Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents

Ibrahim Chaaban, El Sayeda M El Khawass, Heba A Abd El Razik, Nehad S El Salamouni, Mariano Redondo-Horcajo, Isabel Barasoain, J Fernando Díaz, Jari Yli-Kauhaluoma, Vânia M Moreira

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Abstract

A series of new oxadiazoline-substituted naphthalenyl acetates 3a-e and oxadiazoline-substituted 4-methoxynaphthalenyl acetates 7b-e were synthesized and tested by the National Cancer Institute (NCI) for their in vitro anticancer activity. The two derivatives bearing acetoxy groups at the 1 and 3 positions of the phenyl ring 3c and 7c were the most active showing significant anticancer activity against all tested cancer cell lines, with GI50 values ranging from 0.175 to 3.91 μM, and 0.306-11.7 μM, respectively. The selectivity of compound 3c was greater for non-solid tumor cell lines. Computational prediction of molecular and pharmacokinetic properties revealed that both compounds are safe and compound 7c had a good drug-likeness score.

Original languageEnglish
Pages (from-to)805-813
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume87
DOIs
Publication statusPublished - 24 Nov 2014

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Keywords

  • oxadiazolines
  • naphthalene
  • synthesis
  • anticancer activity
  • Naphthalenes

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