Citation: Abdalla M Khedr, Mohamed Gaber, Khalil M Saad-allah. Synthesis, Characterization and Antimicrobial Efficiency of Some Zirconyl(Ⅱ) Complexes Involving O, N-Donor Environment of Triazole-Based Azodyes[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(5): 1201-1211. doi: 10.11862/CJIC.2014.150 shu

Synthesis, Characterization and Antimicrobial Efficiency of Some Zirconyl(Ⅱ) Complexes Involving O, N-Donor Environment of Triazole-Based Azodyes

1.
1 Chemistry Department, Faculty of Science, Tanta University, Tanta 31111, Egypt;

Received Date: 25 October 2013
Available Online: 2 January 2014

Nine zirconyl(Ⅱ) complexes of 3-(2-hydroxynaph-1-ylazo)-1,2,4-triazole (HL¹), 3-(2,4-dihydroxyphen-1-ylazo)-1,2,4-triazole (HL²), 3-(2-hydroxy-3-carboxynaph-1-ylazo)-1,2,4-triazole (HL³), 3-(2-hydroxy-5-bromophen-1-ylazo)-1,2,4-triazole (HL⁴) and 3-(2-hydroxy-5-methylphen-1-ylazo)-1,2,4-triazole (HL⁵) have been synthesized and characterized by elemental analysis, molar conductance, magnetic moment and spectroscopic data (IR, electronic and ¹H-NMR) as well as thermal analyses (TGAand DTA). The results show that HL¹-HL⁵ coordinate to zirconyl(Ⅱ) ions as bidentate monobasic ligands through the azo nitrogen and the oxygen of hydroxyl group yielding mononuclear complexes. The biological activity of the ligands and their complexes were studied on four Gram-negative bacteria Escherichia coli, Serratia marcescens, Enterobacter cloacae and Proteus vulgaris and two Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus as well as two fungi Candida albicans and Aspergillus niger. The minimum inhibitory concentrations (MICs) of the prepared compounds were determined by agar diffusion assay using filter paper disc diffusion method. In most cases, metallization increases the antimicrobial activity compared with the free ligand.
- Coordination modes;biological activity;Zirconyl complexes;triazole azodyes;spectral and thermal studies
1. [1]
  [1] Ispir E. Dyes Pigm., 2009, 82:13-19
2. [2]
  [2] Nejati K, Rezvani Z, Massoumi B. Dyes Pigm., 2007, 75:653-657
3. [3]
  [3] Guleman N N, Rollas S, Erdeniz H, et al. J. Pharm. Sci., 2001, 26:1-12
4. [4]
  [4] Awad I M A. Phosphorus, Sulfur Silicon Relat. Elem., 1996, 114:17-28
5. [5]
  [5] Khedr A M. Chem. Anal. (Warsaw), 2009, 54:783-793
6. [6]
  [6] Khedr A M, Gaber M. Inorg. Chem. (Ind. J.), 2008, 3:175-181
7. [7]
  [7] Khedr A M. Chem. Pap.-Chem. Zvesti, 2008, 60:541-546
8. [8]
  [8] Gaber M, Hassanien A M, Rehab A F, et al. Egypt. J. Chem., 2006, 3:431-438
9. [9]
  [9] Khedr A M, Gaber M. Spectrosc. Lett., 2005, 38:431-445
10. [10]
  [10] Khedr A M, Gaber M, Issa R M, et al. Dyes Pigm., 2005, 67: 117-126
11. [11]
  [11] Amin A S, Mohammed T Y, Mousa A A. Spectrchim. Acta A, 2003, 59:2577-2584
12. [12]
  [12] Vicente S, Manisso N, Queiroz Z F, et al. Talanta, 2002, 57: 475-480
13. [13]
  [13] Karpinska J, Kulikowska M. J. Pharm. Biomed. Anal., 2002, 29:153-158
14. [14]
  [14] Li Z, Pan J, Tang X. Anal. Biomed. Chem., 2002, 374: 1125-1131
15. [15]
  [15] Zaporozhets O, Petruniock N, Bessarabova O, et al. Talanta, 1999, 49:899-906
16. [16]
  [16] Visser A E, Swatloski R P, Griffin S T, et al. Spec. Sci. Technol., 2001, 36:785-804
17. [17]
  [17] Lee W, Lee S E, Lee C H, et al. Microchem. J., 2001, 70: 195-203
18. [18]
  [18] Chen J, Teo K C. Anal. Chem. Acta, 2001, 434:325-330
19. [19]
  [19] Karipcin F, Dede B, Percin S, et al. Dyes Pigm., 2009, 84: 14-18
20. [20]
  [20] Cheng Y, Zhang M, Yang H, et al. Dyes Pigm., 2008, 76: 775-783
21. [21]
  [21] Nashihara H. Coord. Chem. Rev., 2005, 249:1468-1473
22. [22]
  [22] Muraoka T, Kinbara K, Kobayashi Y, et al. J. Am. Chem. Soc., 2003, 125:5612-5613
23. [23]
  [23] Natansohn A, Rochon P. Chem. Rev., 2002, 102:4139-4175
24. [24]
  [24] Khedr A M, Gaber M, Abd El-Zaher E H. Chin. J. Chem., 2011, 29:1124-1132
25. [25]
  [25] Al-Soud Y A, Al-Dweri M N, Al-Masoudi N A. Il Farmaco, 2004, 59:775-783
26. [26]
  [26] Turan-Zitouni G, Kaplanckh Z A, Yldz M T, et al. Eur. J. Med. Chem., 2005, 40:607-613
27. [27]
  [27] Jalilian A R, Sattari S, Bineshmarvasti M, et al. Arch. Pharm., 2000, 333:347-354
28. [28]
  [28] Bagihalli G B, Avaji P G, Patil S A, et al. Eur. J. Med. Chem., 2008, 43:2639-2649
29. [29]
  [29] Holla B S, Veeredra B, Shivanda M K, et al. Eur. J. Med. Chem., 2003, 38:759-764
30. [30]
  [30] Kapalcikli Z A, Zitoungi G T, Ozdemir A, et al. Eur. J. Med. Chem., 2008, 43:155-159
31. [31]
  [31] Pomarnacka E, Kedra I K. Il Farmaco, 2003, 58:423-429
32. [32]
  [32] Tozkoparan B, Kupeli E, Yeilada E, et al. Bioorg. Med. Chem., 2007, 15:1808-1814
33. [33]
  [33] Labanauskas L, Udrenaite E, Gaidelis P, et al. Il Farmaco, 2004, 59:255-259
34. [34]
  [34] Zahajska L, Klimesova V, Koci J, et al. Arch. Pharm., 2004, 337:549-555
35. [35]
  [35] Foroumadi A, Mansouri S, Kiani Z, et al. Eur. J. Med. Chem., 2003, 38:851-854
36. [36]
  [36] Badr S M, Barwa R M. Bioorg. Med. Chem., 2011, 19:4506-4512
37. [37]
  [37] Singh K, Barwa M S, Tyagi P. Eur. J. Med. Chem., 2006, 41: 147-153
38. [38]
  [38] Bhat K S, Poojary B, Prasad D J, et al. Eur. J. Med. Chem., 2009, 44:5066-5070
39. [39]
  [39] Li Z, Gu Z, Yin K, et al. Eur. J. Med. Chem., 2009, 44: 4716-4720
40. [40]
  [40] Banerjee P, Pandey O P, Sengupta S K. Transition Met. Chem., 2008, 33:1047-1052
41. [41]
  [41] Ghassemzadeh M, Fallahnedjad L, Heravi M M, et al. Polyhedron, 2008, 27:1655-1664
42. [42]
  [42] enery S, Era A, entürk O S, et al. J. Coord. Chem., 2008, 61: 740-749
43. [43]
  [43] Bekircan O, Byklolu Z, Acar I, et al. J. Organomet. Chem., 2008, 693:3425-3429
44. [44]
  [44] Gaber M, El-Baradie K Y, El-SAyed Y S Y. Spectrochim. Acta A, 2008, 69:534-541
45. [45]
  [45] Gaber M, Hassanein A M, Lotfalla A A. J. Mol. Struct., 2008, 875:322-334
46. [46]
  [46] Gaber M, Mansour I A, El-SAyed Y S Y. Spectrochim. Acta A, 2007, 68:305-311
47. [47]
  [47] Gaber M, Fayed T A, El-Daly S, et al. Spectrochim. Acta A, 2007, 68:169-175
48. [48]
  [48] Khedr A M. Chem. Pap.-Chem. Zvesti, 2006, 60:138-142
49. [49]
  [49] Gaber M, Ayad M M, El-SAyed Y S Y. Spectrochim. Acta A, 2005, 62:694-702
50. [50]
  [50] Khedr A M. Egypt. J. Anal. Chem., 2005, 14:100-116
51. [51]
  [51] EL-Baradie K Y, Issa R M, Gaber M. Ind. J. Chem., 2004, 43:1126-1130
52. [52]
  [52] Patel H S, Oza K K. E-J. Chem., 2009, 6:371-376
53. [53]
  [53] Gaber M, Hassanein M, Ahmed H A. Ind. J. Tex. Res., 1986, 11:48-53
54. [54]
  [54] Carcelli M, Ianelli S, Pelogatti P, et al. Inorg. Chim. Acta, 2005, 358:903-911
55. [55]
  [55] Pridham T G, Lindenfelser L A, Shotwell O L, et al. Phytopathology, 1956, 46:568-575
56. [56]
  [56] Collee G J, Duguid J P, Farser A G, et al. Practical Medical Microbiology. New York:Churchill Livingstone, 1989.
57. [57]
  [57] Hsueh P R, Chang J C, Teng L J, et al. J. Clin. Microbiol., 1997, 35:1021-1023
58. [58]
  [58] Tas E, Aslanoglu M, Kilic A, et al. J. Chem. Res.(s), 2006: 242-245
59. [59]
  [59] El-Tabl A S, El-Saied F A, Al-Hakimi A N. Transition Met. Chem., 2007, 32:689-701
60. [60]
  [60] El-Tabl A S. Transition Met. Chem., 1997, 22:400-412
61. [61]
  [61] Maurya R C, Patel P. Spectrosc. Lett., 1999, 32:213-236
62. [62]
  [62] El-Wakeil N, Khedr A M, Mansour R. Chin. J. Chem., 2010, 28:463-470
63. [63]
  [63] Yadava H D S, Senguptya S K, Tripathi S C. Inorg. Chem. Acta, 1987, 128:1-6
64. [64]
  [64] Cukuravali A, Yilmaz I, Kirbag S. Transition Met. Chem., 2006, 31:207-214
65. [65]
  [65] Dash D C, Mahapatra A, Naik P, et al. J. Korean Chem. Soc., 2011, 55:412-423
66. [66]
  [66] Khedr A M, Draz D F. J. Coord. Chem., 2010, 63:1418-1429
67. [67]
  [67] Chaudhry S C, Verma C, Bhatt S S, et al. Synth. React. Inorg. Met.-Org. Chem., 2004, 34:1031-1042
68. [68]
  [68] Badea M, Emandi A, Marinescu D, et al. J. Therm. Anal. Calorim., 2003, 72:525-531
69. [69]
  [69] House J E. Thermochim. Acta, 1980, 40:225-336
70. [70]
  [70] Azizi N, Saidi M R. Tetrahedron, 2003, 59:5329-5332
71. [71]
  [71] Palaska E, Sahin G, Kelicen P, et al. Il Farmaco, 2002, 57: 101-107
72. [72]
  [72] Srivastava R S. Inorg. Chim. Acta, 1981, 56:165-168
1. [1]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
2. [2]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
3. [3]
  Wenke ZHENG , Ce LIU , Wei CHEN , Hongshan KE , Fanlong ZENG , Yibo LEI , Anyang LI , Wenyuan WANG . Synthesis and bonding analysis of low-coordinate Fe and Cr complexes with ultra-bulky silylamino groups. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1285-1293. doi: 10.11862/CJIC.20250095
4. [4]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
5. [5]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
6. [6]
  Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105
7. [7]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
8. [8]
  Chengyan XU , Jiangnan YU , Yu LI , Xizhen PAN , Yinlin HOU , Wenmin WANG . Synthesis, structure, and bioactivity of a Ho₄ complex bridged by azide group. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1453-1462. doi: 10.11862/CJIC.20260033
9. [9]
  Jinrong Bao , Jinglin Zhang , Wenxian Li , Xiaowei Zhu . 苯甲酸稀土配合物的制备及性能表征——基于应用化学专业人才培养的综合化学实验案例分析. University Chemistry, 2025, 40(8): 218-224. doi: 10.12461/PKU.DXHX202409142
10. [10]
  Zhenzhen Xue , Lixing Zhao , Jie Pan , Jixiang Hu . 配位化合物教学中的教研结合探索. University Chemistry, 2026, 41(9): 101-106. doi: 10.12461/PKU.DXHX202509020
11. [11]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
12. [12]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
13. [13]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
14. [14]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
15. [15]
  Jiaqi Chen , Liang Chen , Xiaocui Wei , Yankai Wang , Yahui Chang , Xinghao Ji , Haoyu Yang , Yue Sun , Yawen Wang , Xiufeng Shi , Xu Wu . Digital Empowerment for Foundational Excellence: A Digitally Enhanced Coordination Titration Experiment of Heating Pack Component Analysis. University Chemistry, 2026, 41(1): 382-393. doi: 10.12461/PKU.DXHX202506008
16. [16]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
17. [17]
  Jinyang SUI , Zhonghao NIU , Hao XU , Jingli XIE . Zinc(Ⅱ) coordination polymers from mixed triazole and carboxylate ligands: Synthesis and properties for CO₂ cycloaddition and photocatalytic dye degradation. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1603-1612. doi: 10.11862/CJIC.20260089
18. [18]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
19. [19]
  Yang ZHOU , Lili YAN , Wenjuan ZHANG , Pinhua RAO . Thermal regeneration of biogas residue biochar and the ammonia nitrogen adsorption properties. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1574-1588. doi: 10.11862/CJIC.20250032
20. [20]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1099)
HTML views(50)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142