期刊论文详细信息
Chemistry Central Journal
Importance of halide involving interactions at Hoogsteen sites in supramolecular architectures of some coordination metal complexes of N6-benzyl/furfuryl adenine
Samson Jegan Jennifer1  Packianathan Thomas Muthiah1  Duraiswamy Tamilselvi1 
[1] School of Chemistry, Tiruchirappalli-620024, Tamil Nadu, India
关键词: Supramolecular architectures;    Crystal structures;    X-ray diffraction studies;    N6-furfuryladenine;    N6-benzyladenine;   
Others  :  1213790
DOI  :  10.1186/s13065-014-0058-z
 received in 2014-06-02, accepted in 2014-09-02,  发布年份 2014
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【 摘 要 】

Background

Most of the benzyladenine and furfuryladenine derivatives inhibit tumor/cancer cell growth; their toxicity is lesser than the compounds used for the treatment of cancer now-a-days. Many cytokinin derivatives are tested for anticancer activity.

Results

A series of transition metal complexes containing N6-benzyl/furfuryl aminopurines of formula [Mn(FAH)2(H2O)(Cl3)]2.Cl2(1), [Co(FAH)2(H2O)(Cl3)]2.Cl2(2), [Co(FAH)2(Cl4)]2 .[Co(FAH)2(H3O)(Cl3)].Cl2(3), [Ni(FAH)2(H2O)(Cl3)]2.Cl2. (H2O) (4), [Zn(BAH)Br3] (5) and [Cd2(BAH)2(?-Br)4Br2]n(6) (where BAH and FAH benzyladeninium and furfuryladeninium cations respectively) have been synthesized and characterized. Crystal structures of (1-4) have similar distorted octahedral coordination geometry, while (5) and (6) have distorted tetrahedral geometry and octahedral geometries respectively. In (1-4) two halide ions and two cytokinin cations (BAH+/FAH+) are laterally coordinated to the metal ion. A water molecule and a halide ion are axially coordinated. But the coordination sphere of (5) consists of N7 coordinated benzyladeninium ion and three halide ions. The complex (6) is a coordination polymer bridged by bromide anions. A common notable feature in (1-4) is the presence of one or more lattice chloride anions. They help in a chain formation by N-H¿Cl halide involving hydrogen bonding interactions in between the Hoogsteen site hydrogen.

Conclusions

The observed crystal structures emphasize the role of the halide ions in developing the supramolecular architectures by halide involving hydrogen bonding interactions. Also most of the reported cobalt cytokinin complexes possess tetrahedral coordination geometry, but some cobalt complexes have distorted octahedral coordination geometry, which are discussed and compared.

【 授权许可】

   
2014 Jennifer et al.; licensee Springer.

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【 参考文献 】
  • [1]Jenniefer SJ, Muthiah PT: Supramolecular architectures of two novel organic-inorganic hybrid materials containing identical monomeric uranyl units. Acta Cryst C 2011, 67:m69-m72.
  • [2]Hoffmann F, Cornelius M, Morell J, Fröba M: Silica?based mesoporous organic¿inorganic hybrid materials. Angew Chem Int Ed 2006, 45:3216-3251.
  • [3]Lee SJ, Lin W: Chiral metallocycles: rational synthesis and novel applications. Acc Chem Res 2008, 41:521-537.
  • [4]Lu WG, Jiang L, Feng XL, Lu TB: Three-dimensional lanthanide anionic metal???organic frameworks with tunable luminescent properties induced by cation exchange. Inorg Chem 2009, 48:6997-6999.
  • [5]Tagami H, Uchida S, Mizuno N: Inorganic hybrids size-selective sorption of small organic molecules in One-dimensional channels of an ionic crystalline organic¿inorganic hybrid compound stabilized by ?¿? interactions. Angew Chem Int Ed 2009, 48:6160-6165.
  • [6]Alkordi MH, Brant JA, Wojtas L, Kravtsov VC, Cairns AJ, Eddaoudi M: Zeolite-like metal???organic frameworks (ZMOFs) based on the directed assembly of finite metal???organic cubes (MOCs). J Am Chem Soc 2009, 131:17753-17755.
  • [7]Kalnicova A, Travnicek Z, Popa I, Cajan M, Dolezal K: Synthesis, characterization and in vitro cytotoxicity of Co(II) complexes with N6-substituted adenine derivatives: X-ray structures of 6-(4-chlorobenzylamino)purin-di-ium diperchlorate dihydrate and [Co6(?-L6)4Cl8(DMSO)10]?·?4DMSO. Polyhedron 2006, 25:1421.
  • [8]Trávní?ek Z, Klanicová A, Popa I, Rol?ík J: Synthetic, spectral, magnetic and in vitro cytotoxic activity studies of cobalt (II) complexes with cytokinin derivatives: X-ray structure of 6-(3-methoxybenzylamino) purinium chloride monohydrate. J Inorg Biochem 2005, 99:776-786.
  • [9]Malo? M, Trávn???ek Z, Mary¿ko M, Zbo?il R, Ma¿lá? M, Marek K, Dolezel , Rolcik J, Krystof V, Strnad M: Metal complexes as anticancer agents 2. Iron(III) and copper(II) bio-active complexes with N6-benzylaminopurine derivatives. Inorg Chim Acta 2001, 323:119-129.
  • [10]¿tarha P, Trávní?ek Z, Herchel R, Popa I, Suchý P, Van?o J: Dinuclear copper(II) complexes containing 6-(benzylamino)purines as bridging ligands: Synthesis, characterization, and in vitro and in vivo antioxidant activities. J Inorg Biochem 2009, 103:432-440.
  • [11]Travnicek Z, Malon M, Sindelar Z, Dolezal K, Rolcik J, Krystof V, Strnad M, Marek J: Preparation, physicochemical properties and biological activity of copper(II) complexes with 6-(2-chlorobenzylamino)purine (HL1) or 6-(3-chlorobenzylamino)purine (HL2). The single-crystal X-ray structure of [Cu(H+L2)2Cl3]Cl?·?2H2O. J Inorg Biochem 2001, 84:23-32.
  • [12]Trávn???ek Z, Malo? M, Zatloukal M, Dole¿al K, Strnad M, Marek J: Mixed ligand complexes of platinum(II) and palladium(II) with cytokinin-derived compounds Bohemine and Olomoucine: X-ray structure of [Pt(BohH?+?-N7)Cl3]?·?9/5H2O {Boh =?6-(benzylamino)-2-[(3-(hydroxypropyl)-amino]-9-isopropylpurine. Bohemine}. J Inorg Biochem 2003, 94:307-316.
  • [13]Trávní?ek Z, Popa I, ?ajan M, Zbo?il R, Kry¿tof V, Mikulík J: The first iron(III) complexes with cyclin-dependent kinase inhibitors: Magnetic, spectroscopic (IR, ES?+?MS, NMR, 57Fe Mössbauer), theoretical, and biological activity studies. J Inorg Biochem 2010, 104:405-417.
  • [14]Trávní?ek Z, Malo? M, Biler M, Hajdúch M, Bro¿ P, Dole¿al K, Strnad M: Synthesis, characterization and biological activity of two nickel (II) complexes with 6-(2-chlorobenzylamino) purine. Trans Met Chem 2000, 25:265-269.
  • [15]Trávní?ek Z, Kry¿tof V, ¿ipl M: Zinc (II) complexes with potent cyclin-dependent kinase inhibitors derived from 6-benzylaminopurine: synthesis, characterization, X-ray structures and biological activity. J Inorg Biochem 2006, 100:214-225.
  • [16]Sz??ová L, Trávní?ek Z, Zatloukal M, Popa I: Novel platinum (II) and palladium (II) complexes with cyclin-dependent kinase inhibitors: Synthesis, characterization and antitumour activity. Bioorg Med Chem 2006, 14:479-491.
  • [17]Trávní?ek Z, Marek J: X-ray structural characterizations of the reaction products between ZnCl2 and 6-benzylaminopurine derivatives in different acidic conditions. J Mol Struct 2009, 933:148-155.Z.
  • [18]Novotná R, Trávní?ek Z, Popa I: Synthesis and characterization of the first zinc (II) complexes involving kinetin and its derivatives: X-ray structures of 2-chloro-N6-furfuryl-9-isopropyladenine and [Zn (kinetin)2Cl2]?·?CH3OH. Inorg Chim Acta 2010, 363:2071-2079.
  • [19]Muthiah PT, Mazumdar SK, Chaudhuri S: Metal ions-nucleobases interactions: preparation and crystal structures of trichloroadeninium zinc (ii)(form ii) and a similar zinc complex of arprinocid [6-amino-9-(2-chloro-6-fluorobenzyl) purine]. J Inorg Biochem 1983, 19:237-246.
  • [20]¿poner JE, Leszczynski J, Glahé F, Lippert B, ¿poner J: Protonation of platinated adenine nucleobases. Gas phase vs condensed phase picture. Inorg Chem 2001, 40:3269-3278.
  • [21]Umadevi B, Muthiah PT, Stanley N, Varghese B: Synthesis, characterization and crystal structure of dichlorobis(N6-furfuryladeninium) copper(II) chloride. Indian J Chem Sect A Inorg Bio-inorg Phys Theor Anal Chem 2002, 41:737-740.
  • [22]Balasubramanian TP, Muthiah PT, Ananthasaravanan , Mazumdar SK: Metal-nucleobase interactions: synthesis and crystal structure of trichlorobis(N6-benzyl adeninium) copper(II) chloride dehydrate. J Inorg Biochem 1996, 63:175.
  • [23]Stanley N, Muthiah PT, Luger P, Weber M, Geib SJ: Metal¿nucleobase interactions: Interplay of coordination and hydrogen bonding in cadmium (II) complexes of N6-substituted adenines. Inorg Chem Commun 2005, 8:1056-1059.
  • [24]Trávní?ek Z, Matiková-Ma?arová M: 6-(3-Bromobenzylamino)purin-3-ium chloride. Acta Cryst E 2006, 62:o5097-o5099.
  • [25]APEX2, SAINT and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA; 2008.
  • [26]Sheldrick GM: A short history of SHELX. Acta Cryst A 2008, 64:112-122.
  • [27]Spek AL: Structure validation in chemical crystallography. Acta Cryst D 2009, 65:148-155.
  • [28]Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA: Mercury CSD 2.0 - new features for the visualization and investigation of crystal structures. J Appl Crystallogr 2008, 41:466-470.
  • [29]Umadevi B, Stanley N, Muthiah PT, Bocelli G, Cantoni A: N6-Benzyladenine hydrobromide and the solid-state conformation of cytokinins. Acta E 2001, 57:o881-o883.
  • [30]Xia M, Ma KR, Zhu Y: Synthesis and crystal structure of hydrate adduct of 6-benzylaminopurine and 5-sulfosalicylic acid [(C12H12N5)(C7H5O6S)?·?H2O]. J Chem Crystallogr 2010, 40:634-638.
  • [31]Korszun ZR, Knight C, Chen CM: A stereochemical model for cytokinin activity. FEBS Lett 1989, 243:53-56.
  • [32]Rao P, Ghosh S, Maitra U: Binding of 9-N-butyladenine by carboxylic acids: Evidence that Hoogsteen binding can dominate in solution. J Phys Chem B 1999, 103:4528-4533.
  • [33]Dobrzynska D, Jerzykiewicz LB: Adenine ribbon with Watson-crick and hoogsteen motifs as the ¿double-sided adhesive tape¿ in the supramolecular structure of adenine and metal carboxylate. J Am Chem Soc 2004, 126:11118-11119.
  • [34]Dauter Z, Jaskolski M: How to read (and understand) volume A of international tables for crystallography: an introduction for nonspecialists. J Appl Cryst 2010, 43:1150-1171.
  • [35]Wilkinson HS, Harrison WT: Propane-1, 3-diaminium bis (dihydrogenarsenate). Acta E 2005, 61:m1289-m1291.
  • [36]Cuny J, Gougeon P, Gall P: Redetermination of Zn2Mo3O8. Acta E 2009, 65:i51-i51.
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