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

Research output: Contribution to journalArticle

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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.

LanguageEnglish
Pages805-813
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume87
DOIs
Publication statusPublished - 24 Nov 2014

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Antineoplastic Agents
Acetates
Bearings (structural)
Cells
Pharmacokinetics
National Cancer Institute (U.S.)
Tumor Cell Line
Tumors
Derivatives
Cell Line
Pharmaceutical Preparations
Neoplasms
In Vitro Techniques

Keywords

  • oxadiazolines
  • naphthalene
  • synthesis
  • anticancer activity
  • Naphthalenes

Cite this

Chaaban, Ibrahim ; El Khawass, El Sayeda M ; Abd El Razik, Heba A ; El Salamouni, Nehad S ; Redondo-Horcajo, Mariano ; Barasoain, Isabel ; Díaz, J Fernando ; Yli-Kauhaluoma, Jari ; Moreira, Vânia M. / Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents. In: European Journal of Medicinal Chemistry. 2014 ; Vol. 87. pp. 805-813.
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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.",
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Chaaban, I, El Khawass, ESM, Abd El Razik, HA, El Salamouni, NS, Redondo-Horcajo, M, Barasoain, I, Díaz, JF, Yli-Kauhaluoma, J & Moreira, VM 2014, 'Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents' European Journal of Medicinal Chemistry, vol. 87, pp. 805-813. https://doi.org/10.1016/j.ejmech.2014.10.015

Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents. / Chaaban, Ibrahim; El Khawass, El Sayeda M; Abd El Razik, Heba A; El Salamouni, Nehad S; Redondo-Horcajo, Mariano; Barasoain, Isabel; Díaz, J Fernando; Yli-Kauhaluoma, Jari; Moreira, Vânia M.

In: European Journal of Medicinal Chemistry, Vol. 87, 24.11.2014, p. 805-813.

Research output: Contribution to journalArticle

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T1 - Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents

AU - Chaaban, Ibrahim

AU - El Khawass, El Sayeda M

AU - Abd El Razik, Heba A

AU - El Salamouni, Nehad S

AU - Redondo-Horcajo, Mariano

AU - Barasoain, Isabel

AU - Díaz, J Fernando

AU - Yli-Kauhaluoma, Jari

AU - Moreira, Vânia M

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N2 - 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.

AB - 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.

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