Synthesis and characterization of two piperazine containing macrocycles and their transition metal complexes

被引:2
作者
Pota, Kristof [1 ]
Johnston, Hannah M. [1 ]
Madarasi, Eniko [2 ,3 ]
Tircso, Gyula [2 ]
Green, Kayla N. [1 ]
机构
[1] Texas Christian Univ, Dept Chem & Biochem, 2950 W Bowie, Ft Worth, TX 76129 USA
[2] Univ Debrecen, Fac Sci & Technol, Dept Phys Chem, Egyet Ter 1, H-4032 Debrecen, Hungary
[3] Univ Debrecen, Doctoral Sch Chem, Egyet Ter 1, H-4032 Debrecen, Hungary
关键词
Piperazine; Macrocycle; Manganese; Log B; Pyridinophane; MOLECULAR-MECHANICS; CRYSTAL-STRUCTURE; MN2+ COMPLEXES; SCHIFF-BASES; LIGANDS; STABILITY; PYRIDINE; CONFORMATION; PROTONATION; RELAXATION;
D O I
10.1016/j.jinorgbio.2023.112124
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Rigidification of the ligand scaffolds has been a particular mechanism of interest employed to achieve properties suitable for MRI contrast, catalysis, or other applications of metal complexes. Towards the goal of targeting a 15-anePyN5Pip type ligand, a serendipitous isolation of a 30-anePy2N10Pip2 aza-macrocycle was achieved, instead. X-ray diffraction and determination of pKa events were carried out and compared to 17-anePyN5Pip. Further-more, the X-ray diffraction of the Cu(II) and Zn(II) complexes of 17-anePyN5Pip was achieved and compared to previous reports of other first-row transition metal derivatives of this ligand. Determination of the log beta with both 30-anePy2N10Pip2 and 17-anePyN5Pip with the divalent Mn-Zn metal-ion series was used to demonstrate the impact that the piperazine ring plays compared to other, less rigid macrocycles reported to date.
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页数:9
相关论文
共 57 条
[1]   SYNTHESIS, STRUCTURE, AND SPECTROSCOPIC PROPERTIES OF COPPER(II) COMPOUNDS CONTAINING NITROGEN SULFUR DONOR LIGANDS - THE CRYSTAL AND MOLECULAR-STRUCTURE OF AQUA[1,7-BIS(N-METHYLBENZIMIDAZOL-2'-YL)-2,6-DITHIAHEPTANE]COPPER(II) PERCHLORATE [J].
ADDISON, AW ;
RAO, TN ;
REEDIJK, J ;
VANRIJN, J ;
VERSCHOOR, GC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1984, (07) :1349-1356
[2]   SYNTHESIS AND COORDINATION CHEMISTRY OF 2 PENTA-AZAMACROCYCLES CONTAINING A 1,4-PIPERAZINE BACKBONE - CRYSTAL-STRUCTURE DETERMINATIONS OF 6,12-DIOXO-1,5,13,17,22-PENTA-AZATRICYCLO[15.2.2.17,11]DOCOSA-7(22),8,10-TRIENE AND 1,5,13,17,22-PENTA-AZATRICYCLO[15.2.2.17,11]DOCOSA-7(22),8,10-TRIENENICKEL(II) PERCHLORATE2 [J].
ALCOCK, NW ;
MOORE, P ;
READER, CJ ;
ROE, SM .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1988, (12) :2959-2963
[3]   Late First-Row Transition-Metal Complexes Containing a 2-Pyridylmethyl Pendant-Armed 15-Membered Macrocyclic Ligand. Field-Induced Slow Magnetic Relaxation in a Seven-Coordinate Cobalt(II) Compound [J].
Antal, Peter ;
Drahos, Bohuslav ;
Herchel, Radovan ;
Travnicek, Zdenek .
INORGANIC CHEMISTRY, 2016, 55 (12) :5957-5972
[4]   Polyfunctional Recognition of Pyridinedicarboxylate Anions with Macrocyclic Polyamine Receptors Containing Heteroaromatic Groups [J].
Bazzicalupi, Carla ;
Bencini, Andrea ;
Bianchi, Antonio ;
Borri, Claudia ;
Danesi, Andrea ;
Garcia-Espana, Enrique ;
Giorgi, Claudia ;
Valtancoli, Barbara .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8286-8295
[5]   Oxalate-templated synthesis of di-zinc macrocycles [J].
Beattie, Jeffrey W. ;
SantaLucia, Daniel J. ;
White, David S. ;
Groysman, Stanislav .
INORGANICA CHIMICA ACTA, 2017, 460 :8-16
[6]  
Carey F.A., 2010, Organic Chemistry, V8th
[7]  
Chan W.C., 2000, FMOC SOLID PHASE PEP, P24
[8]  
Clayden J., 2012, Organic Chemistry
[9]   Thermodynamic stability and relaxation studies of small, triaza-macrocyclic Mn(II) chelates [J].
de Sa, Arsenio ;
Bonnet, Celia S. ;
Geraldes, Carlos F. G. C. ;
Toth, Eva ;
Ferreira, Paula M. T. ;
Andre, Joao P. .
DALTON TRANSACTIONS, 2013, 42 (13) :4522-4532
[10]   Water exchange on seven-coordinate Mn(II) complexes with macrocyclic pentadentate ligands: Insight in the mechanism of Mn(II) SOD mimetics [J].
Dees, Anne ;
Zahl, Achim ;
Puchta, Ralph ;
Hommes, Nico J. R. van Eikema ;
Heinemann, Frank W. ;
Ivanovic-Burmazovic, Ivana .
INORGANIC CHEMISTRY, 2007, 46 (07) :2459-2470