Synthesis and in vitro anti-tumor activity of new oxadiazole thioglycosides

被引：91

作者：

Abu-Zaied, M. A. ^{[1
]}

El-Telbani, E. M. ^{[1
]}

Elgemeie, G. H. ^{[2
]}

Nawwar, G. A. M. ^{[1
]}

机构：

[1] Natl Res Ctr, Green Chem Dept, Cairo 12622, Egypt

[2] Helwan Univ, Fac Sci, Dept Chem, Cairo, Egypt

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2011年 / 46卷 / 01期

关键词：

1,3,4-Oxadiazole; Thiogycosides; Tamoxifen; 5-Flurouracil; Anti-tumor activities; Toxicity; EFFICIENT SYNTHESIS; DIRECT ROUTE; DERIVATIVES; ACID;

D O I：

10.1016/j.ejmech.2010.11.008

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A facile, convenient and high yielding synthesis of novel thioglycosides incorporating 1,3,4-oxadiazole, triazole and or triazine moieties from readily available starting materials has been described. The key step of this protocol is the formation of 3-isobutyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3) via condensation between methyl iso-butyl ketone and phenylhydrazine followed by application of Vilsmeier-Haack reaction. 3 was converted either to 1,3,4-oxadiazole derivative or condensed with O-aminothiols to give the bases 8, 19 and 20 in good yields, respectively. The aglycons 8, 19, and 20 were coupled with different activated halosugars in the presence of basic medium. Pharmacological evaluation of compounds 8, 14, 16 and 22 in vitro against 2-cell lines MCF-7 (breast) and HEPG2 (liver) revealed them to possess high anti-tumor activities with IC50 values ranging from 2.67-20.25 (mu g/mL) for breast cell line (MCF-7) and 4.62-43.6 (mu g/mL) for liver cell line (HEPG2). None of the tested compounds exhibited any toxicity in doses up to 500 mg kg(-1) of the animal body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.

引用

页码：229 / 235

页数：7

共 33 条

[1] Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl]acetic acid derivatives [J].