SYNTHESIS AND ANTICANCER ACTIVITY TEST OF 2-HYDROXY-N-PHENYLNICOTINAMIDE

https://doi.org/10.22146/ijc.21300

Salahuddin Salahuddin(1*), Muhammad Hanafi(2), Hariyanti Hariyanti(3)

(1) Faculty of Pharmacy, University of Uhamka, Perumnas Klender 13460, Jakarta
(2) Research Centre for Chemistry – LIPI, Kawasan Puspiptek, Tangerang 15314
(3) Faculty of Pharmacy, University of Pancasila, Lenteng Agung, Jakarta 12640
(*) Corresponding Author

Abstract


The novel compound of 2-hydroxy-N-phenylnicotinamide was synthesized from modification of the UK-3A compound, which was known biologically active to inhibit bacterial and cancer cells growth. Synthesis of this compound was carried out in one-step reaction. Analog UK-3A compound namely 2-hydroxy-N-phenylnicotinamide was synthesized from 2-hydroxynicotinic acid as the starting material using amidation reaction with aniline in presence of DCC/DMAP in pyridine. Analog UK-3A was analyzed and identified using TLC, FT-IR, LC-MS and FT-NMR spectrofotometer. The yield after purification was 42.97%. The IC50 value 85 μg/mL was obtained from cytotoxicity test against P388 Murine Leukemia cells. It indicated that the synthesis products were sufficiently potential for leukemia P388 treatment.

Keywords


2-hydroxy-N-phenylnicotinamide; UK-3A; Amidation; P388 Murine Leukemia cells

Full Text:

Full Text PDF


References

[1] Ueki, M., Kusumoto, A., Hanafi, M., Shibata, K., Tanaka, T., and Taniguchi, M., 1997, J. Antibiot., 50, 551–555.

[2] Hanafi, M., 1995, Studies of Novel Antibiotic Metabolites from Streptomyces Sp. 517-02, Department of Chemistry, Faculty of Science, Osaka City University

[3] Moutevelis-Minakakis, P., Papavassilopoulou, E., Michas, G., Georgikopoulou, K., Ragoussi, M-E., Neophytou, N., Zoumpoulakis, P., Mavromoustakos, T., and Hadjipavlou-Litina, D., 2011, Bioorg. Med. Chem., 19, 9, 2888–2902

[4] Marrero-Ponce, Y., Siverio-Mota, D., Gálvez-Llompart, M., Recio, M.C., Giner, R.M., García-Domènech, R., Torrens, F., Arán, V.J., Cordero-Maldonado, M.L., Esguera, C.V., de Witte, P.A., and Crawford, A.D., 2011, Eur. J. Med. Chem., 46, 12, 5736–5753.

[5] Tripodi, F., Pagliarin, R., Fumagalli, G., Bigi, A., Fusi, P., Orsini, F., Frattini, M., and Coccetti, P., 2012, J. Med. Chem., 55, 5, 2112–2124.

[6] Li, W-S.,Wang, C-H., Ko, S., Chang, T.T., Jen, Y.C., Yao, C-F., More, S.V., and Jao, S-C., 2012, J. Med. Chem., 55, 4, 1583–1592

[7] Parkin, D.M., Bray, F., Ferlay, J., and Pisani, P., 2005, CA Cancer J. Clin., 55, 2, 74–108

[8] Rajitha, C., Dubey, P.K., Sunku, V., Piedrafita, F.J., Veeramaneni, V.R., and Pal, M., 2011, Eur. J. Med. Chem., 46, 10, 4887–4896.

[9] Zhang, Y., Lv, Z., Zhong, H., Geng, D., Zhang, M., Zhang, T., Li, Y., Li, K., 2012, Eur. J. Med. Chem., 53, 356–363.

[10] Darmawan, A., Hanafi, M., and Anita, Y., 2008, Proceeding of the International Seminar on Chemistry, Jatinangor, 735–738.

[11] Arsianti, A., Hanafi, M., Saepudin, E., Morimoto, T., and Kakiuchi, K., 2010, Bioorg. Med. Chem. Lett., 20, 14, 4018–4020.

[12] Anita, Y., Hanafi, M., Putra, A.M.J., Arifin, S., Usuki, Y., and Lio, H., 2007, Indo. J. Chem., 7, 2, 214–217

[13] Usuki, Y., Adachi, N., Fujita, K-I., Ichimura, A., Lio, H., and Taniguchi, M., 2006, Bioorg. Med. Chem. Lett., 16, 12, 3319–3322.

[14] Sahidin, and Hakim, EH. 2006, Cytotoxic Properties of Oligostillbenoids from the Tree Barks of Hopea Dryobalamides. 60c, 723.

[15] Shimano, M., Kamei, N., Shibata, T., Inoguchi, K., Itoh, N., Ikari, T., and Senda, H. 1998. Tetrahedron, 54, 42, 12745–12774

[16] Arya, S., Kumar, N., Roy, P., and Sondhi, S.M., 2013, Eur. J. Med. Chem., 59, 7–14.



DOI: https://doi.org/10.22146/ijc.21300

Article Metrics

Abstract views : 1657 | views : 1605


Copyright (c) 2013 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 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

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