Anticancer activity of some new series of 2-(substituted)amino-1,3-thiazole derivatives

Bakare, Safyah B.

doi:10.2478/pjct-2019-0025

Abstract

A series of thiazole derivatives were synthesized and structurally elucidated by IR, ¹H NMR, ¹³C NMR, mass and elemental analyses. The prepared compounds were screened for their cytotoxic activity against Leukemia HL-60 cell line. Compound 4b was considered as the most promising antitumor candidate among the tested compounds. Mechanism of action of compound 4b evaluated by flow cytometric assay revealed cell cycle arrest at G2/M phase and pre-G1 apoptosis. The ratio of apoptosis was also determined. Moreover, compound 4b increased the concentration of caspase 3 by 4 fold more than untreated control.

References

1. Schnurch, M., Waldner, Hilber, K. & Mihovilovic, M. D. (2011). Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters. Bioorg. Med. Chem. Lett., 21(7), 2149–2154. doi.org/10.1016/j.bmcl.2011.01.123.10.1016/j.bmcl.2011.01.123
Open DOI Search in Google Scholar Back to article
2. Yadav, P.S., Devprakash & SenthilKumar, G.P. (2011). Benzothiazole: different methods of synthesis and diverse biological activities. Int. Pharm. Sci. Drug Res., 3, 1–7.10.1002/chin.201140238
Search in Google Scholar Back to article
3. Zaki, I., Abdelhameid, M.K., El-Deen, I.M., Wahab, A.H. A.A., Ashmawy, A.M. & Mohamed, K.O. (2018). Design, synthesis and screening of 1, 2, 4-triazinone derivatives as potential antitumor agents with apoptosis inducing activity on MCF-7 breast cancer cell line. Eur. J. Med. Chem., 156, 563–579. doi.org/10.1016/j.ejmech.2018.07.003.10.1016/j.ejmech.2018.07.003
Open DOI Search in Google Scholar Back to article
4. Hassan, F.A. (2012). Synthesis, characterization, anti-inflammatory, and antioxidant activities of some new thiazole derivatives. Int. J. Appl. Sci. Technol., 2, 180–187.
Search in Google Scholar Back to article
5. El-Sayed, E.H., Moustafa, A.Y., & El-Ata, S.A.A. (2018). Synthesis of New 2-N-Substituted Amino-5-aryl-1,3-thiazoles as Antitumor Agents. Latin Amer. J. Pharm., 37, 1594–1601.
Search in Google Scholar Back to article
6. Al-Ghareb, M.S., El-Hady, H.A. & Abd-Allah, R.M. (2018). In Vitro Antitumor Evaluation of Some New Tetra Substituted 1,2,4-Triazines. Latin Amer. J. Pharm., 37, 1035–1045.
Search in Google Scholar Back to article
7. Minh-An, T.N., Kumar, M.A., Chang, S.H., Kim, M.P., Kim, J.A. & Lee, K.D. (2014). Synthesis, Anticancer and Antioxidant Activity of Novel 2,4-Disubstituted Thiazoles. Bull. Korean Chem. Soc., 35(6), 1619–1624. https://doi.org/10.5012/bkcs.2014.35.6.1619.10.5012/bkcs.2014.35.6.1619
Open DOI Search in Google Scholar Back to article
8. Mahmoodi, N.O., Parvizi, J., Sharifzadeh, B. & Rassa, M. (2013). Facile Regioselective Synthesis of Novel bis Thiazole Derivatives and Their Antimicrobial Activity. Arch. Pharm. Chem. Life Sci., 346(12), 860–864. doi.org/10.1002/ardp.201300187.10.1002/ardp.201300187
Search in Google Scholar Back to article
9. Silverman, R.B. (1992). The Organic Chemistry Of Drug Design And Drug Action, Academic Press; London, 12, 263.
Search in Google Scholar Back to article
10. Pani, A., Mrongiu, M.E., Pinna, E., Scintu, F., Perra. C., Demontis, A., Manfredini, S. & La-Colla, P. (1998). In vitro and in vivo antiproliferative activity of IPCAR, a new pyrazole nucleoside analog. Anticancer Res., 18, 2623–2630.
Search in Google Scholar Back to article
11. Krapcho, A.P., Menta, E., Olive, A., Didomenica, R., Fiocchi, L., Maroesch, M.E., Gallagher, C.E., Hacker, M.P., Beggiolin, G., Giullani, F.C., Pezzoni, G. & Spinelli, S. (1998). Synthesis and Antitumor Evaluation of 2,5-Disubstituted-Indazolo[4,3-gh]isoquinolin-6(2H)-ones (9-Aza-anthrapyraz oles). J. Med. Chem., 41, 5429–5444. DOI: 10.1021/jm9804432.10.1021/jm9804432
Open DOI Search in Google Scholar Back to article
12. Daidone, G., Maggio, B., Plescia, S., Raffa, D., Musiu, C., Milia, C., Perra, G., & Marongiu, M.E. (1998). Antimicrobial and antineoplastic activities of new 4-diazopyrazole derivatives. Eur. J. Med. Chem., 33, 375–382. doi.org/10.1016/S0223-5234(98)80004-4.10.1016/S0223-5234(98)80004-4
Open DOI Search in Google Scholar Back to article
13. Kubba, A.A.R.M. & Rahim, N.A.H.A. (2018). Synthesis and antimicrobial evaluation of new-[2-amino-4-(4-chloro-/4-bromophenyl)-1,3-thiazole derivatives. J. Pharm. Res., 12(1), 145–150.
Search in Google Scholar Back to article
14. de Santa, T.I., de Oliveira Barbosa, M., de Moraes Gomes P.A.T., da Cruz A.C.N., da Silva, T.G. & Leita, A.C.L. (2018). Synthesis, anticancer activity and mechanism of action of new thiazole derivatives. Eur. J. Med. Chem., 144, 874–886. doi. org/10.1016/j.ejmech.2017.12.040.10.1016/j.ejmech.2017.12.04029329071
Open DOI Search in Google Scholar Back to article

Anticancer activity of some new series of 2-(substituted)amino-1,3-thiazole derivatives

Abstract

Paradigm

My account