New Pd(II) complexes containing hydrazinyl oxazolyl coumarin derivatives: synthesis, spectral characterization and anti-cancer studies

New Pd(II) complexes containing hydrazinyl oxazolyl coumarin derivatives: synthesis, spectral characterization and anti-cancer studies Sheikdawood Parveen BioInspired Material Research Laboratory, Dr. Mahalingam College of Engineering and Technology, Pollachi , Coimbatore 642 003 , India Ganesan Deebakkrishnan Department of Chemistry , Karpagam Academy of Higher Education (Deemed to be University) , Coimbatore 641 021 , India Arumugam Kosiha School of Basic Sciences , Vels Institute of Science, Technology & Advanced Studies (Deemed to be University) , Chennai 600 117 , India Giriraj Kalaiarasi Department of Chemistry , Karpagam Academy of Higher Education (Deemed to be University) , Coimbatore 641 021 , India Centre for Material Chemistry, Karpagam Academy of Higher Education (Deemed to be University) , Coimbatore 641 021 , India Abstract

New palladium(II) complexes containing coumarin derivatives such as (E)-3(2-(2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)hydrazinyl)oxazol-4-yl)-2H-chromen-2-one ( HL 1 ), (E)-7-hydroxy-3(2-(2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)hydrazinyl)oxazol-4-yl)-2H-chromen-2-one ( HL 2 ) were successfully designed and synthesized from the reaction of K 2 [PdCl 4 ] with ligands HL 1&2 with in Methanol medium. The ligands and complexes were characterized by various analytical and spectral techniques such as FT-IR, UV–Vis, 1 H NMR and 13 C NMR spectral techniques. From the spectral data we confirmed that the ligands neutrally coordinated with Pd(II) ion via their lactone oxygen, azomethine nitrogen and oxazolyl ring nitrogen atoms. The electrolytic nature of the complexes was confirmed by using conductivity experiments. Further anticancer activity of the compounds has examined with HeLa (human cervical cancer) cells along with the cisplatin as positive control and the obtained results revealed that the complexes possess significant anticancer activity and non-toxic towards HUVEC (human umbilical vein endothelial) cells.
02 26 2024 12 06 2023 02 01 2024 261 274 10.1515/zpch-2023-0380 10.1515/zpch-2023-0380 https://www.degruyter.com/document/doi/10.1515/zpch-2023-0380/html https://www.degruyter.com/document/doi/10.1515/zpch-2023-0380/pdf https://www.degruyter.com/document/doi/10.1515/zpch-2023-0380/xml 10.1002/pon.5826 Link, E., Baumann, E. Psycho. Oncol. 2022, 31, 442–449; https://doi.org/10.1002/pon.5826. 10.1016/j.ccr.2021.214307 Paprocka, R., Szadkowska, M. W., Janciauskiene, S., Kosmalski, T., Kulik, M., Basa, A. H. Coord. Chem. Rev. 2022, 452, 214307; https://doi.org/10.1016/j.ccr.2021.214307. 10.1039/D1CS00609F Gourdon, L., Cariou, K. G., Gasser, G. Chem. Soc. Rev. 2022, 51, 1167–1195; https://doi.org/10.1039/d1cs00609f. 10.1016/j.jinorgbio.2016.11.010 Scalese, G., Correia, I., Benitez, J., Rostan, S., Marques, F., Mendes, F., Matos, A. P., Pessoa, J. C., Gambino, D. J. Inorg. Biochem. 2017, 166, 162–172; https://doi.org/10.1016/j.jinorgbio.2016.11.010. 10.1016/j.jinorgbio.2023.112144 Bazsefidpar, P., Eftekhar, E., Jahromi, M. Z., Nikpoor, A. R., Moghadam, M. E., Zolghadri, S. J. Inorg. Biochem. 2023, 241, 112144; https://doi.org/10.1016/j.jinorgbio.2023.112144. 10.1021/jm100020w Gasser, G., Ott, I., Nolte, N. M. J. Med. Chem. 2011, 54, 3–25; https://doi.org/10.1021/jm100020w. 10.1016/j.biotechadv.2012.10.002 Kumar, A., Zhang, X., Liang, X. J. Biotechnol. Adv. 2013, 31, 593–606; https://doi.org/10.1016/j.biotechadv.2012.10.002. 10.1016/j.cbpa.2019.11.001 Benjamin, S., Murray, L., Dyson, P. J. Curr. Opin. Chem. Biol. 2020, 56, 28–34. 10.1039/C4CS00063C Kapdi, A. R., Fairlamb, I. J. S. Chem. Soc. Rev. 2014, 43, 4751–4777; https://doi.org/10.1039/c4cs00063c. 10.1080/14756366.2018.1471687 Surażyński, A., Muszynska, A., Gornowicz, A., Bielawska, A., Bielawski, K. J. Enzy. Inhib. Med. Chem. 2018, 33, 1006–1023. 10.1016/j.ica.2011.03.048 Mukherjee, S., Chowdhury, S., Chattapadhyay, A. P., Bhattacharya, A. Inorg. Chim. Acta 2011, 373, 40–46; https://doi.org/10.1016/j.ica.2011.03.048. 10.1016/j.ejmech.2017.12.027 Li, Y., Gu, Z., Zhan, C., Li, S., Zhang, L., Zhou, G., Wang, S., Zhang, J. Eur. J. Med. Chem. 2018, 144, 662–671; https://doi.org/10.1016/j.ejmech.2017.12.027. 10.1016/j.biochi.2020.05.010 Erkisa, M., Aydinlik, S., Cevatemre, B., Aztopal, N., Akar, R. O., Celikler, S., Yilmaz, V. T., Ari, F., Ulukaya, E. A. Biochimie 2020, 175, 159–172; https://doi.org/10.1016/j.biochi.2020.05.010. 10.2174/187152007781668661 Caires, A. C. Anti-Cancer Agents Med. Chem. 2007, 7, 484–491; https://doi.org/10.2174/187152007781668661. 10.1016/j.jinorgbio.2021.111590 Zafar, M. N., Butt, A. M., Perveen, F., Nazar, M. F., Masood, S., Dalebrook, A. F., Mughal, E. U., Sumrra, S. H., Sung, Y. Y., Muhammad, T. S. T., Wright, L. J. J. Inorg. Biochem. 2021, 224, 111590; https://doi.org/10.1016/j.jinorgbio.2021.111590. 10.1021/acs.inorgchem.3c01172 Komlyagina, V. I., Romashev, N. F., Besprozvannykh, V. K., Arakelyan, J., Wu, C., Chubarov, A. S., Bakaev, I. V., Soh, Y. K., Abramov, P. A., Cheung, K. L., Kompan’kov, N. B., Ryadun, A. A., Babak, M. V., Gushchin, A. L. Inorg. Chem. 2023, 62, 11541; https://doi.org/10.1021/acs.inorgchem.3c01172. 10.1016/j.ica.2022.121368 Pooyan, M., Shariatinia, Z., Mohammadpanah, F., Gholivand, K., Junk, P. C., GuoSatari, Z. M., Charandabi, V. N. Inorg. Chim. Acta 2023, 547, 121368; https://doi.org/10.1016/j.ica.2022.121368. 10.1002/ardp.202000025 Song, X. F., Fan, J., Liu, L., Liu, X. F., Gao, F. Archiv der Pharmazie 2020, 353, 2000025; https://doi.org/10.1002/ardp.202000025. 10.1016/j.ejmech.2020.112832 Qin, H. L., Zhang, Z. W., Ravindar, L., Rakesh, K. Eur. J. Med. Chem. 2020, 207, 112832; https://doi.org/10.1016/j.ejmech.2020.112832. 10.1016/j.ejmech.2014.03.029 Sánchez-Recillas, A., Navarrete-Vázquez, G., Hidalgo-Figueroa, S., Rios, M. Y., Ibarra-Barajas, M., Estrada Soto, S. Eur. J. Med. Chem. 2014, 77, 400–408; https://doi.org/10.1016/j.ejmech.2014.03.029. Vogel, A. I. Practical Organic Chemistry; Long Man Group Ltd: London, 1974. 10.1016/j.ica.2022.120846 Kalaiarasi, G., Ranjani, M., Prabhakaran, R., Athira, P. R., Kosika, A. Inorg. Chim. Acta 2022, 535, 120846; https://doi.org/10.1016/j.ica.2022.120846. 10.1002/ejic.202100039 Kalaiarasi, G., Mohankumar, A., Dharani, S., Dallemer, F., Sundararaj, P., Prabhakaran, R. Eur. J. Inorg. Chem. 2021, 2021, 1383–1396; https://doi.org/10.1002/ejic.202100039. 10.1039/C9DT02663K Kalaiarasi, G., Dharani, S., Lynch, V., Prabhakaran, R. Dalton Trans. 2019, 48, 12496–12511; https://doi.org/10.1039/c9dt02663k. 10.1016/S0020-1693(00)81214-1 Saha, N., Bhattacharyya, D., Mukherjee, D. Inorg. Chim. Acta 1986, 125, 213–217; https://doi.org/10.1016/s0020-1693(00)81214-1. 10.1007/s00044-017-1820-2 Khan Yusufzai, S., Osman, H., Khan, M. S., Mohamad, S., Sulaiman, O., Parumasivam, T., Gansau, J. A., Johansah, N., Noviany. Med. Chem. Res. 2017, 26, 1139–1148; https://doi.org/10.1007/s00044-017-1820-2. 10.1021/acs.inorgchem.9b00794 Dharani, S., Kalaiarasi, G., Sindhuja, D., Lynch, V. M., Shankar, R., Karvembu, R., Prabhakaran, R. Inorg. Chem. 2019, 58, 8045–8055; https://doi.org/10.1021/acs.inorgchem.9b00794. 10.1002/cbic.202100015 Silva, M. J., Gois, P. M., Gasser, G. Chem. Bio. Chem. 2021, 22, 1740–1742; https://doi.org/10.1002/cbic.202100015. 10.1016/j.bmc.2014.06.039 Ari, F., Cevatemre, B., Armutak, E. I. I., Aztopal, N., Yilmaz, V. T., Ulukaya, E. Bioorg. Med. Chem. 2014, 22, 4948–4954; https://doi.org/10.1016/j.bmc.2014.06.039. 10.1016/S0010-8545(97)00023-4 Hambley, T. W. Coord. Chem. Rev. 1997, 166, 181–223; https://doi.org/10.1016/s0010-8545(97)00023-4. 10.1016/j.ica.2020.119868 Ayyanaan, G., Mohanraj, M., Gopiraman, M., Uthayamalar, R., Raja, G., Bhunanesh, S., Nandhakumar, R., Jayabalakrishnan, C. Inorg. Chim. Acta 2020, 512, 119868. 10.1016/j.ica.2017.05.044 Murali Shankar, M., Basheer, S. M., Haribabu, J., Bhuvanesh, N. S. P., Karvembu, R., Sreekanth, A. Inorg. Chim. Acta 2017, 466, 61–70. 10.1039/D3NJ02067C Haribabu, J., Nithya, B., Srividya, S., Dorairaj, D. P., Azam, M., Mohammed Subarkhan, M. S., Chang, Y. L., Hsu, S. C. N., Starha, P., Karvembu, R. New J. Chem. 2023, 47, 15748–15759; https://doi.org/10.1039/d3nj02067c. 10.1039/c2dt30990d Gao, E., Lin, L., Liu, L., Zhu, M., Wang, B., Gao, X. Dalton Trans. 2012, 41, 11187–11194; https://doi.org/10.1039/c2dt30990d. 10.1002/anie.201602814 Tsz-Him, F. T., Lok, C. N., Yik-Sham, C. C., Eva Fung, Y. M., Chow, P. K., Wan, P. K., Che, C. M. Angewandte 2016, 55, 11935–11939. 10.1016/j.jinorgbio.2020.111156 Omondi, R. O., Bellam, R., Ojwach, S. O., Jaganyi, D., Fatokun, A. A. J. Inorg. Biochem. 2020, 210, 111156; https://doi.org/10.1016/j.jinorgbio.2020.111156. 10.1016/j.jinorgbio.2019.110857 Wei, X., Yang, Y., Ge, J., Lin, X., Liu, D., Wang, S., Zhang, J., Zhou, G., Li, S. J. Inorg. Biochem. 2020, 202, 11085. 10.1016/j.ejmech.2008.07.033 Gligorijevic, N., Todorovic, T., Radulovic, S., Sladic, D., Filipovic, N., Gođevac, D., Jeremic, D., Anđelkovic, K. Eur. J. Med. Chem. 2009, 44, 1623–1629; https://doi.org/10.1016/j.ejmech.2008.07.033. 10.1155/2016/7508724 Abu-Safieh, K. A., Abu-Surrah, A. S., Tabba, H. D., AlMasri, H. A., Bawadi, R. M., Boudjelal, F. M., Tahtamouni, L. H. J. Chem. 2016, 2016, 7508724. 10.1016/j.jinorgbio.2010.07.002 Vrzal, R., Štarha, P., Dvořák, Z., Trávníček, Z. J. Inorg. Biochem. 2010, 104, 1130–1132; https://doi.org/10.1016/j.jinorgbio.2010.07.002. 10.1016/j.bmc.2017.01.033 Kacar, O., Cevatemre, B., Hatipoglu, I., Arda, N., Ulukaya, E., Yilmaz, V. T., Acilan, C. Bioorg. Med. Chem. 2017, 25, 1770–1777; https://doi.org/10.1016/j.bmc.2017.01.033. 10.1016/j.molliq.2023.121541 Dhanya, R., Rajamanikandan, R., Ilanchelian, M. J. Mol. Liq. 2023, 377, 121541. 10.1016/j.dyepig.2023.111746 Dhanya, R., Rajamanikandan, R., Ilanchelian, M. Dyes Pigm. 2023, 220, 111746.