Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

Mardani, Zahra; Golsanamlou, Vali; Jabbarzadeh, Zahra; Moeini, Keyvan; Khodavandegar, Saba; Carpenter‐Warren, Cameron L.; Slawin, Alexandra M. Z.; Woollins, J. Derek

doi:10.1080/00958972.2018.1536268

Cited by 18 publications

(17 citation statements)

References 45 publications

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“…This OTP was then reacted with Pb(OAc) 2 • 3H 2 O in branched tubes to give the 2D coordination polymer of 1 in which the OTP ligand is converted to the HME − anion. Similar structural conversion of the ligand during the complexation process was observed for an oxazolidine ligand [29,30].…”

Section: Resultssupporting

confidence: 63%

2D-Coordination polymer containing lead(II) in a hemidirected PbO₄S₃ environment formed by molecular breaking of the 1,3-oxathiolane ligand

Mardani

Akbari

Moeini

et al. 2019

Zeitschrift Für Naturforschung B

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A new 1,3-oxathiolane-based ligand, 2-(1,3-oxathiolan-2-yl)pyridine, was prepared and its coordination to lead(II) was investigated. Experiments revealed a ligand-breaking reaction during the complexation process, which leads to the formation of a 2D-coordination polymer of lead(II), [Pb(μ3-HME)(μ-OAc)]n; H2ME: 2-mercaptoethanol. The compounds have been characterized by elemental analysis, FT-IR, 1H NMR spectroscopy and single-crystal X-ray diffraction. X-ray analysis revealed a 2D-coordination polymer extending via acetato bridges. The lead(II) center adopts a rare PbO4S3-distorted pentagonal bipyramidal geometry with a hemidirected arrangement. Upon coordination, the thiol group of the H2ME ligand is deprotonated to coordinate as an anionic ligand. The network extends in sheets in the crystallographic ab plane via Pb–S–Pb and Pb–O–Pb bridges, aided by O–H⋯O hydrogen bonds.

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Section: Resultssupporting

confidence: 63%

2D-Coordination polymer containing lead(II) in a hemidirected PbO₄S₃ environment formed by molecular breaking of the 1,3-oxathiolane ligand

Mardani

Akbari

Moeini

et al. 2019

Zeitschrift Für Naturforschung B

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“…The angular structural parameter (τ) value for 1 was calculated to be 0.37, indicating a distorted square pyramidal geometry around the copper(II) ion, which is the most common 5-coordinate geometry for a copper(II) ion in complexes such as these [34]. Comparing the axial and equatorial bond lengths confirms slight elongation along the z-axis (the axial Cu-O bond length is 0.249 Å longer than the equatorial Cu-N average), consistent with pseudo Jahn-teller distortions observed in other Cu(II) square pyramidal structures [34,62]. Comparing the geometrical parameters of 1 with its non-ionic analogue, containing an octahedrally coordinated copper(II) ion, [Cu(ACE)(NO3)2] [15], revealed that the Cu-N distance average (2.046 and 2.040 Å for 1 and its analogue, respectively) is similar, whilst the Cu-O distances of the analogue (2.673 Å) are much longer than in 1 (2.2985(2) Å).…”

Section: Crystal Structure Of [Cu(ace)no3]no3 (1)supporting

confidence: 77%

“…In addition to these compounds, the non-ionic analogues of 1 and 2 were added to the docking list. The Gold docking results are reported in terms of the values of fitness, with higher fitness indicating a better docking interaction [32][33][34][35]62]. The results of the docking studies presented in this work are the best binding results out of the ten favorites predicted by Gold.…”

Section: Docking Studiesmentioning

confidence: 85%

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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“…action of the compounds (Marandi, Moeini, Alizadeh, Mardani, Quah, Loh & Woollins, 2018;Mardani, Kazemshoar-Duzduzani et al, 2018;Marandi, Moeini, Arkak et al, 2018;Saghatforoush et al, 2018;Mardani, Golsanamlou et al, 2018;Hakimi et al, 2018). The results of the docking presented in this work are the best binding results out of ten favourites predicted by GOLD.…”

Section: Figurementioning

confidence: 62%

“…Also, for evaluation of the calculated fitness values, these scores were compared with those of the famous anticancer drug doxorubicin [a cancer medication that interferes with the growth and spread of cancer cells in the body (https://www.drugs.com/mtm/doxorubicin.html); Marandi, Moeini, Arkak et al, 2018]. The general features from the GOLD docking prediction (Table 7) show that all the studied structures can be considered as potentially biologically active compounds (Marandi, Moeini, Alizadeh, Mardani, Quah, Loh & Woollins, 2018;Mardani, Kazemshoar-Duzduzani et al, 2018;Mardani, Golsanamlou et al, 2018). The best predicted protein target for PPTA and 1 is TrxR and for 2 is DNA-Gyrase.…”

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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Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

Cited by 18 publications

References 45 publications

2D-Coordination polymer containing lead(II) in a hemidirected PbO₄S₃ environment formed by molecular breaking of the 1,3-oxathiolane ligand

2D-Coordination polymer containing lead(II) in a hemidirected PbO₄S₃ environment formed by molecular breaking of the 1,3-oxathiolane ligand

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

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

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Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

Cited by 18 publications

References 45 publications

2D-Coordination polymer containing lead(II) in a hemidirected PbO4S3 environment formed by molecular breaking of the 1,3-oxathiolane ligand

2D-Coordination polymer containing lead(II) in a hemidirected PbO4S3 environment formed by molecular breaking of the 1,3-oxathiolane ligand

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

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

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2D-Coordination polymer containing lead(II) in a hemidirected PbO₄S₃ environment formed by molecular breaking of the 1,3-oxathiolane ligand

2D-Coordination polymer containing lead(II) in a hemidirected PbO₄S₃ environment formed by molecular breaking of the 1,3-oxathiolane ligand

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