Synthesis, Characterization, Antibacterial, Antioxidant Studies of New 2-(5-(2-((1E,2E)-3- (2-methoxyphenyl)allylidene)hydrazinyl)-1,3,4- oxadiazol-2-yl)Phenol with the Some Transition Metalions
DOI:
https://doi.org/10.61841/3z7pmp12Keywords:
Ligand, Complexes, Characterization, Electrostatic Potential, AntibacterialAbstract
A new ligand,, 2-(5-(2-((1E,2E) -3-(2-methoxyphenyl)allylidene)hydrazinyl) -1,3,4-oxadiazol-2-yl)phenol and its complexes with Cr(ІІІ), Co(ІІ), Ni(ІІ), and Cu(ІІ) ions were synthesized. The new ligand and its complexes have been characterized on the basis of their spectra of H1NMR, mass, Fourier transform infrared (FTIR), as well as magnetic susceptibility, elemental analysis (CHN), and conductance measurements. The program of HyperChem 8 has been used for theoretical accounts using the PM3 method to study the electrostatic potential that provided good information about the complexity site. Of the result obtained, we can suggest octahedral geometries for Cr(ІІІ), tetrahedral geometry for Co(ІІІ), and square planar geometry for Ni(ІІ) and Cu(ІІ). The antioxidant activity of the ligand was evaluated by DPPH scavenging, and the ligand showed high antioxidant activity. The ligand and its complex gave good activity antibacterial.
Downloads
References
[1] C. S. De Oliveira, B. F. Lira, J. M. Barbosa-Filho, J. G. F. Lorenzo and P. F. De Athayde-Fiho, "synthetic
approaches and pharmacological activity of 1,3,4-oxadiazoles: A review of the literature from 2000-2012,"
Molecules, 17(12), 10192-10231, 2012.
[2] S. M. Zachariah, M. Ramkumar, N. George, M. S. Ashif, and M. April, “Sciences A Review on
Oxadiazole,” Res. J. Pharm. Biol. Chem. Sci., vol. 6, no. 2, pp. 205–219, 2015.
[3] A. Pangal and J. A. Shaikh, "Various Pharmacological aspects of 2, 5-Disubstituted 1,3,4-Oxadiazole
Derivatives: A Review," Res. J. Chem. Sci. 3(12), 79-89, 2013.
[4] P. W. Lei, Z. Jian, and Z. H. Fang, “Potent antibacterial agents: pyridinium-functionalized amphiphiles
bearing 1, 3, 4-oxadiazole scaffolds,” Springer-Online, 2016.
[5] I.A.Flifel, A. H.Gatea, S.A.ali, “Synthesis, Characterization, Antimicrobial New 2,2'-[(1E,2E)-ethane-1,2-diylidenedi(2E)hydrazin-1-yl-2-ylidene]bis(5-methyl-1,3,4-oxadiazole) and their transition.” J. Thi-Qar sci. 6, 1991-8690, 2017.
[6] T. Zhang et al., “Antibacterial and Antifungal Activities of 2- (substituted ether) -5- ( 1- phenyl-5- ( tri fl u uoromethyl ) -1 H -pyrazol-4-yl ) -1, 3,4-oxadiazole Derivatives,” Wiley Period., pp. 4–10, 2017.
[7] V. B. Iyer, B. M. Gurupadayya, K. V. Sairam, B. Inturi, R. S. Chandan, and A. K. Tengli, “AntiInflammatory Activity of 1,3,4-Oxadiazoles Derived from Benzoxazole,” J. Pharm. Sci. Pharmacol., vol.
2, no. 3, pp. 233–241, 2015.
[8] M. Agarwal, V. Singh, S. K. Sharma, P. Sharma, Md. Y. Ansari, S. S. Jadav, S. Yasmin, R. Sreenivasulu,
M. Z. Hassan, V. Saini & M. Jawed, "Design and synthesis of new 2,5-disubstituted-1,3,4-oxadiazole
analogues as anticancer agents", Medicinal Chemistry Research, 25(10), 2289–2303, 2016.
[9] N. Siddiqui, J. Akhtar, and M. S. Yar, “Substituted phenyl containing 1,3,4-oxadiazole-2-yl-but-2-
enamides: synthesis and preliminary evaluation as promising anticonvulsants”, Med. Chem. Res., 23(11).
2014.
[10] L. Dong, B. Song, J. Wu, Z. Wu, Y. Zhu, and D. Hu, “Synthesis and antiviral activity of novel thioether
derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties,” Phosphorus. Sulfur. Silicon
Relat. Elem., vol. 191, no. 6, pp. 904–907, 2016.
[11] Z. Hajimahdi, A. Zarghi, R. Zabihollahi, and M. R. Aghasadeghi, “Synthesis, biological evaluation, and
molecular modeling studies of new 1,3,4-oxadiazole- and 1,3,4-thiadiazole-substituted 4-oxo-4Hpyrido[1,2-a]pyrimidines as anti-HIV-1 agents,” med. Chem. Res., 22(5), 2467-2475, 2012.
[12] R. V Shingalapur, K. M. Hosamani, R. S. Keri, and M. H. Hugar, “European Journal of Medicinal
Chemistry Derivatives of benzimidazole pharmacophore : Synthesis, anticonvulsant, antidiabetic and DNA
cleavage studies,” Eur. J. Med. Chem., vol. 45, no. 5, pp. 1753–1759, 2010.
[13] N. C. D. A. R. Trivedi and H. V. V. H. C. Somani, “Synthesis and biological evaluation of 1, 3, 4-
oxadiazole bearing dihydropyrimidines as potential antitubercular agents,” Med. Chem. Res., vol. 2, no. 25,
pp. 329–338, 2015.
[14] S. J. Gilani, S. A. Khan, and N. Siddiqui, “Bioorganic & Medicinal Chemistry Letters Synthesis and
pharmacological evaluation of condensed heterocyclic derivatives of isoniazid,” Bioorg. Med. Chem. Lett.,
vol. 20, no. 16, pp. 4762–4765, 2010.
[15] G. Chawla, B. Naaz, A. A. Siddiqui, “Exploring 1, 3, 4-Oxadiazole Scaffold For Anti-inflammatory And
Analgesic Activities: A Review Of Literature From 2005-2016,” Mini Reviews in Medicinal Chemistry,
18(3), 216-233, 2018.
[16] N. Renuka, H. K. Vivek, G. Pavithra, and K. A. Kumar, “Synthesis of Coumarin Appended Pyrazolyl-
1,3,4-Oxadiazoles and Pyrazolyl-1,3,4-Thiadiazoles: Evaluation of Their In Vitro Antimicrobial and
Antioxidant Activities and Molecular Docking Studies,” Russ. J. Bioorganic Chem., vol. 43, no. 2, pp.
197–210, 2017.
[17] M. Bouanis, M. Tourabi, A. Nyassi, A. Zarrouk, C. Jama, and F. Bentiss, “Corrosion inhibition
performance of 2,5-bis(4-dimethylaminophenyl)-1,3,4-oxadiazole for carbon steel in HCl solution:
Gravimetric, electrochemical and XPS studies,” Applied Surface Science, vol. 389. Elsevier B.V., pp. 952–
966, 2016.
[18] G. Zhou, Y. Cheng, L. Wang, X. Jing and F. Wang, Novel polyphenylenes containing phenol-substituted
oxadiazole moieties as fluorescent chemosensors for fluoride ion”, Macromolecules, 38(6), 2148-2153,
2005.
[19] K. Hunger, Industrial Dyes Chemistry, Properties, Applications. Wiley-VCH, 2003.
[20] C. Anghel, M. Matache, C. C. Paraschivescu, A. M. Madalan, and M. Andruh, “A novel 1-D coordination
polymer constructed from disilver-1,3,4-oxadiazole nodes and perchlorato bridges Catalin,” ElsevierInorganic Chem. Commun., vol. 76, pp. 22–25, 2017.
[21] N. Deshapande, N. S. Belavagi, S. I. Panchamukhi, M. Hussain, I. Ahmed, and M. Khazi, “Synthesis and
optoelectronic properties of thieno[2,3-b]thiophene based bis 1,3,4-oxadiazole derivatives as blue
fluorescent material for use in organic light emitting diodes,” ElsOPTICAL Mater., 37(2), 516–519, 2014.
[22] Dina A. Najeeb, “Some Transition Metal Complexes with 2-thioacetic acid-5-pyridyl- 1,3,4-oxadiazol,” J.
Al-Nahrain Univ., vol. 14, no. 3, pp. 35–39, 2011.
[23] K. Kishore, A. Samad, Y. Kumar, M. Shaharyar, R. L. Khosa, J. Jain, V. Kumar, Priyanka Singh,
“European Journal of Medicinal Chemistry Design, synthesis and biological evaluation of 1, 3, 4-
oxadiazole derivatives,” Eur. J. Med. Chem., vol. 45, no. 11, pp. 4963–4967, 2010.
[24] P. Derivatives, M. T. Abdel-aal, W. A. El-sayed, S. M. El-kosy, and E. S. H. El-ashry, “Synthesis and
Antiviral Evaluation of Novel 5-(N-Aryl- aminomethyl-1,3,4-oxadiazol-2-yl)hydrazines and Their Sugars,
1,2,4-Triazoles, Tetrazoles and Pyrazolyl Derivatives,” Arch. Pharm. Chem. Life Sci, vol. 341, pp. 307–
313, 2008.
[25] M. S. Yadawe, S. N. Unki, and S. A. Patil, “Synthesis, Spectral Characterization and Biological Studies of
Lanthanum ( III ) Complexes with Schiff Bases,” Int. Lett. Chem. Phys. Astron., vol. 12, pp. 94–104, 2013.
[26] H. A. Mohamad, B. Mohamad, and H. Ameem, “Synthesis and Characterization of Co(II), Ni(II) and
Cu(II) Complexes with Thio-1,3,4-oxadiazole Derivatives,” Cryst. Ideas–The Role Chem. Springer Int.
Publ., pp. 253–266, 2016.
[27] S. Menati, H. Amiri, B. Askari, M. Riahi, F. Jalilian, and G. Dini, “Synthesis and characterization of
insoluble cobalt(II), nickel(II), zinc(II) and palladium(II) Schiff base complexes: Heterogeneous catalysts
for oxidation of sulfides with hydrogen peroxide,” Comptes rendus - Chim.,pp.1-10, 2015.
[28] N. Nazarbahjat, A. Ariffin, Z. Abdullah, M. A. Abdulla, J. K. S. Shia, K. H. Leong, "Synthesis,
characterization, drug-likeness properties and determination of the in vitro antioxidant and cytotoxic
activities of new 1,3,4-oxadiazole derivatives", Med. Chem. Res., 25(9), 2015-2029, 2016.
[29] D.. A. T. Gary.L.Miessler, “Inorganic chemistry” 2nd Ed. pearson prentice hall, Upper Saddle River, NJ,
1991.
[30] R. M. Shakir, A. Ariffin and M. A. Abdulla, "Synthesis of New 2,5-Di-substituted 1,3,4-Oxadiazoles
Bearing 2,6-Di-tert-butylphenol Moieties and Evaluation of Their Antioxidant Activity", Molecules, 19(3),
3436-3449, 2014.
[31] N. Nazarbahjat, F. A. Kadir, A. Ariffin, M. A. Abdulla, Z. Abdullah, & W. A. Yehye, "Antioxidant
Properties and Gastroprotective Effects of 2-(Ethylthio)Benzohydrazones on Ethanol-Induced Acute
Gastric Mucosal Lesions in Rats", PLOS ONE., 11(6), 1-21, 2016.
[32] I. Ahmad, and A. Z. Beg, "Antimicrobial and photochemical studies on 45 Indian medicinal plants against
multi-drug resistant human pathogens" Ethnopharmacology J., 74(2), 113-123, 2001.
[33] R. Hout,W. J. Pietro and W. J. Herhre, A pictorial Approach to Molecular Structure and Reactivity, John
Wiley, New York, 1, (1984).
Downloads
Published
Issue
Section
License
Copyright (c) 2020 AUTHOR

This work is licensed under a Creative Commons Attribution 4.0 International License.
You are free to:
- Share — copy and redistribute the material in any medium or format for any purpose, even commercially.
- Adapt — remix, transform, and build upon the material for any purpose, even commercially.
- The licensor cannot revoke these freedoms as long as you follow the license terms.
Under the following terms:
- Attribution — You must give appropriate credit , provide a link to the license, and indicate if changes were made . You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
- No additional restrictions — You may not apply legal terms or technological measures that legally restrict others from doing anything the license permits.
Notices:
You do not have to comply with the license for elements of the material in the public domain or where your use is permitted by an applicable exception or limitation .
No warranties are given. The license may not give you all of the permissions necessary for your intended use. For example, other rights such as publicity, privacy, or moral rights may limit how you use the material.