Synthesis of N-methyl-4-piperidone Curcumin Analogues and Their Cytotoxicity Activity against T47D Cell Lines
Yum Eryanti(1*), Rudi Hendra(2), Tati Herlina(3), Adel Zamri(4), Unang Supratman(5)
(1) Laboratory of Synthesis Organic Chemistry, Department of Chemistry, Riau University, Pekanbaru 28293, Indonesia
(2) Laboratory of Synthesis Organic Chemistry, Department of Chemistry, Riau University, Pekanbaru 28293, Indonesia
(3) Laboratory of Organic Chemistry, Department of Chemistry, Padjadjaran University, Bandung, Indonesia
(4) Laboratory of Synthesis Organic Chemistry, Department of Chemistry, Riau University, Pekanbaru 28293, Indonesia
(5) Laboratory of Organic Chemistry, Department of Chemistry, Padjadjaran University, Bandung, Indonesia
(*) Corresponding Author
Abstract
Keywords
Full Text:
Full Text PDFReferences
[1] Rostom, S.A., Hassan, G.S., and El-Subbagh, H.I., 2009, Synthesis and biological evaluation of some polymethoxylated fused pyridine ring systems as antitumor agents, Arch. Pharm., 342 (10), 484–590.
[2] Dandia, A., Jain, A.K., and Sharma, S., 2012, An efficient and highly selective approach for the construction of novel dispiro heterocycles in guanidine-based task-specific [TMG][Ac] ionic liquid, Tetrahedron Lett., 53 (44), 5859–5863.
[3] Kumar, R.R., Perumal, S., Senthilkumar, P., Yogeeswari, P., and Sriram, D., 2007, An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles, Bioorg. Med. Chem. Lett., 17 (23), 6459–6462.
[4] Suzuki, M., Nakamura, T., Iyoki, S., Fujiwara, A., Watanabe, Y., Mohri, K., Isobe, K., Ono, K., and Yano, S., 2005, Elucidation of anti-allergic activities of curcumin-related compounds with a special reference to their anti-oxidative activities, Biol. Pharm. Bull., 28 (8) 1438–1443.
[5] Handler, N., Jaeger, W., Puschacher, H., Leisser, K., and Erker, T., 2007, Synthesis of novel curcumin analogues and their evaluation as selective cyclooxygenase-1 (COX-1) inhibitors, Chem. Pharm. Bull., 55 (1), 64–71.
[6] Yadav, B., Taurin, S., Rosengren, R.J., Schumacher, M., Diederich, M., Somers-Edgar, T.J., and Larsen, L., 2010, Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin, Bioorg. Med. Chem., 18 (18), 6701–6707.
[7] Wichitnithad, W., Nimmannit, U., Wacharasindhu, S., and Rojsitthisak, P., 2011, Synthesis, characterization and biological evaluation of succinate prodrugs of curcuminoids for colon cancer treatment, Molecules, 16 (2), 1888–1900.
[8] Subramaniam, D., Nicholes, N.D., Dhar, A., Umar, S., Awasthi, V., Welch, D.R., Jensen, R.A., and Anant, S., 2011, 3,5-bis(2,4-difluorobenzylidene)-4-piperidone, a novel compound that affects pancreatic cancer growth and angiogenesis, Mol. Cancer Ther., 10 (11), 2146–2156.
[9] Lagisetty, P., Powell, D.R., and Awasthi, V., 2009, Synthesis and structural determination of 3,5-bis(2-fluorobenzylidene)-4-piperidone analogs of curcumin, J. Mol. Struct., 936 (1-3), 23–28.
[10] Eryanti, Y., Herlina, T., Zamri, A., Halim, S.N.A., Shiono, Y., Syah, Y.M., Awang, K., and Supratman, U., 2014, 3,5-Bis(2-hydroxybenzylidene)piperidin-4-one, Molbank, M825, 1–3.
[11] Gregory, M., Dandavati, A., Lee, M., Tzou, S., Savagian, M., Brien, K.A., Satam, V., Patil, P., and Lee, M., 2013, Synthesis, cytotoxicity, and structure–activity insight of NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidones, Med. Chem. Res., 22 (11), 5588–5597.
[12] Mohamed, A.M., El-Sayed, W.A., Alsharari, M.A., Al-Qalawi, H.R., and Germoush, M.O., 2013, Anticancer activities of some newly synthesized pyrazole and pyrimidine derivatives, Arch. Pharm. Res., 36 (9),1055–1065.
[13] Das, U., Singh, R.S.P., Alcorn, J., Hickman, M.R., Sciotti, R.J., Leed, S.E., Lee, P.J., Roncal, N., and Dimmock, J.R., 2013, 3,5-Bis(benzylidene)-4-piperidones and related N-acyl analogs: A novel cluster of antimalarials targeting the liver stage of Plasmodium falciparum, Bioorg. Med. Chem., 21 (23), 7250–7256.
[14] Kelkel, M., Jacob, C., Dicato, M., and Diederich, M., 2010, Potential of the dietary antioxidants resveratrol and curcumin in prevention and treatment of hematologic malignancies, Molecules, 15, 7035–7074.
[15] Shimatsu, A., Kakeya, H., Imaizumi, A., Morimoto, T., Kanai, M., and Maeda, S., 2012, Clinical application of “curcumin”, a multi-functional substance, Anti-Aging Med., 9 (2), 75–83.
[16] Eryanti, Y., Zamri, A., Frimayanti, N., Supratman, U., and Herlina, T., 2016. Dataset of curcumin deivatives of QSAR modeling of anticancer against P388 cell line, Data Brief, 9, 573–578.
[17] Eryanti, Y., Zamri, A., Supratman, U., Herlina, T., Rosli, M.M., and Fun, H.K., 2015, Crystal structures of 3,5-bis[(E)-3-hydroxybenzylidene]-1-methylpiperidin-4-one and 3,5-bis[(E)-2-chlorobenzylidene]-1-methylpiperidin-4-one, Acta Cryst., E71,1488–1492.
[18] Alley, M.C., Scudiero, D.A., Monks, A., Hursey, M.L., Czerwinski, M.J., Fine, D.L., Abbott, B.J., Mayo, J.G., Shoemaker, R.H., and Boyd, M.R., 1988, Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay, Cancer Res., 48 (3), 589–601
DOI: https://doi.org/10.22146/ijc.24174
Article Metrics
Abstract views : 3505 | views : 3627Copyright (c) 2018 Indonesian Journal of Chemistry
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.
View The Statistics of Indones. J. Chem.