16: 2 in an aqueous solution has shown the presence of the following three new crystalline compounds: [LaCpl₈]₂[HgI₄]₃ (I), [LaCpl₈][HgI₄]I₃ (II), and [LaCpl₇(H₂O)]₂[HgI₄]₂[Hg₂I₆] (III), where Cpl is ?-caprolactam ?-C₆H₁₁NO. Compounds I and II crystallize in tetragonal crystal system, space groups P4₂/n and $I\bar 4$ , respectively. For compound I, a = 18.59320(10) Å, c = 19.5782(3) Å, V = 6738.32(12) ų, Z = 2, and ρ_calc = 2.067 g/cm³. For compound II, a = 13.2245(10) Å, c = 20.0310(3) Å, V = 3503.17(6) ų, Z = 2, ρ_calc = 2.022 g/cm³. The crystals of compound III are monoclinic (space group P _{2 1}/n, a = 20.1202(6) Å, b = 14.0569(4) Å, c = 46.3228(12) Å, β = 93.4770(10)°, V = 13077.3(6) ų, Z = 4, ρ_calc = 2.274 g/cm³). [La(Cpl)₈]₂[Hg₂I₆]₃ (IV), a new double ionic complex salt, has also been synthesized and studied by X-ray diffraction. The crystals of compound IV are triclinic (space group $P\bar 1$ , a = 12.5021(3) Å, b = 14.6436(3) Å, c = 21.4695(4) Å, α = 84.2300(10)°, β = 87.2230(10)°, γ = 74.9970(10)°, V = 3776.30(14) ų, Z = 1, ρ_calc = 2.452 g/cm³). All complexes have a dicrete ionic structure, and the nearest surrounding of a La atom is distorted square-prismatic or trigonal-dodecahedral. The crystal packing of cations is distorted face-centered cubic (I and II) or body-centered cubic (III and IV) with anions located in its cavities.     

Synthesis and crystal structure of nickel(Ⅱ) and zinc(Ⅱ) complexes with 2,4-bis(3,5-dimethylpyrazol-1-yl)-6-methoxyl-1,3,5-triazine

2,4-Bis(3,5-dimethylpyrazol-1-yl)-6-methoxyl-1,3,5-triazine(bpt) has been synthesized by using a new, simple and general method with high yields. Reactions of bpt with Ni(CIO4)2 · 6H2O and Zn(CIO4)2 · 6H2O in methanol gave mononuclear complex [Ni(bpt)2] · (CIO4)2 · H2O and ternary complex [Zn(mpt)2(dmp)](CIO4)2 respectively, where mpt (2,4-dimethoxy-6-(3,5-dimethyl-pyrazol-1-yl)-1,3,5-triazine) and dmp(3,5-dimethylpyrazole) are the alcoholysis products of bpt in the presence of Zn2+ ion. A possible mechanism for this catalytic reaction was proposed. X-ray crystal structure for ligand bpt, Ni and Zn complexes are reported. The protonated form of the ligand bpt crystallizes as its perchlorate salt including one molecule of water, [Hbpt · H2O · CIO4]. The proton is located on one pyrazole N-atom. [Hbpt ?H2O ?CIO4], in which [Hbpt]+ is in cis-cis conformation, are packed in slipped stacks of approximately parallel layers. The π-π overlap interactions between the non-protonized pyrazoles of the adjace