EFFECT OF BENZALDEHYDE EXCESS IN THE SYNTHESIS OF LR-2 AND CYTOTOXIC ACTIVITY OF LR-2 AGAINTS HeLa CELL
Abstract
LR-2(4-phenyl-3,4-dihydro-indeno[2’,1’]pyramidine-2(1H)- thione; Leni Ritmaleni 2), which designed and assumed to have biologically activity as anticancer, has been successfully synthesized by using the Biginelli reaction. This research was aimed to investigate the effect of benzaldehyde excess in the synthesis of LR-2 and to evaluate the cytotoxic activity of LR-2
against HeLa cancer cell lines. The synthesis was done by reacting benzaldehyde, 2-indanone and together with thiourea at one time as said as one pot reaction synthetic methodology and the reaction was acid catalysed. The mole equivalent of benzaldehyde was in excess compare to others. The effect of benzaldehyde in excess is the higher the mole of benzaldehyde, the lower the yield of LR-2. The cytotoxicity of LR-2 was done by using MTT method and the LC50 was 268.15 μM.
Key words : LR-2, benzaldehyde, cytotoxic, HeLa
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Atwal, K.S., Swanson, B.N., Unger, S.E., Floyd, D.M., Moreland, S., Hedberg, A. and O’Reilly, B.C., 1991, 3–Carbamoyl–4–aryl–1,2,3,4–tetrahydro–6–methyl–5–pyrimidinecarboxylic Acid Ester as Orally Effective Antihypersensive Agents. J. Med. Chem., 34, 806 – 811.
Bose, D.S., Fatima, L., and Merelaya, H.B., 2003, Green Chemistry Approaches to the Synthesis of 5–Alkoxycarbonyl–4–aryl–3, 4–dihydropyrimidin–2(1H)–ones by a Three–Component Coupling of One–Pot Condensation Reaction: Comparison of Ethanol, water, and Solvent–free Conditions. J. Org. Chem., 68, 587–590.
Kappe, C.O., 1993, 100 Years of the Biginelli dihydropyrimidine Synthesis, Tetrahedron, 49, 6937–6963.
Kappe, C.O., 1997, A Reexamination of the Mechanism of the Bigginelli dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate. J. Org. Chem., 62, 7201-7204.
Laksmiani, N. P., 2007, Uji Aktivitas Sitotoksik Senyawa 4-Fenil-3,4-dihidro-indeno [2′,1′]pirimidin-2(1H)-tion pada Sel Kanker HeLa dan Vero, Skripsi, Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta.
Maliga, Z. and Mitchison, T. J., 2006, Smallmolecule and mutational analysis of allosteric Eg5 inhibition by monastrol, BMC Chemical Biology , 6, 1472-6769
Mayer, T.U., Kapoor, T.M., Haggarty, R.W., King, S.I., Schreiber and Mitchinson, T. J., 1999, Small-Molecule Inhibitor of Mitotic Spindle Bipolarity Indentified in a Phenotype-Based Screen. Science., 286, 971-974.
Ritmaleni and Purwitasari, D., Sintesis LR-1 dengan variasi jenis katalis, Prosiding Seminar Nasional Farmasi, UNPAD, Bandung, 2009
Ritmaleni dan Kusuma, A. T., 2010., Pengaruh variasi jumlah mol 2-Indanon pada sintesis 4-Fenil-3,4-Dihidro Indeno[2’,1’] Pirimidin-2-On, Seminar Nasional Kimia, UNESA, Surabaya, prosiding,Ritmaleni dan Nurcahyani, W., 2006, Sintesis of 4-Fenil-3,4-tetrahidro-indeno[2,1]-pirimidin-2-on (LR-1), Majalah Farmasi Indonesia, 17, 3, 149-155
Ritmaleni dan Parmasari, M., 2011, Sintesis 4-fenil-3,4-Dihidro Indeno[2’,1’]Pirimidin-2-On (LR-1) dengan variasi jumlah katalis,eksakta, 12, 1, 12-16
Ritmaleni dan Sari. E., N., 2010, Pengaruh jumlah tiourea pada sintesis 4-fenil-3,4-Dihidro Indeno[2’,1’]Pirimidin-2-Tion (LR-2), Media Farmasi, 9, 1, 59-69
Ritmaleni, Anitasari, A., Susanti, S., Rumiyati dan Sismindari, 2011, Sintesis dan aktivitas sitotoksik LR-2 pada sel kanker payudara T47D, Majalah Farmasi Indonesia, 22, 1, 21-32
Russowsky, D., Lopes, F. A., and Da Silva, V. S. S. 2004, Multicomponent Biginelli’s Synthesis of 3,4- Dihydropyrimidin-2(1H)-ones promoted by Sn Cl2.2H2O, J. Braz.Chem. Soc.15, 2
Susanti S., 2007, Sintesis 4-Fenil-3,4-DihidroIndeno[2′,1′]Pirimidin-2[1H]-tion dan Uji Sitotoksisitas pada Kultur Sel Kanker Myeloma, Skripsi, Fakultas Farmasi Universitas Gadjah Mada, Yogyakarta.
Teng, W. Y., Yu, L. H., Chien, C. S., Ray, L. H., Ren, S. C. and Chien, C. C., 2005, Cytotoxic Acridone Alkaloids from the Stem Bark of Citrus Maxima, Journal of The Chinese Chemical Society, 52, 1253
DOI: http://dx.doi.org/10.14499/indonesianjpharm23iss1pp9-17
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