Syntheses, Crystal Structures and Antibacterial Activities of Cobalt(Ⅱ) and Manganese(Ⅱ) Complexes with Schiff Base Ligand Derived from Tryptamine
刘超;牛俊峰;李阳;徐基贵;刘新华
a (School of Chemistry and Chemical Engineering,Suzhou University, Suzhou 234000, China)
b (School of Pharmacy, Anhui Medical University, Hefei 230000, China)
Syntheses, Crystal Structures and Antibacterial Activities of Cobalt(Ⅱ) and Manganese(Ⅱ) Complexes with Schiff Base Ligand Derived from Tryptamine
LIU Chao;NIU Jun-Feng;LI Yang;XU Ji-Gui;LIU Xin-Hua
a (School of Chemistry and Chemical Engineering,Suzhou University, Suzhou 234000, China)
b (School of Pharmacy, Anhui Medical University, Hefei 230000, China)
Two new mononuclear complexes, namely [Co(L)2] (1) and [Mn(L)2] (2) (HL = N-(3-methylsalicylidene)tryptamine), have been synthesized by the reactions of the ligand with cobalt acetate or manganese acetate in anhydrous ethanol. The crystal structures of the complexes were characterized by IR spectrum, elemental analysis, PXRD and single-crystal X-ray diffraction analysis. Complex 1 crystallizes in monoclinic, space group C2/c, with a = 23.146(2), b = 9.4864(10), c = 13.9261(15) Å, β = 102.898(2)°, V = 2980.6(5) Å3, Z = 4, Dc = 1.367 g/cm3, F(000) = 1284 and μ = 0.616 mm-1. Complex 2 crystallizes in monoclinic, space group P21/n, with a = 14.807(11), b = 13.118(10), c = 16.663(13) Å, β = 111.237(14)°, V = 3017(4) Å3, Z = 4, Dc = 1.342 g/cm3, F(000) = 1276 and μ = 0.477 mm-1. The units of complex 1 are linked by intermolecular N–H•••π hydrogen bonds into infinite 1D chains, which are further extended into a 3D supramolecular structure by a series of π•••π stacking interactions. The units of complex 2 are linked by intermolecular N–H•••π hydrogen bonds and C–H•••π hydrogen bonds into an infinite 3D supramolecular structure. Meanwhile, the antibacterial activities of the ligand and its complexes have been tested against four kinds of bacteria. The results show that the three compounds all have excellent antibacterial activities and that 1 and 2 possess stronger inhibiting effects against the bacteria than the Schiff base.
Two new mononuclear complexes, namely [Co(L)2] (1) and [Mn(L)2] (2) (HL = N-(3-methylsalicylidene)tryptamine), have been synthesized by the reactions of the ligand with cobalt acetate or manganese acetate in anhydrous ethanol. The crystal structures of the complexes were characterized by IR spectrum, elemental analysis, PXRD and single-crystal X-ray diffraction analysis. Complex 1 crystallizes in monoclinic, space group C2/c, with a = 23.146(2), b = 9.4864(10), c = 13.9261(15) Å, β = 102.898(2)°, V = 2980.6(5) Å3, Z = 4, Dc = 1.367 g/cm3, F(000) = 1284 and μ = 0.616 mm-1. Complex 2 crystallizes in monoclinic, space group P21/n, with a = 14.807(11), b = 13.118(10), c = 16.663(13) Å, β = 111.237(14)°, V = 3017(4) Å3, Z = 4, Dc = 1.342 g/cm3, F(000) = 1276 and μ = 0.477 mm-1. The units of complex 1 are linked by intermolecular N–H•••π hydrogen bonds into infinite 1D chains, which are further extended into a 3D supramolecular structure by a series of π•••π stacking interactions. The units of complex 2 are linked by intermolecular N–H•••π hydrogen bonds and C–H•••π hydrogen bonds into an infinite 3D supramolecular structure. Meanwhile, the antibacterial activities of the ligand and its complexes have been tested against four kinds of bacteria. The results show that the three compounds all have excellent antibacterial activities and that 1 and 2 possess stronger inhibiting effects against the bacteria than the Schiff base.
This project was supported by the National Natural Science Foundation of China (No. 21272008)
and the Natural Science Industry-University-Research Foundation of Suzhou University (2015hx014)
通讯作者:
刘超
E-mail: ahliuchao333@163.com
引用本文:
刘超;牛俊峰;李阳;徐基贵;刘新华. Syntheses, Crystal Structures and Antibacterial Activities of Cobalt(Ⅱ) and Manganese(Ⅱ) Complexes with Schiff Base Ligand Derived from Tryptamine[J]. 结构化学, 2016, 35(7): 1002-1010.
LIU Chao;NIU Jun-Feng;LI Yang;XU Ji-Gui;LIU Xin-Hua. Syntheses, Crystal Structures and Antibacterial Activities of Cobalt(Ⅱ) and Manganese(Ⅱ) Complexes with Schiff Base Ligand Derived from Tryptamine. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35(7): 1002-1010.
REFERENCES
(1) Feng, X.; Song, H. L.; Ye, B. X.; Huo, S. Z.; Xie, S. Y.; Guo, J. Z. Synthesis, crystal structure and electrochemistry properties of a cobalt(II) complex based on asymmetry Schiff base ligand. Chin. J. Struct. Chem. 2014, 33, 897–902.
(2) Bhattacharyya, A.; Sen, S.; Harms, K.; Chattopadhyay, S. Formation of three photoluminescent zinc(II) complexes with Zn2O2 cores: examples of bidentate bonding modes of potentially tri- and tetra-dentate Schiff bases. Polyhedron 2015, 88, 156–163.
(3) Hanif, M.; Chohan, Z. H. Synthesis, spectral characterization and biological studies of transition metal(II) complexes with triazole Schiff bases. Appl. Organomet. Chem. 2013, 27, 36–44.
(4) Gao, R.; Zhao, Y.; Jiang, D. Y.; Ding, G. H. Synthesis, structure and photophysical property of the Schiff base on N,N-ethylene-bis(3,5-dichlorosalicylideneimine) and its salen-Co(II) complex. Chin. J. Struct. Chem. 2015, 34, 741–748.
(5) Mahalakshmi, N.; Rajavel, R. Synthesis, spectroscopic, DNA cleavage and antibacterial activity of binuclear Schiff base complexes. Arab. J. Chem. 2014, 7, 509–517.
(6) Li, X.; Fang, C.; Zong, Z.; Cui, L. S.; Bi, C. F.; Fan, Y. H. Synthesis, characterization and anticancer activity of two ternary copper(II) Schiff base complexes. Inorg. Chim. Acta 2015, 432, 198–207.
(7) Sridhar, S. K.; Saravanan, M.; Ramesh, A. Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur. J. Med. Chem. 2001, 36, 615–625.
(8) Jia, L.; Shi, J.; Sun, Z. H.; Li, F. F.; Wang, Y.; Wu, W. N.; Wang, Q. Synthesis, crystal structure, DNA-binding properties, cytotoxic and antioxidation activities of several ternary copper(II) complexes with a new reduced Schiff base ligand. Inorg. Chim. Acta 2012, 391, 121–129.
(9) Hanif, M.; Chohan, Z. H. Synthesis, spectral characterization and biological studies of transition metal(II) complexes with triazole Schiff bases. Appl. Organomet. Chem. 2013, 27, 36–44.
(10) Qiu, X. Y.; Zhu, M. A.; Liu, Y.; Ding, X. Y.; Zhang, P. Synthesis, crystal structure and biological activity of a planar copper complex derived from s-benzyldithiocarbazate. Chin. J. Struct. Chem. 2010, 29, 1557–1561.
(11) Thamilarasan, V.; Jayamani, A.; Sengottuvelan, N. Synthesis, molecular structure, biological properties and molecular docking studies on MnII, CoII and ZnII complexes containing bipyridine-azide ligands. Eur. J. Med. Chem. 2015, 89, 266–278.
(12) Li, J. L.; Jiang, L.; Wang, B. W.; Tian, J. L.; Gu, W.; Liu, X.; Yan, S. P. Bio-relevant cobalt(II) complexes with compartmental polyquinoline ligand: synthesis, crystal structures and biological activities. J. Inorg. Biochem. 2015, 145c, 19–29.
(13) Kalita, M.; Tamuli, K. J.; Barman, P.; Sarma, B.; Baruah, R.; Boruah, H. P. D. Synthesis, crystal structure, bioactivities of Ni(II), Cu(II), Co(II) and Pd(Ⅱ) complexes with unsymmetrical thioether donor Schiff base: phosphine free Pd(II) complex catalyzed Suzuki reaction. Polyhedron 2015, 97, 140–147.
(14) Ekmekcioglu, P.; Karabocek, N.; Karabocek, S.; Emirik, M. Synthesis, structural and biochemical activity studies of a new hexadentate Schiff base ligand and its Cu(II), Ni(II), and Co(II) complexes. J. Mol. Struct. 2015, 1099, 189–196.
(15) Kumar, G.; Devi, S.; Johari, R.; Kumar, D. Synthesis, spectral characterization and antimicrobial evaluation of Schiff base Cr(III), Mn(III) and Fe(III) macrocyclic complexes. Eur. J. Med. Chem. 2012, 52, 269–274.
(16) Liu, C.; Zhuo, X.; Wu, Y. K.; Wang, L. Synthesis, characterization and crystal structure of a new Schiff base of tryptamine. Journal of Suzhou University 2011, 26, 60–62.
(17) Sheldrick, G. M. SADABS. Program for Empirical Absorption Correction of Area Detector. University of Göttingen, Germany 1996.
(18) Sheldrick, G. M. SHELXS-97, Program for the Crystal Structure Solution. University of Göttingen, Göttingen, Germany 1997.
(19) Sheldrick, G. M. SHELXL-97, Program for the Crystal Structure Refinement. University of Göttingen, Göttingen, Germany 1997.
(20) Back, D. F.; Hörner, M.; Broch, F.; Oliveira, G. M. D. Three-dimensional triazenido layers attained through classical and non-classical hydrogen interactions and its coordination to palladium under prolific occurrence of bifurcated hydrogen bonding. Polyhedron 2012, 31, 558–564.
(21) Tovar, L. G.; Ruiz, Á. D.; Wurst, K. Non-classical hydrogen bond (C–H∙∙∙I) directed self-assembly formation of a novel 1D supramolecular polymer, based on a copper complex [Cu{(CH3)2SO6]I4. Inorg. Chem. Commun. 2013, 32, 64–67.
(22) Chen, D. B.; Sheng, T. L.; Wang, X.; Chen, J. S.; Hu, S. M.; Fu, R. B.; Shen, C. J.; Zou, Q. Z.; Wu, X. T. Synthesis and crystal structure of a chiral manganese(Ⅲ) Schiff base complex. Chin. J. Struct. Chem. 2010, 29, 471–475.
(23) Cui, L.; Zhu, F. F.; Leong, C. F.; Ru, J.; Gao, F.; D’Alessandro, D. M.; Zuo, J. L. Cyanide-bridged single molecule magnet based on a manganese(III) complex with TTF-fused Schiff base ligand. Sci. China Chem. 2015, 58, 650–657.
2016, Vol. 35 
