Synthesis and cytotoxicity evaluation of chalcone derivatives

Hua Huu Bang * , Le Thi Thao Nguyen , Tran Quang De and Bui Thi Buu Hue

* Corresponding author (hhbvia2215@gmail.com)

Article Sidebar

Full Text: PDF

Received: 03 Jun 2019
Revised: 19 Jun 2019
Accepted: 30 Oct 2019
Published: 30 Oct 2019
Title: Synthesis and cytotoxicity evaluation of chalcone derivatives
DOI: 10.22144/ctu.jvn.2019.126
Views
327
Downloads
146
Crossref
Scopus
Google Scholar
Europe PMC
How to Cite
Bằng, H. H., Nguyên, L. T. T., Đệ, T. Q., & Huê, B. T. B. (2019). Synthesis and cytotoxicity evaluation of chalcone derivatives. CTU Journal of Science, 55(5), 37-42. https://doi.org/10.22144/ctu.jvn.2019.126
Issue
Vol. 55 No. 5 (2019)
Section
Natural Sciences

Abstract

Chalcone derivatives exhibit a wide range of biological activities including: antimalarial, antiinflammatory, antibacterial and anticancer. In this study, a one step procedure for the synthesis of five chalcone derivatives 3A, 3B, 3D, 3E and 3F has been successfully developed with two new compounds (E)-3-(2,5-dimethoxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one (3E) and (E)-3-(pyridin-4-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (3F). The synthesis method was performed by Claisen-Schmidt condensation reaction between methyl ketone and aromatic aldehyde derivatives in the presence of NaOH as the catalyst in ethanol as the solvent. The obtained yields of 3A, 3B, 3D, 3E and 3F were 70%, 73%, 75%, 90% and 86%, respectively. The structures of these compounds were fully determined by FT-IR, MS, 1H-NMR and 13C-NMR spectroscopy methods. The cytotoxicity assay indicated that compounds 3E and 3F were the most active against Hep-G2 cell line with IC50 of 10,46±0,09 μg/mL and 6,82±0,21 μg/mL, respectively.
Keywords: Chalcone derivatives, Claisen‐Schmidt condensation, cytotoxicity

Tóm tắt

Các dẫn xuất chalcone có nhiều hoạt tính sinh học bao gồm: kháng sốt rét, kháng viêm, kháng khuẩn và kháng ung thư. Trong nghiên cứu này, quy trình một bước để tổng hợp 5 dẫn xuất chalcone 3A, 3B, 3D, 3E và 3F đã được thực hiện thành công, trong đó có 2 hợp chất mới là (E)-3-(2,5-dimethoxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one (3E) và (E)-3-(pyridin-4-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (3F). Phương pháp tổng hợp được thực hiện bằng phản ứng ngưng tụ Claisen-Schmidt giữa các dẫn xuất methyl ketone và aldehyde thơm với sự hiện diện của xúc tác NaOH trong dung môi ethanol. Hiệu suất tổng hợp các dẫn xuất 3A, 3B, 3D, 3E và 3F đạt được lần lượt là 70%, 73%, 75%, 90% và 86%. Cấu trúc của các hợp chất được xác định dựa trên các dữ liệu phổ nghiệm bao gồm FT-IR, MS, 1H-NMR và 13C-NMR. Kết quả thử nghiệm độc tính với tế bào ung thư cho thấy hợp chất 3E và 3F có hoạt tính tốt nhất đối với dòng tế bào Hep-G2 với giá trị IC50 tương ứng là 10,46±0,09 μg/mL và 6,82± 0,21 μg/mL.
Từ khóa: dẫn xuất chalcone, độc tính tế bào, ngưng tụ Claisen‐Schmidt

Article Details

References

Bestman, H.J., and Kratzer, O., 1965. New reactions of alkylidenephosphoranesand their preparative uses. Part I: The acid-base character of phosphonium salts and alkylidenephosphoranes. AngewandteChemieInternational Edition in English. 4(7): 583-587.

Bhatia, V.K., and Kagan, J., 1970. A photochemical synthesis of2´,6´-dihydroxy-4´-methoxy and2´,4´-dihydroxy-6´-methoxychalcones. Chemistry & Industry. (37): 1203.

Budhiraja, A., Kadian, K., Kaur, M., et al., 2012. Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents. Medicinal Chemistry Research. 21(9): 2133-2140.

Bùi Thị Bửu Huê, 2010. Cơ chế phản ứng hữu cơ. NXB Đại học Cần Thơ, 132 trang.

Christov, R., Boryana, T.B., Popova, M., Bankova, V., and Bertrand, M., 2006. Chemical composition ofPropolis fromCanada, its antiradical activity and plant origin. Natural Product Research. 20(6): 531-536.

Lahtchev, K.L., Batovska, D.I., Parushev, S.P., Ubiyvovk, V.M., and Sibirny, A.A., 2008. Antifungal activity of chalcones: A mechanistic study using various yeast strains. European Journal of Medicinal Chemistry. 43(10): 2220-2228.

Liaras, K., Geronikaki, A., Glamoclija, J., Ciric, A., and Sokovic, M., 2011. Novel (E)-1-(4-methyl-2-(alkylamino)thiazol-5-yl)-3-arylprop-2-en-1-one as potent antimicrobial agents. Bioorganic &Medicinal Chemistry. 19(24): 7349-7356.

Mai, C.W., Yaeghoobi, M., Abd-Rahman, N., Kang, Y.B., and Pichika, M.R., 2014. Chalcones with electron-withdrawing and electron-donating substituents: anticancer activity againstTRAIL resistant cancer cells, structure-activity relationship analysis and regulation of apoptotic protein. European Journal of Medicinal Chemistry. 77: 378-387.

Normant, H., and Mantione, R., 1964. Preparation daldehydes et de cetones alpha-ethyleniques par isomerisation dethers alpha-acetyleniques. Comptes rendus hebdomadaires des seances de l academie des sciences. 259(9): 1635.

Phrutıvorapongkul, A., Lıpıpun, V., Ruangrungsı, N., et al., 2003. Studies on the chemical constituents of stem bark ofMillettia leucantha: isolation of new chalcones with cytotoxic, anti-herpes simplex virus and anti-inflammatory activities. Chemical and Pharmaceutical Bulletin. 51(2): 187-190.

Suwito, H., Jumina, J., Mustofa, M., Nimatuzahroh, N., and Puspaningsih, N.N.T., 2015. Anticancer and antimicrobial activity of methoxy amino chalcone derivatives. Pharmaceutical Chemistry. 7(3): 89-94.

Ullah, A., Ansari, F.L., Haq, I., Nazira, S., and Mirza, B., 2007. Combinatorial synthesis, lead identification, and antitumor study of a chalcone-based positional scanning library. Chemistry & Biodiversity. 4(2): 203-214.

Vasconcelos, A., Campos, V.F., Nedel, F., et al., 2013. Cytotoxic and apoptotic effects of chalcone derivatives of2-acetyl thiophene on human colon adenocarcinoma cells. Cell Biochemistry and Function. 31(4): 289-297.

Zhang, J., Ji, F.J., Gu, Y., Zhang, X.Y., and Qiao, S.X., 2014. Chalcones derivatives as potent cell division cycle25B phosphatase inhibitors. Pharmacological Reports. 66(3): 515-519.