Synthesis and Antiproliferative Activity of Novel Hydrazono Thiazolidene and Thiazole Derivatives Bearing Rhodanine Moiety
M. E. A. Elasasy, D. H. Elnaggar, N. A. Abdel Hafez, M. E. Azab, A. E. Amr, M. M. Omran, A. M. Mohamed
Российский журнал общей химии
https://doi.org/10.1134/S1070363221050236
Some new fluoro-heterocyclic compounds containing thiazole and pyridine moities have been synthesized and studied for their antiproliferative activity. Thiazole derivatives have been synthesized by the reaction of alpha-halo carbonyl compounds with thiosemicarbazones. Some pyridine derivatives have been synthesized by the reaction of chalcone with cyanothioacetamide and/or malononitrile. Spectroscopic methods have been used for elucidating molecular structures of the products. Cytotoxic activity of several derivatives has been tested against human breast cancer (MCF-7), human colon cancer (HCT-116) and human liver cancer (Hep-G2) by the SRB method. Most of compounds exhibit mild effect on the tested cell lines. One of thiazolidin-4-one derivatives has been characterized by moderate to strong effect on MCF-7 cell line.
- Applied Organic Chemistry Department, National Research Centre, Dokki, 12622, Giza, EgyptM. E. A. Elasasy, D. H. Elnaggar, N. A. Abdel Hafez & A. M. Mohamed
- Chemistry Department, Faculty of Science, Ain Shams University, Abbasia, 11566, Cairo, EgyptM. E. Azab
- Pharmaceutical Chemistry Department, Drug Exploration and Development Chair (DEDC), College of Pharmacy, King Saud University, 11451, Riyadh, Saudi ArabiaA. E. Amr
- Organic Chemistry Department, Chemical Industries Research Division, National Research Centre, 12622, Cairo, EgyptA. E. Amr
- Cancer Biology Department, Pharmacology Unit, National Cancer Institute, Cairo University, 11796, Cairo, EgyptM. M. Omran
- Krithika, U., Prabitha, P., Mandal, S., Yuvaraj, S., Priya, D., Wadhwani, A., and Kumar, B., Med Chem. (Shariqah (United Arab Emirates)), 2020.
- Abdel Hafez, N.A., Elsayed, M.A., El-Shahawi, M.M., Awad, G.E, and Ali, K.A., J. Heterocycl. Chem., 2018, vol. 55, no. 3, pp. 685–691.
- Elnaggar, D.H., Abdel Hafez, N.A., Rashdan, H.R., Abdelwahed, N.A., Awad, H.M, and Ali, K.A., Mini Rev. Med. Chem., 2019, vol. 19, no. 20, pp. 1717–1725. https://doi.org/10.2174/1389557519666190722123422
- Mousavi, S.M., Zarei, M., Hashemi, S.A., Babapoor, A., and Amani, A.M., Artif. Cells Nanomed. Biotechnol., 2019, vol. 47, no. 1, pp. 1132–1148. https://doi.org/10.1080/21691401.2019.1573824
- Ahmed, M.F., Belal, A., and Youns, M., Med. Chem. Res., 2015, vol. 24, no. 7, pp. 2993–3007. https://doi.org/10.1007/s00044-015-1357-1
- Ganesamoorthy, T. and Ganesan, V., Arab. J. Chem., 2014, vol. 7, no. 6, pp. 1055–1064. https://doi.org/10.1016/j.arabjc.2010.10.034
- Deng, H., O’Hagan, D., and Schaffrath, C., Nat. Prod. Rep., 2004, vol. 21, no. 6, pp. 773–784. https://doi.org/10.1039/b415087m
- Quenelle, D.C., Keith, K.A, and Kern, E.R., Antivir. Res., 2006, vol. 71, no. 1, pp. 24–30. https://doi.org/10.1016/j.antiviral.2006.02.010
- Afrasiabi, Z., Sinn, E., Padhye, S., Dutta, S., Padhye, S., Newton, C., Anson, C.E., and Powell, A.K., J. Inorg. Biochem. 2003, vol. 95, no. 4, pp. 306–314.
- Yousef, T.A., Badria, F.A., Ghazy, S.E., ElGammal, O.A., and El-Reash, G.M.A., Int. J. Med. Med. Sci., 2011, vol. 3, no. 2, pp. 37–46.
- Patil, V., Tilekar, K., Mehendale–Munj, S., Mohan, R., and Ramaa, C., Eur. J.Med. Chem., 2010, vol. 45, no. 10, pp. 4539–4544. https://doi.org/10.1016/j.ejmech.2010.07.014
- Jeong, T.-S., Kim, J.-R., Kim, K.S., Cho, K.-H., Bae, K.-H., and Lee, W.S., Bioorg. Med. Chem., 2004, vol. 12, no. 15, pp. 4017–4023. https://doi.org/10.1016/j.bmc.2004.06.001
- Habib, N., Rida, S.M., Badawey, E., Fahmy, H., and Ghozlan, H., Eur. J. Med. Chem., 1997, vol. 32, no. 9, pp. 759–762. https://doi.org/10.1016/S0223-5234(97)88919-2
- Cutshall, N.S., O’Day, C, and Prezhdo, M., Bioorg. Med. Chem. Lett., 2005, vol. 15, no. 14, pp. 3374–3379. https://doi.org/10.1016/j.bmcl.2005.05.034
- Wang, L., Kong, F., Kokoski, C.L., Andrews, D.W., and Xing, C., Bioorg. Med. Chem. Lett., 2008, vol. 18, no. 1, pp. 236–240. https://doi.org/10.1016/j.bmcl.2007.10.088
- Khalaf, H.S., Tolan, H.E., Radwan, M.A., Mohamed, A.M., Awad, H.M., and El-Sayed, W.A., Nucleosides Nucleotides Nucleic Acids, 2020, vol. 39, no. 7, pp. 1036–1056. https://doi.org/10.1080/15257770.2020.1748649
- Mohamed, A.M., Abdel-Hafez, N., Kassem, A., Abbas, E., and Mounier, M., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, pp. 2391–2400. https://doi.org/10.1134/S1070363217100218
- Mohamed, A.M., Al-Qalawi, H.R., El-Sayed, W.A., Arafa, W.A., Alhumaimess, M.S., and Hassan, A.K., Acta Pol. Pharm., 2015, vol. 72, no. 2, pp. 307–318.
- Mohamed, A.M., El-Sayed, W.A., Alsharari, M.A., Al-Qalawi, H.R., and Germoush, M.O., Arch. Pharmacal Res., 2013, vol. 36, no. 9, pp. 1055–1065. https://doi.org/10.1007/s12272-013-0163-x
- Ali, K.A., Elsayed, M.A., and Farag, A.M., Heterocycles, 2012, vol. 85, no. 8, pp. 1913–1923. https://doi.org/10.3987/COM-12-12483
- Mohamed, A.M., Amr, A.E., Alsharari, M.A., AlQalawi, H.R.M., Germoush, M.O., and Al-Omar, M.A., Am. J. Biochem. Biotechnol., 2011, vol. 7, no. 2, pp. 43–54.
- Rashad, A.E., El-Sayed, W.A., Mohamed, A.M., and Ali, M.M., Arch. Pharm. , 2010, vol. 343, no. 8, pp. 440–448. https://doi.org/10.1002/ardp.201000002
- El-Naggar, M., Sallam, H.A., Shaban, S.S., AbdelWahab, S.S., Amr, A.E.-G., Azab, M.E., Nossier, E.S., and Al-Omar, M.A., Molecules, 2019, vol. 24, no. 6, p. 1066. https://doi.org/10.3390/molecules24061066
- Youssef, A.S., Hemdan, M.M., Azab, M.E., Emara, S.A., Elsayed, G.A., and Kamel, R.M., J. Heterocycl. Chem., 2020, vol. 57, no. 3, pp. 1133–1142. https://doi.org/10.1002/jhet.3850
- Liu, J., Yi, W., Wan, Y., Ma, L., and Song, H., Bioorg. Med. Chem., 2008, vol. 16, no. 3, pp. 1096–1102. https://doi.org/10.1016/j.bmc.2007.10.102
- Martínez, J., Pereira, M. T., Ortigueira, J.M., Bermúdez, B., Antelo, J.M., Fernández, A., and Vila, J.M., Polyhedron, 2012, vol. 31, no. 1, pp. 217–226.
- Xiabing, M., Ablajan, K., Obul, M., Seydimemet, M., Ruzi, R., and Wenbo, L., Tetrahedron, 2016, vol. 72, no. 18, pp. 2349–2353. https://doi.org/10.1016/j.tet.2016.03.053
- Sardari, S., Feizi, S., Rezayan, A. H., Azerang, P., Mohammad Shahcheragh, S., Ghavami, G., and Habibi, A., Iran. J. Pharm. Sci.: IJPR, 2017, vol. 16, no. 3, p. 1128.
- Srour, A.M., El-Bayaa, M.N., Omran, M.M., Sharaky, M.M., and El-Sayed, W.A., Anti-Cancer Agents Med. Chem, 2020.
- Sharaky, M., Kamel, M., Aziz, M. A., Omran, M., Rageh, M.M., Abouzid, K.A., and Shouman, S.A., J. Enzyme Inhib. Med. Chem., 2020, vol. 35, no. 1, pp. 1641–1656.
- Kalmouch, A., Rdwan, M., Omran, M., Sharaky, M., and Moustafa, G., Egypt. J. Chem., 2020, vol. 63, no. 11, pp. 3–6.