Synthesis, Characterizatiᴏn, and Bioactivity Assessment of Rh(III) and VO(IV) Complexes with Isatin Derivative N1,N2-bis(2-oxoindolin-3-ylidene)ethanebis(thioamide)

https://doi.org/10.22146/ijc.91731

Yusra Jalil Ahmed(1*), Shurooq Abdulfattah Hasan(2), Waeel Mohammed Hamud(3), Nawal Hamdan Mahmoud(4)

(1) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10052, Iraq
(2) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10052, Iraq
(3) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10052, Iraq
(4) Department of Physics, College of Science, Mustansiriyah University, Baghdad 10052, Iraq
(*) Corresponding Author

Abstract


The new two-component complexes of Rh(III) as well as VO(IV), with the base of Schiff ligand associated with the isatin derivative N1,N2-bis(2-oxoindolin-3-ylidene)ethanebis(thioamide) (L) were prepared by one-step method reaction between isatin compound and dithiooxamide by condensation in presence of glacial acetic acid and investigated through applying the FTIR, UV-vis devices, evaluation of carbon, hydrogen, nitrogen and halogens elements using elemental analysis, flame atomic absorption, magnetic susceptibility, molar conductivity, GC-MS, LC-MS, XRD, 1H and 13C-NMR. Depending on the results obtained from the measurement techniques, the structure of Rh(III) complex was octahedral geometry, while VO(IV) complex was square pyramidal geometry. The antibacterial property for the prepared Schiff-based ligand L and metallic complexes 1 and 2 in this research was examined towards two different kinds about pathological microbes growth of Escherichia coli and Staphylococcus aureus, respectively, in comparison with conventional antibiotic cephalexin.


Keywords


azomethine ligand; thioamide derivative; rhodium(III) complex; oxovanadium(IV) complex; X-ray diffraction

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References

[1] Lahari, K., and Sundararajan, R., 2020, Design and synthesis of novel isatin derivatives as potent analgesic, anti-inflammatory and antimicrobial agents, J. Chem. Sci., 132 (1), 94.

[2] Dantas, L.L.S.F.R., Fonseca, A.G., Pereira, J.R., Furtado, A.A., Gomes, P.A.T.M., Fernandes-Pedrosa, M.F., Leite, A.C.L., Rêgo, M.J.B.M., Pitta, M.G.R., and Lemos, T.M.A.M., 2020, Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3ylidene)-N-phenyl-hydrazinecarbothioamide in mice, Braz. J. Med. Biol. Res., 53 (10), e10204.

[3] Zhen, X., Peng, Z., Zhao, S., Han, Y., Jin, Q., and Guan, L., 2015, Synthesis, potential anticonvulsant and antidepressant effects of 2-(5-methyl-2,3-dioxoindolin-1-yl)acetamide derivatives, Acta Pharm. Sin. B, 5 (4), 343–349.

[4] Dar, O.A., Lone, S.A., Malik, M.A., Aqlan, F.M., Wani, M.Y., Hashmi, A.A., and Ahmad, A., 2019, Synthesis and synergistic studies of Isatin based mixed ligand complexes as potential antifungal therapeutic agents, Heliyon, 5 (7), e02055.

[5] Subin Kumar, K., Reena, V.N., and Aravindakshan, K.K., 2021, Synthesis, anticancer and larvicidal activities of a novel Schiff base ligand, 3-((2-((1-(4-hydroxyphenyl)ethylidene)amino)ethyl)imino)-N-(p-tolyl)butanamide and its Mn(II), Fe(III), Co(II), Ni(II) and Zn(II) complexes, Results Chem., 3, 100166.

[6] Vairalaksmi, M., Princess, R., and Johnson Raja, S., 2019, The metal complexes of novel Schiff base containing isatin: Characterization, antimicrobial, antioxidant, and catalytic activity study, Asian J. Pharm. Clin. Res., 12 (8), 206–210.

[7] Khan, T., Raza, S., and Lawrence, A.J., 2022, Medicinal utility of thiosemicarbazones with special reference to mixed ligand and mixed metal complexes: A review, Russ. J. Coord. Chem., 48 (12), 877–895.

[8] Seema, S., Kumari, S., and Ranka, M., 2020, Mixed ligand complex of Ni(II) with Schiff base ligands derived from isatin and its bromo derivative: Synthesis, characterization and biological screening, Int. J. Chem. Sci., 18 (2), 301.

[9] Arshad, N., Mir, M.I., Perveen, F., Javed, A., Javaid, M., Saeed, A., Channar, P.A., Farooqi, S.I., Alkahtani, S., and Anwar, J., 2022, Investigations on anticancer potentials by DNA binding and cytotoxicity studies for newly synthesized and characterized imidazolidine and thiazolidine-based isatin derivatives, Molecules, 27 (2), 354.

[10] Jamil, W., Solangi, S., Ali, M., Khan, K.M., Taha, M., and Khuhawar, M.Y., 2019, Syntheses, characterization, in vitro antiglycation and DPPH radical scavenging activities of isatin salicylhydrazidehydrazone and its Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) metal complexes, Arabian J. Chem., 12 (8), 2262–2269.

[11] Sohrabi, M., Saeedi, M., Larijani, B., and Mahdavi, M., 2021, Recent advances in biological activities of rhodium complexes: Their applications in drug discovery research, Eur. J. Med. Chem., 216, 113308.

[12] Wu, Z., Zhang, Z., Ding, L., Xiang, M., and Luo, S., 2020, Development of a novel octahedron rhodium complex and its application to the alkynylation of isatin derivatives, Tetrahedron Lett., 61 (48), 152577.

[13] Albayati, A., Sheet, S., and Haydari, A., 2023, Synthesis and characterization of New binuclear complexes of Fe(II), Co(II), Zn (II), and Cd(II) with Schiff base ligands derived from isatins and amines, spectroscopic study and evaluation of their biological activity, Egypt. J. Chem., 66 (2), 411–424.

[14] Yan, X., Lv, Z., Wen, J., Zhao, S., and Xu, Z., 2018, Synthesis and in vitro evaluation of novel substituted isatin-propylene-1H-1,2,3-triazole-4-methylene-moxifloxacin hybrids for their anti-mycobacterial activities, Eur. J. Med. Chem., 143, 899–904.

[15] Chowdhary, S., Shalini, S., Arora, A., and Kumar, V., 2022, A mini review on Isatin, an anticancer scaffold with potential activities against neglected tropical diseases (NTDs), Pharmaceuticals, 15 (5), 536.

[16] Haj Mohammad Ebrahim Tehrani, K., Hashemi, M., Hassan, M., Kobarfard, F., and Mohebbi, S., 2016, Synthesis and antibacterial activity of Schiff bases of 5-substituted isatins, Chin. Chem. Lett., 27 (2), 221–225.

[17] Szklarzewicz, J., Jurowska, A., Matoga, D., Kruczała, K., Kazek, G., Mordyl, B., Sapa, J., and Papież, M., 2020, Synthesis, coordination properties and biological activity of vanadium complexes with hydrazone Schiff base ligands, Polyhedron, 185, 114589.

[18] Abdulghani, A.J., and Abbas, N.M., 2011, Synthesis characterization and biological activity study of new Schiff and Mannich bases and some metal complexes derived from isatin and dithiooxamide, Bioinorg. Chem. Appl., 2011, 706262.

[19] Maurya, M.R., Jangra, N., Avecilla, F., and Correia, I., 2018, 4,6‐Diacetyl resorcinol based vanadium(V) complexes: Reactivity and catalytic applications, Eur. J. Inorg. Chem., 2019 (2), 314–329.

[20] Nunes, P., Correia, I., Cavaco, I., Marques, F., Pinheiro, T., Avecilla, F., and Pessoa, J.C., 2021, Therapeutic potential of vanadium complexes with 1,10-phenanthroline ligands, quo vadis? Fate of complexes in cell media and cancer cells, J. Inorg. Biochem., 217, 111350.

[21] Damena, T., Zeleke, D., Desalegn, T., Demissie, T.B., and Eswaramoorthy, R., 2022, Synthesis, characterization, and biological activities of novel vanadium(IV) and cobalt(II) complexes, ACS Omega, 7 (5), 4389–4404.

[22] Askari, B., Rudbari, H.A., Valente, A., Bruno, G., Micale, N., Shivalingegowda, N., and Krishnappagowda, L.N., 2020, Synthesis, characterization and anticancer studies of Rh(I), Rh(III), Pd(II) and Pt(II) complexes bearing a dithiooxamide ligand, ChemistrySelect, 5 (2), 810–817.

[23] Das, U., Kar, B., Pete, S., and Paira, P., 2021, Ru(II), Ir(III), Re(I) and Rh(III) based complexes as next generation anticancer metallopharmaceuticals, Dalton Trans., 50 (32), 11259–11290.

[24] Zhong, H.J., Wang, W., Kang, T.S., Yan, H., Yang, Y., Xu, L., Wang, Y., Ma, D.L., and Leung, C.H., 2017, A rhodium(III) complex as an inhibitor of neural precursor cell expressed, developmentally down-regulated 8-activating enzyme with in vivo activity against inflammatory mowel disease, J. Med. Chem., 60 (1), 497–503.

[25] Mishra, N.K., Choi, M., Jo, H., Oh, Y., Sharma, S., Han, S.H., Jeong, T., Han, S., Lee, S.Y., and Kim, I.S., 2015, Direct C-H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis, Chem. Commun., 51 (97), 17229–17232.

[26] Tan, T.T.Y., and Hahn, F.E., 2019, Synthesis of iridium(III) and rhodium(III) complexes bearing C8-metalated theophylline ligands by directed C–H activation, Organometallics, 38 (9), 2250–2258.

[27] Naji, H.K., Al Hassani, R.A.M., and Balakit, A.A., 2022, Synthesis, characterization, and biological screening of Co(II), Ni(II), Cu(II), Pd(II), and Pt(IV) complexes of a novel hydrazide–hydrazone ligand derived from gallic acid, J. Pharm. Negat. Results, 13 (4), 1152–1159.

[28] Abdulsada, Z.S., Hassan, S.S., and Awad, S.H., 2023, Synthesis, characterization and biological activity of new oleander complexes against bacteria found in polluted water, Indones. J. Chem., 23 (6), 1638–1651.

[29] Ward, H.A., Musa, T.M., and Nasif, Z.N., 2022, Synthesis and characterization of some transition metals complexes with new ligand azo imidazole derivative, Al-Mustansiriyah J. Sci., 33 (2), 31–38.

[30] Al-Alzawi, S.M., Al-Jibouri, M.N., Rasheed, A.M., and Al-Bayati, S.M., 2023, Synthesis, characterization and antimicrobial activity of complexes metal ions Ni(II), Zn(ΙΙ), Pd(II) and Pt(IV) with polydentate 1,2,4-triazole ligand, Indones. J. Chem., 23 (1), 210–218.

[31] Kooij, B., Zhaowen, D., Varava, P., Fadaei-Tirani, F., Scopelliti, R., Piveteau, L., and Severin, K., 2022, Vanadium complexes with N-heterocyclic vinylidene ligands, Chem. Commun., 58 (26), 4204–4207.

[32] Justim, J.R., Bohs, L.M.C., Martins, B.B., Bandeira, K.C.T., de Melo, A.P.L., Gervini, V.C., Bresolin, L., Godoi, M., and Peixoto, C.R.M., 2021, Electrochemical characterization of isatin-thiosemicarbazone derivatives, J. Chem. Sci., 133 (4), 124.

[33] Reda, S.M., and Al-Hamdani, A.A.S., 2023, Mn(II),Fe(III),Co(II)and Rh(III) complexes with azo ligand: Synthesis, characterization, thermal analysis and bioactivity, Baghdad Sci. J., 20 (3), 642–660.

[34] Kumari, A., 2019, Analysis of transition metal complexes of rhodium(III) containing trans–(14)–diene, Int. J. Adv. Acad. Stud., 1 (1), 76–78.

[35] Al-Bayati, S., Alazawi, S., Al-Barody, S., Rasheed, A., and Alhassani, R., 2024, Synthesis of manganese(II), iron(III), and vanadium(IV) complexes with new Schiff bases and their spectroscopic and thermal studies and evaluation of their antimicrobial activity, J. Turk. Chem. Soc., Sect. A, 11 (1), 103–114.

[36] Yusenko, K.V., Sukhikh, A.S., Kraus, W., and Gromilov, S.A., 2020, Synthesis and crystal chemistry of octahedral rhodium(III) chloroamines, Molecules, 25 (4), 768.

[37] Sharma, B.P., Pandey, S.K., Marasini, B.P., Shrestha, S., and Sharma, M.L., 2021, Oxovanadium(IV) complexes with triazole based Schiff base ligands: Synthesis, characterization and antibacterial study, J. Nepal Chem. Soc., 42 (1), 56–63.



DOI: https://doi.org/10.22146/ijc.91731

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