Russian Journal of General Chemistry

, Volume 88, Issue 11, pp 2388–2393 | Cite as

Synthesis and Cytotoxicity of 1,4-Naphthoquinone Oxime Derivatives

  • Q. Zhang
  • J. Dong
  • Q. Meng
  • G. Huang
  • S. Li


A series of hydroxylated 1,4-naphthoquinone oximes were designed and synthesized. The in vitro cytotoxicity of these compounds was evaluated against five human cancer cell lines and human skin fibroblast cell line. Among them, compounds (1E,4E)-6-{1-[(5-Hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8- dimethoxynaphthalene-1,4-dione dioxime and (1E,4E)-6-{1-[(6-Hydroxyhexyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione dioxime displayed higher cytotoxicity in three cancer cell lines than the positive drug 5-fluorouracil


naphthoquinone oxime cytotoxicity synthesis 


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  1. 1.
    Tandon, V.K. and Kumar, S., Expert Opin. Ther. Pat., 2013, vol. 23, p. 1087. doi 10.1517/13543776.2013.798303CrossRefGoogle Scholar
  2. 2.
    Prachayasittikul, V., Pingaew, R., Worachartcheewan, A., Nantasenamat, C., Prachayasittikul, S., Ruchirawat, S., and Prachayasittikul, V., Eur. J. Med. Chem., 2014, vol. 84, p. 247. doi 10.1016/j.ejmech.2014.07.024CrossRefGoogle Scholar
  3. 3.
    Wang, R., Zhang, X., Song, H., Zhou, S., and Li, S., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 4304. doi 10.1016/j.bmcl.2014.07.012CrossRefGoogle Scholar
  4. 4.
    Sánchez-Calvo, J.M., Barbero, G.R., Guerrero-Vásquez, G., Durán, A.G., Macías, M., Rodríguez-Iglesias, M.A., Molinillo, J.M.G., and Macías, F.A., Med. Chem. Res., 2016, vol. 25, p. 1274. doi 10.1007/s00044-016-1550-xCrossRefGoogle Scholar
  5. 5.
    Pingaew, R., Prachayasittikul, V., Worachartcheewan, A., Nantasenamat, C., Prachayasittikul, S., Ruchirawat, S., and Prachayasittikul, V., Eur. J. Med. Chem., 2015, vol. 103, p. 446. doi 10.1016/j.ejmech.2015.09.001CrossRefGoogle Scholar
  6. 6.
    Zhang, X., Wang, R.-B., Zhou, W., Xiao, S., Meng, Q.-Q., and Li, S.-S., AAPS PharmSciTech, 2015, vol. 16, p. 259, doi 10.1208/s12249-014-0217-5CrossRefGoogle Scholar
  7. 7.
    Huang, G., Zhao, H.-R., Zhou, W., Dong, J.-Y., Zhang, Q.-J., Meng, Q.-Q., Zhu, B.-Q., and Li, S.-S., Monatsh. Chem., 2017, vol. 148, p. 1011. doi 10.1007/s00706-016-1899-zCrossRefGoogle Scholar
  8. 8.
    Huang, G., Zhao, H., and Li, S., Russ. J. Gen. Chem., 2017, vol. 87, p. 2979. doi 10.1134/S1070363217120416CrossRefGoogle Scholar
  9. 9.
    Wang, R.-B., Zheng, X.-G., Zhou, W., Peng, Y., Zhu, M.-Y., and Li, S.-S., J. Chem. Res., 2010, vol. 34, p. 520. doi 10.3184/030823410X12843836823191CrossRefGoogle Scholar
  10. 10.
    Huang, G., Zhao, H.-R., Meng, Q.-Q., Zhou, W., Zhang, Q.-J., Dong, J.-Y., Cui, J.-H., and Li, S.-S., Chin. Chem. Lett., 2017, vol. 28, p. 1553. doi 10.1016/j.cclet.2016.10.034CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  1. 1.School of PharmacyShanghai Jiao Tong UniversityShanghaiChina

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