Synthesis, Spectral Analysis and Antimicrobial Activity of New Pd (II) Complexes Involving 5,6-Dimethylbenzimidazole

doi:10.1007/s40242-023-2355-3

高等学校化学研究 ›› 2023, Vol. 39 ›› Issue (6): 968-975.doi: 10.1007/s40242-023-2355-3

Synthesis, Spectral Analysis and Antimicrobial Activity of New Pd (II) Complexes Involving 5,6-Dimethylbenzimidazole

Murat TÜRKYILMAZ, Murat DÖNMEZ, and Özlen ALTUN

Department of Chemistry, Trakya University, 22030 Edirne, Turkey

收稿日期:2022-12-21 出版日期:2023-12-01 发布日期:2023-11-18
通讯作者: Özlen ALTUN E-mail:ozlenaltun@yahoo.com
基金资助:
This work was supported by the Trakya University Research Fund (No.TUBAP- 2014-106).

Synthesis, Spectral Analysis and Antimicrobial Activity of New Pd (II) Complexes Involving 5,6-Dimethylbenzimidazole

Murat TÜRKYILMAZ, Murat DÖNMEZ, and Özlen ALTUN

Department of Chemistry, Trakya University, 22030 Edirne, Turkey

Received:2022-12-21 Online:2023-12-01 Published:2023-11-18
Contact: Özlen ALTUN E-mail:ozlenaltun@yahoo.com
Supported by:
This work was supported by the Trakya University Research Fund (No.TUBAP- 2014-106).

摘要/Abstract

摘要： In this study, firstly, 3-bromopropanenitrile (2a), ethyl bromoacetate (2b), and 2-bromoethan-1-amine (2c) were added to 5,6-dimethylbenzimidazole (1) and symmetrically- connected N-heterocyclic carbenes (NHC) [(3a-3c)] were synthesized. Then, the NHC precursor compounds were reacted with PdCl₂ and Pd (II)-NHC complexes [(4a—4c)] were obtained. The synthesized NHC precursors (3a-3c) and Pd (II)-NHC complexes (4a—4c) were characterized by different spectroscopic methods. The antibacterial activities of these products were measured against bacteria and fungus with the disc diffusion method. Pd (II)-NHC complexes had higher antibacterial activity than the NHC precursors. The synthesized compounds showed antimicrobial activity with different properties from each other. In vitro biological activities of salts and metal complexes on selected bacteria were determined by the broth dilution method based on Clinical and Laboratory Standards Institute guidelines. 1,3-Bis-(2-hydroxyethyl) imidazolinium bromide and 3-(2-ethoxy-2-oxoethyl)-1-(3- aminopropyl)-1H-imidazole-3-ium bromide had activity against Escherichia coli.

关键词: N-Heterocyclic carbene, Palladium (II)-NHC complex, Structural analysis, Antimicrobial activity

Abstract: In this study, firstly, 3-bromopropanenitrile (2a), ethyl bromoacetate (2b), and 2-bromoethan-1-amine (2c) were added to 5,6-dimethylbenzimidazole (1) and symmetrically- connected N-heterocyclic carbenes (NHC) [(3a-3c)] were synthesized. Then, the NHC precursor compounds were reacted with PdCl₂ and Pd (II)-NHC complexes [(4a—4c)] were obtained. The synthesized NHC precursors (3a-3c) and Pd (II)-NHC complexes (4a—4c) were characterized by different spectroscopic methods. The antibacterial activities of these products were measured against bacteria and fungus with the disc diffusion method. Pd (II)-NHC complexes had higher antibacterial activity than the NHC precursors. The synthesized compounds showed antimicrobial activity with different properties from each other. In vitro biological activities of salts and metal complexes on selected bacteria were determined by the broth dilution method based on Clinical and Laboratory Standards Institute guidelines. 1,3-Bis-(2-hydroxyethyl) imidazolinium bromide and 3-(2-ethoxy-2-oxoethyl)-1-(3- aminopropyl)-1H-imidazole-3-ium bromide had activity against Escherichia coli.

Key words: N-Heterocyclic carbene, Palladium (II)-NHC complex, Structural analysis, Antimicrobial activity

Murat TÜRKYILMAZ, Murat DÖNMEZ, and Özlen ALTUN. Synthesis, Spectral Analysis and Antimicrobial Activity of New Pd (II) Complexes Involving 5,6-Dimethylbenzimidazole[J]. 高等学校化学研究, 2023, 39(6): 968-975.

参考文献

[1] Glorius F., N-Heterocyclic Carbenes in Transition Metal Catalysis, SpringerVerlag, Berlin, 2006
[2] Wurtz S., Glorius F., Acc. Chem. Res., 2008, 41, 1523
[3] Hashmi A. S. K., Lothschuetz C., Graf K., Haeffner T., Schuster A., Rominger F., Adv. Synth. and Catal., 2011, 353(9), 1407
[4] Oehninger L., Rubbiani R., Ott I., Dalton Trans., 2013, 42(16), 3269
[5] Cisnetti F., Gibard C., Gautier A., J. Organomet. Chem., 2015, 782, 22
[6] Fortman G. C., Nolan S. P., Chem. Soc. Rev., 2011, 40(10), 5151
[7] Nemcsok D., Wichmann K., Frenking G., Organometallics, 2004, 23(15), 3640
[8] Gaillard S., Nun P., Slawin A. M. Z., Nolan S. P., Organometallics, 2010, 29(21), 5402
[9] Li W. S., Wang C. H., Ko S., Chang T. T., Jen Y. C., Yao C. F., More S. V., Jao S. C., Journal of Medicinal Chemistry, 2012, 55(4), 1583
[10] Peris E., Crabtree R. H., Coordination Chemistry Reviews, 2004, 248(21— 24), 2239
[11] Ray S., Mohan R., Singh J. K., Samantaray M. K., Shaikh M. M., Panda D., Ghosh P., J. Am. Chem. Soc., 2007, 129(48), 15042
[12] Kleinman E.F., The Bimolecular Aliphatic Mannich and Related Reactions in Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991
[13] Wang X., Su Q., Zhang Z., Yang J., Zhang Y., Zhang M., Chemical Communications, 2020, 56, 8460
[14] Fekri A., Keshk E. M., Khalil A.G. M., Taha I., Mol. Divers, 2022, 26, 781
[15] Scattolin T., Bortolamiol E., Palazzolo S., Caligiuri I., Perin T., Canzonieri V., Demitri N., Rizzolio F., Cavallo L., Dereli B., Mane M. V., Nolan S. P., Visentin F., Chem. Commun., 2020, 56, 12238
[16] Liu J., Zhou X., Rao H., Xiao F., Li C. J., Chemistry: A European Journal, 2011, 17(29), 7996
[17] Ofele K., Journal of Organometallic Chemistry, 1968, 12, 42
[18] Wanzlick H. W., Schönherr H. J., Angewandte Chemie International Edition, 1968, 7(2), 141
[19] Peris E., Chemical Reviews, 2018, 118(19), 9988
[20] Yang J., J. Coord. Chem., 2017, 70, 441
[21] Liang R. X., Jia Y. X., Acc. Chem. Res., 2022, 55(5), 734
[22] Ehrentraut A., Zapf A., Beller M., Synlett., 2000, 11, 1589
[23] Xiao J., Wang L., Zhang H., Ma N., Tao M., Zhang W., Chemical Engineering Science, 2022, 247(16), 117053
[24] Samiee S., Shiralinia A., Hoveizi E., Gable R. W., Inorganica Chimica Acta, 2022, 538, 120964
[25] Gu S., Chen C., Qiu H., Chen W., Current Organic Chemistry, 2011, 15, 3291
[26] Guisado-Barrios G., Hiller J., Peris E., Chem. Eur. J., 2013, 19, 10405
[27] Parmar D., Sugiono E., Raja S., Rueping M., Chem. Rev., 2014, 114, 9047
[28] Burrows A. D., Sci. Prog., 2002, 85, 199
[29] Crabtree R. H., New J. Chem., 2011, 35, 18
[30] Dahm G., Borre E., Guichard G., Bellemin-Laponnaz S., Eur. J. Inorg. Chem., 2015, 2015(10), 1665
[31] Simic D., Zaric M., Nikolic I., Zivkovic-Zaric R., Canovic P., Kocovic A., Radojevic I., Rakovic I., Jovicic S., Petrovic D., Stojkovic D., Vukovic N., Kacaniova M., Vukic M., Jevtic V., Dalton Transactions, 2022, 51, 1191
[32] Clinical and Laboratory Standards Institute, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, Approved standard— Second Edition, NCCLS Document M27-A2(ISBN 1-56238-469-4), Wayne, Pennsylvania, 2002
[33] Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Susceptibility Testing, Twenty-second Informational Supplement, CLSI Document M100-S22, Wayne, Pennsylvania, 2012
[34] Kaya E., Ozbilge H., Turk. J. Med. Sci., 2012, 42(2), 325
[35] Altun Ö., Koçer M. Ö., J. Mol. Struc., 2021, 1224(129242), 1
[36] Cajiao N., Mora H., Palencia M., Journal of Science with Technological Applications, 2016, 1(1), 77
[37] Cai W., Wang J., Chu C., Chen W., Wu C., Liu G., Advenced Science, 2018, 6(1), 1801526
[38] Ma S., Zhou Z., Ran G., Xie J., Luo X., Li Y., Wang L., Journal of Hazardous Materials, 2022, 422, 126785
[39] Geary W. J., Coord. Chem. Rev., 1971, 7(1), 81
[40] Kettle S. F. A., Coordination Compounds, Thomas Nelson and Sons, London, 1975
[41] Dyer J. R., Application of Absorption Spectroscopy of Organic Compounds, Prentice-Hall, New Jersey, 1965
[42] Lever A. B. P., Inorganic Electronic Spectroscopy, Elsevier, New York, 1984
[43] Kang J. G., Cho D. H., Park C., Kang S. K., Kim I. T., Lee S. W., Lee H. H., Lee Y. N., Lim D. W., Lee S. J., Kim S. H., Bae Y. J., Bull. Korean Chem. Soc., 2008, 29(3), 599
[44] Jambi S. M. S., Kandil S. S., J. Mater. Environ. Sci., 2012, 3(3), 591
[45] Lambert J. B., Shurwell H. F., Verbit L., Cooks R. G., Stout G. H., Organic Structural Analysis, MacMillan, New York, 1976
[46] Nakamato K., Infrared and Raman Spectra of Inorganic and Coordination Compounds, John Wiley and Sons, New York, 1997
[47] Socrates G., Infrared Characterization Group Frequencies: Tables and Charts, 3rd Edition, John Wiley and Sons, London, 2004
[48] Giovagnini L., Ronconi L., Aldinucci D., Lorenzon D., Sitran S., Fregona D., J. Med. Chem., 2005, 48(5), 1588
[49] Salem M. A., Bakr E. A., El-Attar H. G., Spectrochim. Acta, Part A, 2018, 188, 155
[50] Warren B. E., X-Ray Diffraction, Dover, New York, 1990
[51] Barbosa H. F. G., Attjioui M., Ferreira A. P. G., Dockal E. R., El Gueddari N. E., Moerschbacher B. M., Cavalheiro E. T. G., Molecules, 2017, 22(1987), 1
[52] Kavitha K., Reddy L., Arab. J. Chem., 2016, 9(5), 640
[53] Yılmaz V. T., Ertem A., Guney E., Buyukgungor O., Z. Anorg. Allg. Chem., 2010, 636(3/4), 610
[54] Maskovic J. M., Maskovic P. Z., Koval’chuk T. V., Loginova N. V., Trifunovic S. R., Der Chemica Sinica, 2018, 9(1), 535
[55] Al-Hamdani A. A. S., Balkhı A. M., Falah A., Shaker S. A., J. Chil. Chem. Soc., 2015, 60(1), 2774
[56] Pahontu E., Paraschivescu C., Ilies D. C., Poirier D., Oprean C., Paunescu V., Gulea A., Rosu T., Bratu O., Molecules, 2016, 21(5), 1
[57] Kumar V. A., Sarala Y., Siddikha A., Vanitha S., Babu S., Reddy A. V., J. Appl. Pharm. Sci., 2018, 8(4), 071
[58] Mihalache M., Negreanu-Pirjol T., Dumitraşcu F., Draghici C., Calinescu M., J. Serb. Chem. Soc., 2018, 83(3), 271

Synthesis, Spectral Analysis and Antimicrobial Activity of New Pd (II) Complexes Involving 5,6-Dimethylbenzimidazole

Synthesis, Spectral Analysis and Antimicrobial Activity of New Pd (II) Complexes Involving 5,6-Dimethylbenzimidazole

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 6

编辑推荐

Metrics

本文评价

[1]	YAN Liuqing, FU Jiaxu, LI Shuang, ZHANG Jinlong, WANG Shuang, GU Qiang, ZHANG Yumin, LIN Feng. Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl[J]. 高等学校化学研究, 2021, 37(3): 639-646.
[2]	FENG Fan, LI Jing, ZHANG Zhihui, FU Jiaxu, ZHANG Yumin, GU Qiang. Design, Ultrasonic-assisted Synthesis and Evaluation In vitro Antimicrobial Activity of Bis-isoxazole Derivatives Bearing Chloro-pyridinyl Group[J]. 高等学校化学研究, 2021, 37(3): 668-673.
[3]	GENG Guoliang, MA Xiaofei, GENG Hongbin, WU Yiyong. Effect of Thermal Cycles on the Thermal Expansion Behavior of T700 Carbon Fiber Bundles[J]. 高等学校化学研究, 2018, 34(3): 451-456.
[4]	HU Xi-yu, CHEN Bing-nian, WANG Li, CHEN Fa-he. Inhibition of α/β-K₆P₂W₁₈O₆₂·10H₂O on the Activity of Mushroom Tyrosinase and Its Antimicrobial Effects[J]. 高等学校化学研究, 2012, 28(5): 862-865 .
[5]	CHEN Feng-ying, WU Wang-ting, LI Heng-xin, HE Shui-yang, WEN Zhen-yi, LI Jia-xing. Molecular Structure and Properties of a Novel Acylhydrazone (C₁₄H₁₄O₆N₄)·HCON(CH₃)₂·2H₂O[J]. 高等学校化学研究, 2012, 28(3): 524-528.
[6]	WU Ming-jiang, JIANG De-zhi, LIU Tie-mei, ZHANG Li-ping. Structural Analysis of Water-soluble Polysaccharide PIP₁ Extracted from the Cultured Mycelium of Phellinus igniarius[J]. 高等学校化学研究, 2006, 22(6): 708-711.