Synthesis and characterization of a macrocyclic copper complex containing the 14-membered 1,3,5,8,10,12-hexaazacyclotetradecane unit

Hakimi, Mohammad; Mardani, Zahra; Moeini, Keyvan; Mohr, Fabian

doi:10.1515/znb-2016-0199

Cited by 9 publications

(2 citation statements)

References 34 publications

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“…The PPTA ligand and the O-donor atoms of the nitrate ligands occupy equatorial positions [with bond lengths in the range 1.9632 (13)-1.9993 15 Table 2). The axial bond length is 0.25 Å longer than the equatorial bond lengths due to the Jahn-Teller effect (Hakimi et al, 2012(Hakimi et al, , 2017. In addition, there might be weak interactions with the O atoms of the nitrate ligands [Cu1Á Á ÁO3 = 2.884 (2) Å and Cu1Á Á ÁO6 = 2.6561 (15) Å ].…”

Section: Figurementioning

confidence: 99%

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

Marandi¹,

Moeini²,

Krautscheid³

2019

Acta Crystallogr C

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Two complexes of 5‐phenyl‐3‐(pyridin‐2‐yl)‐1,2,4‐triazine (PPTA), namely (ethanol‐κO)bis(nitrato‐κO)[5‐phenyl‐3‐(pyridin‐2‐yl‐κN)‐1,2,4‐triazine‐κN2]copper(II), [Cu(NO3)2(C14H10N4)(C2H6O)] or [Cu(NO3)2(PPTA)(EtOH)] (1), and bis[μ‐5‐phenyl‐3‐(pyridin‐2‐yl)‐1,2,4‐triazine]‐κ3N1:N2,N3;κ3N2,N3:N1‐bis[(nitrato‐κO)silver(I)], [Ag2(NO3)2(C14H10N4)2] or [Ag2(NO3)2(μ‐PPTA)2] (2), were prepared and characterized by elemental analysis, FT–IR spectroscopy and single‐crystal X‐ray diffraction. The X‐ray structure analysis of 1 revealed a copper complex with square‐pyramdial geometry containing two O‐donor nitrate ligands along with an N,N′‐donor PPTA ligand and one O‐donor ethanol ligand. In the binuclear structure of 2, formed by the bridging of two PPTA ligands, each Ag atom has an AgN3O environment and square‐planar geometry. In addition to the four dative interactions, each Ag atom interacts with two O atoms of two nitrate ligands on adjacent complexes to complete a pseudo‐octahedral geometry. Density functional theory (DFT) calculations revealed that the geometry around the Cu and Ag atoms in 1opt and 2opt (opt is optimized) for an isolated molecule is the same as the experimental results. In 1, O—H…O hydrogen bonds form R12(4) motifs. In the crystal network of the complexes, in addition to the hydrogen bonds, there are π–π stacking interactions between the aromatic rings (phenyl, pyridine and triazine) of the ligands on adjacent complexes. The ability of the ligand and complexes 1 and 2 to interact with ten selected biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II and B‐DNA) was investigated by docking studies. The results show that the studied compounds can interact with proteins better than doxorubicin (except for TrxR and Top II).

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Section: Figurementioning

confidence: 99%

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

Marandi¹,

Moeini²,

Krautscheid³

2019

Acta Crystallogr C

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“…In another survey, all macrocyclic complexes of ACE were investigated. This study revealed that there are nine compounds; six ACE/Cu examples [14,15,56] and three ACE/Ni ones [57][58][59]. In all complexes, the ACE ligand act as N4-donor (N1, N5, N8 and N12, Scheme 1) except in one case [14] in which in addition to the four nitrogen atoms of ACE, one of the side nitrogen atoms of the macrocyclic ligand (N3 or N10, Scheme 1) also participates in complexation reaction.…”

Section: Description Of the Crystal Structuresmentioning

confidence: 98%

Macrocyclic copper(II) complexes containing diazacyclam-based ligand: spectral, structural and docking studies

Mardani

Moeini

Darroudi

et al. 2019

Journal of Coordination Chemistry

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The macrocyclic copper complex, [Cu(ACE)(NO3)2]; ACE: 1,3,6,10,12,15hexaazatricyclo[13.3.1.1 6,10 ]eicosane, was synthesized by template condensation from a mixture of N 1-(2-aminoethyl)-1,3-diaminopropane, formaldehyde and copper(II) nitrate. Replacement of the nitrate with thiocyanato and azido ligands gives [Cu(ACE)NSC]NSC (2) and the 1Dcoordination polymer, [Cu(ACE)(μ-N3)]n[N3]n (3), respectively. Complex 1, [Cu(ACE)(NO3)]NO3, is an intermediate product in which one of the nitrate ions is separated from its parent molecule. Formation of 1 allow us to conclude that the mechanism of ion exchange reactions on its parent molecule is similar to SN1. These complexes have been characterized by FT-IR spectroscopy and X-ray crystallography. In the crystal structures of 1 and 2, the copper(II) ion has a distorted square pyramidal geometry in which the N4-donor ACE ligand lies on the equatorial plane and other ligand occupies the axial position. The copper(II) ion in 3 has an octahedral geometry, coordinating to one ACE ligand in the equatorial plane and two N-donor bridging azido groups in the axial positions. In all structures, owing to the Jahn-Teller effect, the coordinated bond length of the axial position is longer than the equatorial ones. The ability of ACE ligand and its complexes 1 and 2, along with their analogues, to interact with ten selected biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II, B-DNA) was investigated by docking calculations and compared with that of doxorubicin.

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Template synthesis of a rare 14-membered macrocyclic complex using cadmium(II) ion as a collector

Dorjani

Mardani

Moeini

et al. 2022

J Incl Phenom Macrocycl Chem

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Synthesis and characterization of a macrocyclic copper complex containing the 14-membered 1,3,5,8,10,12-hexaazacyclotetradecane unit

Cited by 9 publications

References 34 publications

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

Macrocyclic copper(II) complexes containing diazacyclam-based ligand: spectral, structural and docking studies

Template synthesis of a rare 14-membered macrocyclic complex using cadmium(II) ion as a collector

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Synthesis and characterization of a macrocyclic copper complex containing the 14-membered 1,3,5,8,10,12-hexaazacyclotetradecane unit

Cited by 9 publications

References 34 publications

Coordination of a triazine ligand with CuII and AgI investigated by spectral, structural, theoretical and docking studies

Coordination of a triazine ligand with CuII and AgI investigated by spectral, structural, theoretical and docking studies

Macrocyclic copper(II) complexes containing diazacyclam-based ligand: spectral, structural and docking studies

Template synthesis of a rare 14-membered macrocyclic complex using cadmium(II) ion as a collector

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Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies