Synthesis and antiproliferative activity of goniobutenolides A and B, 5-halogenated crassalactone D derivatives and the corresponding 7-epimers

被引：4

作者：

Kovacevic, Ivana ^{[1
]}

Popsavin, Mirjana ^{[1
]}

Benedekovic, Goran ^{[1
]}

Kojic, Vesna ^{[2
]}

Jakimov, Dimitar ^{[2
]}

Rodic, Marko V. ^{[1
]}

Srdic-Rajic, Tatjana ^{[3
]}

Bogdanovic, Gordana ^{[2
]}

Divjakovic, Vladimir ^{[4
]}

Popsavin, Velimir ^{[1
]}

机构：

[1] Univ Novi Sad, Fac Sci, Dept Chem Biochem & Environm Protect, Trg Dositeja Obradovica 3, Novi Sad 21000, Serbia

[2] Oncol Inst Vojvodina, Put Doktora Goldmana 4, Sremska Kamenica 21204, Serbia

[3] Inst Oncol & Radiol Serbia, Pasterova 14, Belgrade 11000, Serbia

[4] Univ Novi Sad, Fac Sci, Dept Phys, Trg Dositeja Obradovica 4, Novi Sad 21000, Serbia

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2016年 / 108卷

关键词：

Goniobutenolide A; Goniobutenolide B; Crassalactone D; Haloetherification; Antitumour activity; Structure-activity relationships; Apoptosis; CYTOTOXIC STYRYL-LACTONES; APOPTOSIS; (+)-GONIOBUTENOLIDE; (+)-GONIOFUFURONE; STYRYLLACTONES; PROTEIN;

D O I：

10.1016/j.ejmech.2015.12.011

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new synthesis of goniobutenolides A (1) and B (2) and the corresponding 7-epimers has been achieved starting from diacetone D-glucose. The key step of the synthesis is a new one-pot sequence that commenced with Z-selective Wittig (or Horner-Wadsworth-Emmons) olefination, followed by successive gamma-lactonisation and beta-elimination. The above-mentioned unsaturated lactones were then converted to the corresponding 5-halogenated crassalactone D derivatives by using the appropriate haloetherification protocol. The most of synthesized compounds exhibited potent cytotoxic activities against a panel of tumour cell lines. The main structural features responsible for their antitumour potency have been revealed by means of SAR analysis. Flow cytometry data suggested that cytotoxic effects of these compounds in the culture of K562 cells might be mediated by apoptosis, additionally revealing that these molecules induced changes in cell cycle distribution of these cells. Results of semi-quantitative Western blot analysis indicate that the most of synthesized compounds induce apoptosis in a caspase-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.

引用

页码：594 / 604

页数：11

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