Please use this identifier to cite or link to this item: http://hdl.handle.net/1959.13/33458

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Title
Aminoalcohols incorporating piperazine ring: synthesis, complexation of a hexadentate ligand and DNA cleavage capability of copper(II) complexes
Author/Creator
Griggs, Brendan L.;  Lawrance, Geoffrey A.;  Maeder, Marcel J.;  Robertson, Mark;  Turner, Peter
Institution
The University of Newcastle. Faculty of Science & Information Technology, School of Environmental and Life Science
Description
The facility of aminoalcohol ligand synthesis via ring opening of cyclohexene oxide with polyamines including a piperazine ring is illustrated here with the syntheses and characterization of (2′-hydroxycyclohexyl)piperazine (1), bis(2′-hydroxycyclohexyl)-piperazine (2), 4-{(2″-hydroxycyclohexyl)-2′-aminoethyl)}piperazine (3), 1-(2″-hydroxycyclohexyl)-4-{(2″-hydroxycyclohexyl)-2′-aminoethyl)}piperazine (4), and 1,4-bis[(2″-hydroxycyclohexyl)-3′-aminopropyl]piperazine (5) described, along with an analogue of 4 in which a single –CH₂–CH₂– alkyl chain replaces the piperazine ring, 1,5-bis[(2′-hydroxycyclohexyl)amine]-3-azapentane (6). The viability of 5 as a hexadentate ligand was established by preparation of its copper(II) complex and subsequent X-ray crystal structure analysis. The complex [Cu(5)](ClO₄)₂ cation lies in a distorted octahedral environment with the four nitrogen donors in an approximate plane also incorporating the copper (Cu–Ntert 2.058(4) A; Cu–Nsec 2.072(4) A) and the two alcohol groups occupying axial sites with elongated bonds (Cu–O 2.415(3) A). The piperazine ring adopts a ‘butterfly wing’ geometry, whereas the two cyclohexane rings are in chair conformations. Significant bond angle distortions occur around the copper, exacerbated by the axial Jahn–Teller bond length distortion. The ability of the copper(II) complexes of the aminoalcohols to promote DNA cleavage was examined. Complexes of 2, 3 and 5 are effectively inactive whereas 4 is an efficient single strand cleavage promoter; however, the more flexible close analogue of 4, 6, also proved ineffective. Such observations for a closely related series indicate the subtle influences of spectator ligand rigidity and steric congestion on DNA cleavage promotion.
Relation
Inorganica Chimica Acta Vol. 360, Issue 7, p. 2403-2410
Publisher Link
http://dx.doi.org/10.1016/j.ica.2006.12.025
Date
2007
Publisher
Elsevier BV
Keyword(s)
cyclohexene oxide;  piperazine;  aminoalcohol;  copper(II) complexes;  X-ray crystal structure;  DNA cleavage
Resource Type
journal article
Identifier
http://hdl.handle.net/1959.13/33458
Identifier
ISSN:0020-1693
Reviewed
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Subject
"Inorganica Chimica Acta"
 
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