Research Article

The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations

Volume: 13 Number: 2 June 18, 2021
EN TR

The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations

Abstract

A series of 1-8 different ferrocenyl chalcones were synthesized through the Claisen–Schmidt condensation and the Friedel−Crafts acylation. Their structures were confirmed by means of 1H, 13C NMR and FT-IR. The cytotoxic and antiproliferative activities of the chalcones were screened against HeLa (cervix cancer) and PC3 (prostate cancer) cell lines. They showed excellent anti-cancer activities especially against PC3 cell even at very low concentration (5 µM). Also, their physicochemical properties, drug-likeness calculations and the rule of five (RO5) were investigated.

Keywords

Ferrocene, Chalcone, PC3, HeLa, Anti-cancer, Drug-likeness

Supporting Institution

Scientific Research Projects Coordination Unit of Kırıkkale University

Project Number

2018/85

References

  1. Baba, K., Nakata, K., Taniguchi, M., Kido, T., & Kozawa, M. (1990). Chalcones from Angelica keiskei. Phytochemistry, 29, 3907-3910. https://doi.org/10.1016/0031-9422(90)85357-L
  2. Boumendjel, A., Ronot, X., & Boutonnat, J. (2009). Chalcones Derivatives Acting as Cell Cycle Blockers: Potential Anti Cancer Drugs?. Current Drug Targets, 10, 363-371. https://doi.org/10.2174/138945009787846416
  3. Dogan, Ö., Şenol, V., Zeytinci, H., Koyuncu, H., & Bulut, A. (2005). Efficient synthesis of ferrocenylenones by Friedel-Crafts acylation with EtAlCl2-Me3Al. Journal of Organometallic Chemistry, 690, 430-434. https://doi:10.1016/j.jorganchem.2004.09.055
  4. Hano, Y., Ichikawa, K., Okuyama, M., Yamanaka, J., Miyoshi, T., & Nomura, T. (1995). Sanggenons R, S, and T, three new isoprenylated phenols from the Chinese crude drug Sang-Bai-Pi (Morus root bark). Heterocycles, 2, 953–965. http://doi.org/10.3987/COM-94-S96
  5. Harborne, J. B., Mabry, T. J., & Mabry, H. (1975). The flavonoids. Chapman and Hall, London. https://doi.org/10.1007/978-1-4899-2909-9
  6. Janka, V., Zatko, D., Ladislav, V., Pal, P., & Gabriela, M. (2015). Some ferrocenyl chalcones as useful candidates for cancer treatment. In Vitro Cellular & Development Biology-Animal, 51, 964–974. http://doi.org/10.1007/s11626-015-9919-6
  7. Kakati, D., & Sarma, J. C. (2011). Microwave-assisted solvent free synthesis of 1, 3-diphenyl propenones. Chemistry Central Journal, 5(1), 8. https://doi.org/10.1186/1752-153X-5-8
  8. Li, Y., Ishibashi, M., Chen, X., & Ohizumu, Y. (2003). Littorachalcone, a new enhancer of NGF-mediated neurite outgrowth, from Verbena littoralis. Chemical & Pharmaceutical Bulletin, 51, 872-874. https://doi.org/10.1248/cpb.51.872
  9. Lopez, J.A., Barillas, W, Gomez-Laurito, J, Martin, G.E., Lin, F.T., Al-Rehaily, A.J., Zemaitis, M.A., & Schiff, P.L. (1998). Galiposin: a new β-hydroxy chalcone from Galipea granulosa. Planta Medica, 64, 76–77. http://doi.org/10.1055/s-2006-957373
  10. Masesane, I.B., Yeboah, S.O., Liebscher, J., Mügge, C., & Abegaz, B.M. (2000). A bichalcone from the twigs of Rhus pyroides. Phytochemistry, 53, 1005–1008. . https://doi.org/10.1016/S0031-9422(99)00553-1
APA
Albayrak, E., Işılar, Ö., Bıyıkoğlu, M., Şahin Yağlıoğlu, A., & Bulut, A. (2021). The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations. International Journal of Engineering Research and Development, 13(2), 690-703. https://doi.org/10.29137/umagd.927358
AMA
1.Albayrak E, Işılar Ö, Bıyıkoğlu M, Şahin Yağlıoğlu A, Bulut A. The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations. IJERAD. 2021;13(2):690-703. doi:10.29137/umagd.927358
Chicago
Albayrak, Emine, Özer Işılar, Mutluhan Bıyıkoğlu, Ayşe Şahin Yağlıoğlu, and Adnan Bulut. 2021. “The Synthesis and Anti-Cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations”. International Journal of Engineering Research and Development 13 (2): 690-703. https://doi.org/10.29137/umagd.927358.
EndNote
Albayrak E, Işılar Ö, Bıyıkoğlu M, Şahin Yağlıoğlu A, Bulut A (June 1, 2021) The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations. International Journal of Engineering Research and Development 13 2 690–703.
IEEE
[1]E. Albayrak, Ö. Işılar, M. Bıyıkoğlu, A. Şahin Yağlıoğlu, and A. Bulut, “The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations”, IJERAD, vol. 13, no. 2, pp. 690–703, June 2021, doi: 10.29137/umagd.927358.
ISNAD
Albayrak, Emine - Işılar, Özer - Bıyıkoğlu, Mutluhan - Şahin Yağlıoğlu, Ayşe - Bulut, Adnan. “The Synthesis and Anti-Cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations”. International Journal of Engineering Research and Development 13/2 (June 1, 2021): 690-703. https://doi.org/10.29137/umagd.927358.
JAMA
1.Albayrak E, Işılar Ö, Bıyıkoğlu M, Şahin Yağlıoğlu A, Bulut A. The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations. IJERAD. 2021;13:690–703.
MLA
Albayrak, Emine, et al. “The Synthesis and Anti-Cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations”. International Journal of Engineering Research and Development, vol. 13, no. 2, June 2021, pp. 690-03, doi:10.29137/umagd.927358.
Vancouver
1.Emine Albayrak, Özer Işılar, Mutluhan Bıyıkoğlu, Ayşe Şahin Yağlıoğlu, Adnan Bulut. The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations. IJERAD. 2021 Jun. 1;13(2):690-703. doi:10.29137/umagd.927358