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Recent advances in synthesis and biological activity of triterpenic acylated oximes.
Phytochemistry Reviews ( IF 7.7 ) Pub Date : 2015-04-11 , DOI: 10.1007/s11101-014-9353-5
Barbara Bednarczyk-Cwynar 1 , Lucjusz Zaprutko 1
Affiliation  

During the last few decades more and more attention has been paid to triterpenes-a group of compounds with five- or four-ring skeleton and carboxyl, hydroxyl or oxo groups. Triterpenes with unsubstituted C-3 hydroxyl group can be easily transformed into appropriate ketones and then into oximes. The carbonyl group can be created not only from the hydroxyl group at C-3 position, but also at C-2, C-12 or C-28 positions. Several methods of creation of two = NOH groups within one molecule of triterpene are known. There are also known triterpenes with two carbonyl groups, e.g. at C-3 and C-11 positions, which differ in reactivity: among them only C-3 group can be transformed into oxime. A reactive hydroxyimine group can undergo the action of acylating agents, such as carboxylic acids or their derivatives, also the ones with significant pharmacological activity. Acyl derivatives of triterpenic oximes exhibit important pharmacological activity. The biological tests performed with the use of cell cultures inoculated with viruses showed inhibitory activity of some triterpenic acyloximes against type 1 HSV (H7N1), ECHO-6 and HIV-1 viruses. Another acylated oximes derived from triterpenes shown cytotoxic or antiproliferative activity against many lines of cancer cells. In many cases the pharmacological effects of the tested acyloxyiminotriterpenes were comparable to those of appropriate standard drugs. One of the newest application of acyl derivatives of triterpenic oximes is their ability to form organogels.

中文翻译:

三萜酰化肟的合成和生物活性的最新进展。

在过去的几十年中,三萜烯越来越受到关注,三萜烯是具有五环或四环骨架以及羧基,羟基或氧代基团的一组化合物。具有未取代的C-3羟基的三萜可以轻松转化为适当的酮,然后转化为肟。羰基不仅可以由C-3位的羟基产生,而且可以由C-2,C-12或C-28位的羟基产生。在三萜烯的一个分子内产生两个= NOH基团的几种方法是已知的。还已知具有两个羰基的三萜,例如在C-3和C-11位置,它们的反应性不同:在它们之中,仅C-3基团可以转化为肟。反应性羟基亚胺基可经历酰化剂(例如羧酸或其衍生物)的作用,也具有明显的药理活性。三萜肟的酰基衍生物表现出重要的药理活性。使用接种了病毒的细胞培养物进行的生物学测试显示,某些三萜类酰肟对1型HSV(H7N1),ECHO-6和HIV-1病毒具有抑制活性。衍生自三萜的另一种酰化肟对许多癌细胞系显示出细胞毒性或抗增殖活性。在许多情况下,所测试的酰氧基亚氨基三萜的药理作用与适当的标准药物相当。三萜烯肟的酰基衍生物的最新应用之一是它们形成有机凝胶的能力。使用接种了病毒的细胞培养物进行的生物学测试显示,某些三萜类酰肟对1型HSV(H7N1),ECHO-6和HIV-1病毒具有抑制活性。衍生自三萜的另一种酰化肟对许多癌细胞系显示出细胞毒性或抗增殖活性。在许多情况下,所测试的酰氧基亚氨基三萜的药理作用与适当的标准药物相当。三萜烯肟的酰基衍生物的最新应用之一是它们形成有机凝胶的能力。使用接种了病毒的细胞培养物进行的生物学测试显示,某些三萜类酰肟对1型HSV(H7N1),ECHO-6和HIV-1病毒具有抑制活性。衍生自三萜的另一种酰化肟对许多癌细胞系显示出细胞毒性或抗增殖活性。在许多情况下,所测试的酰氧基亚氨基三萜的药理作用与适当的标准药物相当。三萜烯肟的酰基衍生物的最新应用之一是它们形成有机凝胶的能力。在许多情况下,所测试的酰氧基亚氨基三萜的药理作用与适当的标准药物相当。三萜烯肟的酰基衍生物的最新应用之一是它们形成有机凝胶的能力。在许多情况下,所测试的酰氧基亚氨基三萜的药理作用与适当的标准药物相当。三萜烯肟的酰基衍生物的最新应用之一是它们形成有机凝胶的能力。
更新日期:2019-11-01
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