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首页> 外文期刊>European Journal of Medicinal Chemistry: Chimie Therapeutique >Synthesis and in vitro anti-tumor activity of new oxadiazole thioglycosides.
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Synthesis and in vitro anti-tumor activity of new oxadiazole thioglycosides.

机译：新型恶二唑硫糖苷的合成及其体外抗肿瘤活性。

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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 IC(50) values ranging from 2.67-20.25 (mug/mL) for breast cell line (MCF-7) and 4.62-43.6 (mug/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.
机译：已经描述了从容易获得的原料中容易地，方便且高产率地合成掺入1，3，4-恶二唑，三唑和或三嗪部分的新型硫代糖苷。该方案的关键步骤是通过甲基异丁基酮与苯肼之间的缩合，然后进行Vilsmeier-Haack反应，形成3-异丁基-1-苯基-1H-吡唑-4-甲醛（3）。将3转化为1,3,4-恶二唑衍生物或与O-氨基硫醇缩合，分别以高收率得到碱8、19和20。在碱性培养基存在的情况下，将糖苷配基8、19和20与不同的活化金葡糖偶联。化合物8、14、16和22在体外针对2细胞系MCF-7（乳腺癌）和HEPG2（肝脏）的药理评估表明，它们具有较高的抗肿瘤活性，IC（50）值范围为2.67-20.25（对于乳腺癌细胞系（MCF-7）为杯子/ mL），对于肝细胞系（HEPG2）为4.62-43.6（杯子/ mL）。在最高500 mg kg（-1）动物体重的剂量下，所有测试化合物均未显示任何毒性。

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