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Synthesis, characterization, and antibacterial activity of the ligands including thiophene/furan ring systems and their Cu(II), Zn(II) complexes

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Abstract

Carboxamide complexes having general formula as [ML]Cl2·nH2O (where M = Cu(II), Zn(II); n = 0, 1/2) were synthesized using heterocyclic carboxamide ligands: 1,4-bis[3-(2-thiophenecarboxamido)propyl]piperazine (L1) and 1,4-bis[3-(2-furancarboxamido) propyl]piperazine (L2). Their structures were characterized with elemental analysis, molar conductivity, magnetic susceptibility, and spectral methods (1H-NMR, 13C-NMR, FT-IR, LC-MS). TGA and DTA curves were also performed. The structure–activity relationship for the ligands was investigated using PM3 semi-empirical method. The antibacterial activities of the carboxamides and their complexes were investigated against bacteria; Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 11230, Bacillus magaterium RSKK 5117, B. cereus RSKK 863, Salmonella enteritidis ATCC 13076, B. subtilis RSKK 244 using microdilution method.

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References

  • Akinchan NT, Drozdzewski PM, Akinchan R (2001) Synthesis, nuclear magnetic resonance and infrared studies of zinc(II) and cadmium(II) complexes of thiosemicarbazones derived from fluorenone and p-anisaldehyde. Polish J Chem 76:1381–1387

    Google Scholar 

  • Al-Hıari YM, Sweileh BA (2006) Synthesis, 3,7-dimethyl phenoxathiin, 3,7-dimethyl phenoxathiin-1O-oxide, 3,7-dimethyl phenoxatbiinly-lO-dioxide, dihydroxyditolyl sulphones, antimicrobial activity. Asian J Chem 18:2285–2298

    Google Scholar 

  • Alves CN, Pinheiro JC, Camargo AJ, Ferreira MMC, Silva ABF (2000) A structure activity relationship study of HEPT-analog compounds with anti-HIV activity. J Mol Struct (Theochem) 530:39–47

    Article  CAS  Google Scholar 

  • Alyar S, Özbek N, Kuzukıran K, Karacan N (2011) Quantitative structure–activity relationships studies for prediction of antimicrobial activity of synthesized disulfonamide derivatives. Med Chem Res 20:175–183

    Article  CAS  Google Scholar 

  • Auzeil N, Largeron M, Fleury MB (1999) Acid-catalysed N-alkyl heterolysis of tertiary pyridinecarboxamides and benzamides under mild conditions. J Chem Soc Perkin Trans 2:1703–1710

    Google Scholar 

  • Balaban Gündüzalp A, Erk B (2010) Copper(II) and zinc(II) complexes of thiophene/furan carboxamides: synthesis, structure and properties. Russ J Inorg Chem 55:1094–1102

    Article  Google Scholar 

  • Balaban A, Çolak N, Ünver H, Erk B, Durlu TN, Zengin DM (2008) Synthesis, spectroscopic studies and crystal structure of N,N′-bis((thiophene-2-carboxamido)propyl)piperazine. J Chem Crystallogr 38:369–372

    Article  CAS  Google Scholar 

  • Balasubramanian KP, Parameswari K, Chinnusamy V, Prabhakaran R, Natarajan K (2006) Synthesis, characterization, electro chemistry, catalytic and biological activities of ruthenium(III) complexes with bidentate N, O/S donor ligands. Spectrochim Acta A 65:678–683

    Article  CAS  Google Scholar 

  • Barnes DJ, Chapman RL, Stephens FS, Vagg RS (1981) Studies on the metal amide bond. VII. Metal complexes of the flexible N4 ligand N,N′-bis(2′-pyridinecarboxamide)1,2-ethane. Inorg Chim Acta 51:155–162

    Article  CAS  Google Scholar 

  • Chapman RL, Vagg RS (1979) Studies on the metal-amide bond. I. Metal complexes of the bis-amide tetradentate ligand N,N′-bis(2′-pyridinecarboxamide)-1,2-benzene. Inorg Chim Acta 33:227–234

    Article  CAS  Google Scholar 

  • Deeb O, Hemmateenejad B, Jaber A, Garduno-Juarez R, Miri R (2007) Effect of the electronic and physicochemical parameters on the carcinogenesis activity of some sulfa drugs using QSAR analysis based on genetic-MLR and genetic-PLS. Chemosphere 67:2122–2130

    Article  PubMed  CAS  Google Scholar 

  • El-Jouad A, Riou M, Allain MA, Khan G, Bouet M (2001) Synthesis, structural and spectral studies of 5-methyl 2-furaldehyde thiosemicarbazone and its Co, Ni, Cu and Cd complexes. Polyhedron 20:67–74

    Article  Google Scholar 

  • Gudasi KB, Vadavi RS, Shenoy RV, Patil MS, Patil SA (2005) Ambidentate behavior of pentadentate N,N′-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide towards transition metal(II) salts. Trans Met Chem 30:569–574

    Article  CAS  Google Scholar 

  • Hamurcu F, Balaban Gündüzalp A, Çete S, Erk B (2008) The synthesis, characterization and antimicrobial activity of N,N0-bis(2-thiophenecarboxmido)-1,3-diaminopropane and N,N0-bis (2-furancarboxamido)-1,3-diaminopropane and their Cu(II), Zn(II), Co(III) complexes. Trans Metal Chem 33:137–141

    Article  CAS  Google Scholar 

  • Ibrahim G, Khan MA, Richomma M, Benali-Baitich O, Bouet G (1997) Synthesis and characterization of metallic complexes of 3-(2-furyl) 2-propenal semicarbazone with d element dihalides. Polyhedron 16:3455–3461

    Article  CAS  Google Scholar 

  • Ibrahim G, Chebli E, Khan MA, Bouet GM (1999) Metallic complexes from 2-furaldehyde semicarbazone and 5-methyl-(2-furaldehyde) semicarbazone. Trans Met Chem 24:294–298

    Article  CAS  Google Scholar 

  • Ibrahim G, Khan MA, Bouet GM (2002) Complexes of 2-furaldehyde-4-phenylsemicarbazone. Trans Met Chem 27:34–37

    Article  CAS  Google Scholar 

  • Iriepa I, Madrid AI, Galvez E, Bellanato J (2006) Synthesis, structural and conformational study of some amides derived from N-methylpiperazine. J Mol Struct 787:8–13

    Article  CAS  Google Scholar 

  • Keskioğlu E, Balaban Gündüzalp A, Çete S, Hamurcu F, Erk B (2008) Cr(III), Fe(III) and Co(III) complexes of tetradentate (ONNO) Schiff base ligands: synthesis, characterization, properties and biological activity. Spectrochim Acta A 70:634–640

    Article  Google Scholar 

  • Lameira J, Alves CN, Moliner V, Silla E (2006) A density functional study of flavonoid compounds with anti-HIV activity. Eur J Med Chem 41:616–623

    Article  PubMed  CAS  Google Scholar 

  • Mitchell DD, Pickens JC, Korotkov K, Fan E, Hol WGJ (2004) 3,5-Substituted phenyl galactosides as leads in designing effective cholera toxin antagonists: synthesis and crystallographic studies. Bioorg Med Chem 12:907–920

    Article  PubMed  CAS  Google Scholar 

  • Mohamed GG (2006) Synthesis, characterization and biological activity of bis(phenylimine) Schiff base ligands and their metal complexes. Spectrochim Acta A 64:188–195

    Article  Google Scholar 

  • Mohamed GG, Omar MM, Hindy AMM (2005) Synthesis, characterization and biological activity of some transition metals with Schiff base derived from 2-thiophene carboxaldehyde and aminobenzoic acid. Spectrochim Acta A 62:1140–1150

    Article  Google Scholar 

  • Nawar N, Hosny NM (1999) Reaction of ruthenium carbonyl cluster complex with multidentate phosphine ligand; preparation of bis(diphenylphosphino)amine, and the X-ray crystal structure of [Ru3(CO)10(dppa)] (dppa = Ph2PN(H)PPh2). Chem Pharm Bull 47:944–949

    Article  PubMed  CAS  Google Scholar 

  • Nawar N, Hosny NM (2000) Synthesis, spectral and antimicrobial activity studies of o-aminoacetophenone o-hydroxybenzoylhydrazone complexes. Trans Met Chem 25:1–8

    Article  CAS  Google Scholar 

  • Ouyang X, Armstrong R, Murphy MM (1998) A novel cleavage technique to generate small molecule compounds and libraries via a two-resin system. J Org Chem 63:1027–1032

    Article  CAS  Google Scholar 

  • Özbek N, Katırcıoğlu N, Karacan N, Baykal T (2007) Synthesis, characterization and antimicrobial activity of new aliphatic sulfonamide. Bioorg Med Chem 15:5105–5109

    Article  PubMed  Google Scholar 

  • Özmen ÜÖ, Olgun G (2008) Synthesis, characterization and antibacterial activity of new sulfonyl hydrazone derivatives and their nickel(II) complexes. Spectrochim Acta A 70:641–645

    Article  Google Scholar 

  • Seeber G, Kariuki BM, Cronin L, Kögerler P (2005) Synthesis, structure and magnetism of a linear Cu-Cl-Cu entity found in [(Cu(tachH)(tach))2(μ-Cl)]5+. Polyhedron 24:1651–1655

    Article  CAS  Google Scholar 

  • Stephens FS, Vagg RS (1988) Studies on the metal-amide bond. XX. A structural comparison of an unusual dimeric cobalt(III) complex, fac-[Co2(bpen)3]·12H2O, with the free ligand N,N′-bis(2′-pyridinecarboxamide)-1,2-ethane, bpenH2. Inorg Chim Acta 142:43–50

    Article  CAS  Google Scholar 

  • Stubbe J, Kozarich JW (1987) Mechanisms of bleomycin-induced DNA degradation. Chem Rev 87:1107–1136

    Article  CAS  Google Scholar 

  • Venkatachalam G, Ramesh R (2005) Catalytic and biological activities of Ru(III) mixed ligand complexes containing N,O donor of 2-hydroxy-1-naphthylideneimines. Spectrochim Acta A 61:2081–2087

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors thank the Gazi University, vide Project no (05/2007–09) for financial support.

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Correspondence to Ayla Balaban Gündüzalp.

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Balaban Gündüzalp, A., Özbek, N. & Karacan, N. Synthesis, characterization, and antibacterial activity of the ligands including thiophene/furan ring systems and their Cu(II), Zn(II) complexes. Med Chem Res 21, 3435–3444 (2012). https://doi.org/10.1007/s00044-011-9878-8

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