Petasin is a potential antitumor against human neuroblastoma cell SK-N-SH by inhibiting the ERK1/2 phosphorylation. In view of its great activity and new antiproliferative mechanisms, a series of petasin derivatives were designed and synthesized, which showed great antiproliferative activity. Among them compounds 1h and 1f were more effective against SK-N-SH cells than petasin with the IC50 values of 0.87 and 2.63 μM, respectively.
References
[1]
Berbegall, A.P., Villamon, E., Tadeo, I., Martinsson, T., Canete, A., Castel, V., Navarro, S. and Noguera, R. (2014) Neuroblastoma after Childhood: Prognostic Relevance of Segmental Chromosome Aberrations, ATRX Protein Status, and Immune Cell Infiltration. Neoplasia, 16, 471-480.
http://dx.doi.org/10.1016/j.neo.2014.05.012
[2]
Agarwala, S., Mandelia, A., Bakhshi, S., Srinivas, M., Bajpai, M., Gupta, A.K., Gupta, D.K. and Bhatnagar, V. (2014) Neuroblastoma: Outcome over a 14 Year Period from a Tertiary Care Referral Centre in India. Journal of Pediatric Surgery, 49, 1280-1285.
http://dx.doi.org/10.1016/j.jpedsurg.2014.03.017
[3]
Spix, C., Pastore, G., Sankila, R., Stiller, C.A. and Steliarova-Foucher, E. (2006) Neuroblastoma Incidence and Survival in European Children (1978-1997): Report from the Automated Childhood Cancer Information System Project. European Journal of Cancer, 42, 2081-2091.
http://dx.doi.org/10.1016/j.ejca.2006.05.008
[4]
Cheng, Y.F., Wang, C.F., Li, W.J., Lin, Q. and Zhang, Q. (2012) Antiproliferation Effects of Petasin on Human Neuroblastoma SK-N-SH Cells. Acta Neuropharmacologica, 1, 1-6.
[5]
Yi, W.-B., Zhu, Y.-W. and Cai, C. (2013) Fluorous 4-N,N-Dimethylaminopyridium Iodide: Recyclable Organocatalysts by Precipitation for Acylation Reaction at Room Temperature. Catalysis Communications, 41, 26-28.
http://dx.doi.org/10.1016/j.catcom.2013.06.031
[6]
Liu, Z., Ma, Q., Liu, Y. and Wang, Q. (2014) 4-(N,N-Dimethylamino)Pyridine Hydrochloride as a Recyclable Catalyst for Acylation of Inert Alcohols: Substrate Scope and Reaction Mechanism. Organic Letters, 16, 236-239.
http://dx.doi.org/10.1021/ol4030875
[7]
Ozaki, A., Sumita, K., Goto, K. and Matsumoto, A. (2013) Synthesis of Poly(Decahydro-2-Naphthyl Methacrylate)s with Different Geometric Structures and Effects of Side-Group Dynamics on Polymer Properties Investigated by Thermal and Dynamic Mechanical Analyses and DFT Calculations. Macromolecules, 46, 2941-2950.
http://dx.doi.org/10.1021/ma400254d
[8]
Vyas, D.J., Larionov, E., Besnard, C., Guenee, L. and Mazet, C. (2013) Isomerization of Terminal Epoxides by a [Pd-H] Catalyst: A Combined Experimental and Theoretical Mechanistic Study. Journal of the American Chemical Society, 135, 6177-6183.
http://dx.doi.org/10.1021/ja400325w
[9]
Hyun, M.Y., Kim, S.H., Song, Y.J., Lee, H.G., Jo, Y.D., Kim, J.H., Hwang, I.H., Noh, J.Y., Kang, J. and Kim, C. (2012) Terminal and Internal Olefin Epoxidation with Cobalt(II) as the Catalyst: Evidence for an Active Oxidant Co(II)-Acylperoxo Species. The Journal of Organic Chemistry, 77, 7307-7312.
http://dx.doi.org/10.1021/jo3009963
[10]
Elbert, B.L., Lim, D.S., Gudmundsson, H.G., O’Hanlon, J.A. and Anderson, E.A. (2014) Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes. Chemistry, 20, 8594-8598.
http://dx.doi.org/10.1002/chem.201403255
[11]
Maury, J., Feray, L., Bertrand, M.P., Kapat, A. and Renaud, P. (2012) Unexpected Conversion of Alkyl Azides to Alkyl Iodides and of Aryl Azides to N-Tert-Butyl Anilines. Tetrahedron, 68, 9606-9611.
http://dx.doi.org/10.1016/j.tet.2012.09.066
[12]
Jurícek, M., Felici, M., Contreras-Carballada, P., Lauko, J., Bou, S.R., Kouwer, P.H.J., Brouwer, A.M. and Rowan, A.E. (2011) Triazole-Pyridine Ligands: A Novel Approach to Chromophoric Iridium Arrays. Journal of Materials Chemistry, 21, 2104-2111.
http://dx.doi.org/10.1039/C0JM03117H
[13]
Ogawa, S., Asada, M., Ooki, Y., Mori, M., Itoh, M. and Korenaga, T. (2005) Design and Synthesis of Glycosidase Inhibitor 5-Amino-1,2,3,4-cyclohexanetetrol Derivatives from (−)-Vibo-Quercitol. Bioorganic & Medicinal Chemistry, 13, 4306-4314.
http://dx.doi.org/10.1016/j.bmc.2005.04.003
[14]
Reed, C.S., Huigens III, R.W., Rogers, S.A. and Melander, C. (2010) Modulating the Development of E. coli Biofilms with 2-Aminoimidazoles. Bioorganic & Medicinal Chemistry Letters, 20, 6310-6312.
http://dx.doi.org/10.1016/j.bmcl.2010.08.075
[15]
Ma, L., Li, S., Zheng, H., Chen, J., Lin, L., Ye, X., Chen, Z., Xu, Q., Chen, T., Yang, J., Qiu, N., Wang, G., Peng, A., Ding, Y., Wei, Y. and Chen, L. (2011) Synthesis and Biological Activity of Novel Barbituric and Thiobarbituric Acid Derivatives against Non-Alcoholic Fatty Liver Disease. European Journal of Medicinal Chemistry, 46, 2003-2010.
http://dx.doi.org/10.1016/j.ejmech.2011.02.033
Zhou, L. and Lu, W. (2014) Palladium-Catalyzed Beta-Acyloxylation of Simple Amide via sp3 C-H Activation. Organic Letters, 16, 508-511.
http://dx.doi.org/10.1021/ol403393w
[18]
Jin, Y., Chen, S.W. and Tian, X. (2006) Synthesis and Biological Evaluation of New Spin-Labeled Derivatives of Podophyllotoxin. Bioorganic & Medicinal Chemistry, 14, 3062-3068.
http://dx.doi.org/10.1016/j.bmc.2005.12.025
[19]
Perez-Areales, F.J., Di Pietro, O., Espargaro, A., Vallverdu-Queralt, A., Galdeano, C., Ragusa, I.M., Viayna, E., Guillou, C., Clos, M.V., Perez, B., Sabate, R., Lamuela-Raventos, R.M., Luque, F.J. and Munoz-Torrero, D. (2014) Shogaol-Huprine Hybrids: Dual Antioxidant and Anticholinesterase Agents with β-Amyloid and Tau Anti-Aggregating Properties. Bioorganic & Medicinal Chemistry, 22, 5298-5307.
http://dx.doi.org/10.1016/j.bmc.2014.07.053
[20]
Kawano, H., Shakushiro, K., Nakata, M., Kita, A., Maeda, A., Watanabe, S., Sako, K. and Oku, N. (2014) Antitumor Efficacy and Biodistribution of Liposomal Sepantronium Bromide (YM155), a Novel Small-Molecule Survivin Suppressant. European Journal of Pharmaceutics and Biopharmaceutics, 88, 283-289.
http://dx.doi.org/10.1016/j.ejpb.2014.06.015
[21]
Rodriguez-Berna, G., Mangas-Sanjuan, V., Gonzalez-Alvarez, M., Gonzalez-Alvarez, I., Garcia-Gimenez, J.L., Diaz Cabanas, M.J., Bermejo, M. and Corma, A. (2014) A Promising Camptothecin Derivative: Semisynthesis, Antitumor Activity and Intestinal Permeability. European Journal of Medicinal Chemistry, 83, 366-373.
http://dx.doi.org/10.1016/j.ejmech.2014.06.050
[22]
Zhang, D., Debnath, B., Yu, S., Sanchez, T.W., Christ, F., Liu, Y., Debyser, Z., Neamati, N. and Zhao, G. (2014) Design and Discovery of 5-Hydroxy-6-Oxo-1,6-Dihydropyrimidine-4-Carboxamide Inhibitors of HIV-1 Integrase. Bioorganic & Medicinal Chemistry, 22, 5446-5453.
http://dx.doi.org/10.1016/j.bmc.2014.07.036
