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

doi:10.1016/j.ejmech.2014.10.015

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

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 language	English
Pages (from-to)	805-813
Number of pages	9
Journal	European Journal of Medicinal Chemistry
Volume	87
DOIs	https://doi.org/10.1016/j.ejmech.2014.10.015
Publication status	Published - 24 Nov 2014

Keywords

oxadiazolines
naphthalene
synthesis
anticancer activity
Naphthalenes

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Chaaban, I., El Khawass, E. S. M., Abd El Razik, H. A., El Salamouni, N. S., Redondo-Horcajo, M., Barasoain, I., Díaz, J. F., Yli-Kauhaluoma, J., & Moreira, V. M. (2014). Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents. European Journal of Medicinal Chemistry, 87, 805-813. https://doi.org/10.1016/j.ejmech.2014.10.015

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title = "Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents",

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.",

keywords = "oxadiazolines, naphthalene, synthesis, anticancer activity, Naphthalenes",

author = "Ibrahim Chaaban and {El Khawass}, {El Sayeda M} and {Abd El Razik}, {Heba A} and {El Salamouni}, {Nehad S} and Mariano Redondo-Horcajo and Isabel Barasoain and D{\'i}az, {J Fernando} and Jari Yli-Kauhaluoma and Moreira, {V{\^a}nia M}",

year = "2014",

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doi = "10.1016/j.ejmech.2014.10.015",

language = "English",

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journal = "European Journal of Medicinal Chemistry",

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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

PY - 2014/11/24

Y1 - 2014/11/24

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.

KW - oxadiazolines

KW - naphthalene

KW - synthesis

KW - anticancer activity

KW - Naphthalenes

UR - http://www.sciencedirect.com/science/article/pii/S0223523414009416

U2 - 10.1016/j.ejmech.2014.10.015

DO - 10.1016/j.ejmech.2014.10.015

M3 - Article

C2 - 25440882

SN - 0223-5234

VL - 87

SP - 805

EP - 813

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

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

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Keywords

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