Synthesis, Characterization and Biological Activities of Novel a 1,2,3,4-tetrahydroquinazoline and Its Nickel(II) Complexes

Abstract

The 2-methyl-2-(1-hydroxyiminoethyl)-1,2,3,4-tetrahydroquinazoline (HL or 1) and its novel Ni(II) complexes, square-planar [Ni(L)(LH)]·(NO₃) (2) and octahedral [NiCl₂(LH)(H₂O)₂]·(H₂O) (3), have been synthesized. The ligand and complexes have been characterized by means of elemental, IR, UV-Vis. spectroscopic studies, ¹H-NMR, ¹³C-NMR, magnetic susceptibility, thermal analysis, mass spectroscopy and X-ray diffraction technique. The HL ligand crystallizes in the P2₁/c. Antimicrobial activity of ligand (1) and complexes (2 and 3) was evaluated by the agar diffusion method. Complex 2 showed weak antimicrobial activity against tested microorganism strains. Complex 3 exhibited moderate antimicrobial activity against Staphylococcus epidermidis and Candida albicans.

Keywords

• antimicrobial activity
• nickel complex
• oxime
• 1
• 2
• 3

References

1. Reference 1 W. H.Correa, S. Papadopoulos, P. Radnidge, B. A. Roberts, J. L. Scott, Green Chem. 2002, 4, 245-251. Reference 2 A. Göblöys, L. Lázár, F. Fülöp, Tetrahedron 2002, 58, 1011-1016. Reference 3 J. Sinkkonen, K. N. Zelenin, A. K. A. Potapov, I. V. Lagoda, V. V. Alekseyev, K. Pihlaja, Tetrahedron 2003, 59, 1939-1950. Reference 4 K. Tanaka, R. Shiraishi, Green Chem. 2000, 2, 272-273. Reference 5 A. T. Çolak, M. Taş, G. İrez, O. Z. Yeşilel, O. Büyükgüngör, Z. Anorg. Allg. Chem. 2007, 633, 504-508. Reference 6 National committee for clinical laboratory standards (NCCLS) Performance standards for antimicrobial disk susceptibility tests. Approved standard (M2-A4). National committee for clinical laboratory standards Villanova, PA. 1990a. Reference 7 National committee for clinical laboratory standards. Methods for dilution antimicrobial susceptibility test for bacteria that grow aerobically. Approved standard (M7-A2). National committee for clinical laboratory standards, Villanova, PA. 1990b. Reference 8 Stoe&Cie, X-Area (Version 1.18) and X-Red32 (Version 1.04), Stoe&Cie. Darmstadt, Germany, 2002. Reference 9 M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. D. Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2005, 38, 381-388. Reference 10 Sheldrick G.M. SHELXL-97: Program for the Refinement of Crystal Structures. (Germany University of Göttingen), 1997. Reference 11 C.K. Johnson, M.N. Burnett, ORTEP-III (version 1.0.2), Rep. ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN (USA) (1996). Windows version: Farrugia L.J., University of Glasgow, Glasgow, Scotland (U.K.), 1997. Reference 12 L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838. Reference 13 Á. Somogyi, Medical applications of Mass Spectrometry, K. Vékey, A. Telekes and A. Vertes (editors) Elsevier B.V. 2008. Reference 14 L. Bajpai, M. Varshney, C. N. Seubert, S. M. J. Stevens, J. V. Johnson, R. A. Yost, D. M. Dennis, J. Am. Soc. Mass Spectrom. 2005, 16, 814-824. Reference 15 M. Taş, H. Batı, J. Chem. Res. 2006, 87-92. Reference 16 A. Zülfikaroğlu, M. Taş, H. Batı, B. Batı, Synth. React. Inorg.Met. Org. Chem. 2003, 33, 625-638. Reference 17 H. Batı, M. Taş, B. Batı, Synth. React. Inorg. Met. Org. Chem. 2001, 31, 541-548. Reference 18 H. Batı, M. Taş, M. Macit, Synth. React. Inorg. Met. Org.Chem. 1998, 28, 1371-1380. Reference 19 M. V. Barybin, P. L. Diaconescu, C. C. Cummins, Inorg. Chem. 2001, 40, 2892-2897. Reference 20 S. Sevagapandian, G. Rajagopal, K. Nehru, P. Athappan, Trans. Metal Chem. 2000, 25, 388-393. Reference 21 R. M. Srivastava, I. M. Brinn, J. O. Machura-Herrera, H. B. Faria, G. B. Carpenter, D. Andrade, C.G. Venkatesh, L. P. F. Morais, J. Mol. Struct. 1997, 406, 159-167. Reference 22 F. Karipçin, H. I. Uçan, I. Karataş, Trans. Metal Chem. 2002, 27, 813-817. Reference 23 M. Taş, H. Batı, J. Therm. Anal. Cal. 2006, 85, 295-299. Reference 24 B. K. Singh, U. K., Jetley, R. K., Sharma, B. S. Garg, Spectrochimica Acta Part A 2007, 68, 63-73. Reference 25 N. Tounsi, L. Dupont, A. Mohamadou, E. Guillon, M. Aplincourt, G. Rogez, Polyhedron 2008, 27, 674-3682. Reference 26 M. C. Fernández-Fernández, R. B. Calle, A. Macías, L. V. Matarranz, P. P. Lourido, Polyhedron 2008, 27, 2301-2308. Reference 27 F. Hamurcu, A. B. Gündüzalp, S. Çete S., B. Erk, Tran. Met. Chem. 2008, 33, 137-141.