Synthesis Methyl Nitrophenyl Acrylate and Cytotoxic Activity Test against P388 Leukemia Cells

https://doi.org/10.22146/ijc.21226

Teni Ernawati(1*), Zulfa Khoirunni’mah(2)

(1) Research Center for Chemistry - Indonesian Institute of Sciences (LIPI), Kawasan Puspiptek Serpong, Tangerang Selatan 15314
(2) Program Study Pharmacy-Faculty of Medicine and Health Sciences, Syarif Hidayatullah State Islamic University (UIN) Jakarta
(*) Corresponding Author

Abstract


Synthesis of methyl nitrophenyl acrylate via modification of methyl trans-cinnamate had been done to improve its biological activity. The reaction of methyl trans-cinnamate with nitrating agent gave methyl 3-(2-nitrophenyl)acrylate and methyl 3-(4-nitrophenyl)acrylate with an ortho/para ratio of 1:8. Its structure was confirmed with 1H-NMR, 13C-NMR, FTIR, GC-MS. Biological activity of methyl 3-(4-nitrophenyl)acrylate and methyl 3-(2-nitrophenyl)acrylate assays was performed on Cancer cells against P388 Murine Leukemia with IC50= 7.98 μg/mL, IC50 = 27.78 μg/mL.

Keywords


nitration; methyl trans-cinnamate; methyl 3-(2-nitrophenyl)acrylate; 3-(4-nitrophenyl)acrylate; P388 leukemia cells

Full Text:

Full Text Pdf


References

[1] Arnatt, C.K., and Zhang, Y., 2012, Tetrahedron Lett., 53(13), 1592–1594.

[2] Becker, F.F., and Banik, B.K., 1998, Bioorg. Med. Chem. Lett., 8(20), 2877–2880.

[3] Shokrolahi, A., Zali; A., and Keshavarz, M.H., 2007, Chin. Chem. Lett., 18(9), 1064–1066.

[4] Rajanna, K.C., Kumar, M.S., Venkanna, P., Ramgopal, S., and Venkateswarlu, M., 2011, Int. J. Org. Chem., 1, 250–256.

[5] Wang, P-C., Lu, M., Zhu, J., Song, Y-M., and Xiong, X-F., 2011, Catal. Commun., 14(1), 42–47.

[6] Nowrouzi, N., Mehranpour, A.M., Bashiri, E., and Shayan, Z., 2012, Tetrahedron Lett., 53(36), 4841–4842.

[7] Nowrouzi, N., and Jonaghani, M.Z., 2011, Tetrahedron Lett., 52(39), 5081–5082.

[8] Cheng, G., Duan, X., Qi, X., and Lu, C., 2008, Catal. Commun., 10(2), 201–204.

[9] Bougdid, L., Heynderickx, A., Delbaere, S., and Moustrou, C., 2007, Tetrahedron, 63(34), 8242–8249.

[10] Lu, Y., Li, Y., Zhang, R., Jin, K., and Duan, C., 2013, Tetrahedron, 69(45), 9422–9427.

[11] Xiao, H-P., and Zhu, L-G., 2006, Inorg. Chem. Commun., 9(11), 1125–1128.

[12] Mukhopadhyay, C., and Datta, A., 2008, Catal. Commun., 9(15), 2588–2592.

[13] Jacoway, J., Kumar, G.G.K.S.N., and Laali, K.K., 2012, Tetrahedron Lett., 53(50), 6782–6785.

[14] Qiao, K., Hagiwara, H., and Yokoyama, C., 2006, J. Mol. Catal. A: Chem., 246(1-2), 65–69.

[15] You, K., Jian, J., Xiao, H., Pingle Liu, Ai, Q., and Luo, H., 2012, Catal. Commun., 28, 174–178.

[16] Bhatia, S.P., Wellington, G.A., Cocchiara, J., Lalko, J., Letizia, C.S., and Api, A.M., 2007, Food Chem. Toxicol., 45(1), S113–S119.

[17] Huang Q.S., Zhu, Y.J., Li, H.L., Zhuang, J.X., Zhang, C.L., Zhou, J.J., Li, W.G., and Chen, Q.X., 2009, J. Agric. Food Chem., 57(6), 2565–2569.

[18] Chen, Y-Y., Lee, M-H., Hsu, C-C., Wei, C-L., and Tsai, Y-C., 2012, J. Agric. Food Chem., 60(4), 955–963.

[19] Gigante, B., Prazeres, A.O., Marcelo-Curto, M.J., Cornelis, A., and Laszlo, P., 1995, J. Org. Chem., 60(11), 3445–3447.

[20] Oxley, J.C., Smith, J.L., Moran, J.S., Canino, J.N., and Almog, J., 2008, Tetrahedron Lett., 49(28), 4449–4451.

[21] Patel, J.R., Choubisa, B., and Dholakiya, B.Z., 2011, Chem. Sci. J., 33, 1–16.

[22] Dreger, K.W., and Pedersen, S.F., 2002, Solvent Purification in Academic Research Laboratories: A Comparison of Old and New Technologies, Presentation, AIHCE Laboratory Health & Safety Committee



DOI: https://doi.org/10.22146/ijc.21226

Article Metrics

Abstract views : 1233 | views : 1588


Copyright (c) 2015 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.