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2′-Aminoanalogues of the cruciferous phytoalexins spirobrassinin, 1-methoxyspirobrassinin and 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer properties
Tetrahedron ( IF 2.1 ) Pub Date : 2017-09-19 , DOI: 10.1016/j.tet.2017.09.033
Mariana Budovská , Viera Tischlerová , Ján Mojžiš , Marianna Harvanová , Oleksandr Kozlov , Taťána Gondová , Nataša Tomášková

A method for the synthesis of new 2′-aminoanalogues of spiroindoline phytoalexins is reported. 2′-Aminonalogues of spirobrassinin, 1-methoxyspirobrassinin and 2,2′-diamino analogues of 1-methoxyspirobrassinol methyl ether were prepared by substitution of the methylsulphanyl group on the dihydrothiazole ring of corresponding phytoalexins. Final products were obtained by heating the phytoalexins with aniline or substituted aniline in the absence of solvent at 120 or 140 °C. By replacement of the SCH3 moiety of (S)-(−)- or (R)-(+)-spirobrassinin, enantiomers of 2′-aminoanalogues of spirobrassinin were also synthesized. Determination of their enantiomeric compositions using HPLC with chiral stationary phase revealed partial enantiomeric enrichment. The occurence of a SIDA effect of our 2′-aminonalogue of spirobrassinin was evaluated by examination of a non-racemic mixture in non-polar C6D6. Complete enantioresolution and distinct signals for two enantiomers were observed for a number of 1H and 13C NMR resonances. New synthesized compounds were supplied for testing the antiproliferative effect on a panel of six human cancer cell lines. 2′-Aminoanalogue with CF3 functionality exhibited more significant inhibitory effects than natural phytoalexins spirobrassinin.



中文翻译:

十字花科植物抗毒素螺旋螺花青素,1-甲氧基螺花青素和1-甲氧基螺花青素甲基醚的2'-氨基类似物:合成和抗癌特性

报道了螺环二氢吲哚植物抗毒素新的2'-氨基类似物的合成方法。通过取代相应植物抗毒素的二氢噻唑环上的甲基硫磺酰基,制备了螺螺花青素,1-甲氧基螺花青素和2-甲氧基螺花青素甲基醚的2,2'-二氨基类似物的2'-氨基酸。在没有溶剂的情况下,将植物抗毒素与苯胺或取代的苯胺在120或140°C下加热,即可得到最终产品。通过更换SCH的3(的部分小号) - ( - ) -或(- [R)-(+)-螺油菜籽素,还合成了螺油菜籽素的2'-氨基类似物的对映体。用具有手性固定相的HPLC测定其对映体组成表明部分对映体富集。通过检查非极性C 6 D 6中的非消旋混合物,评估了我们螺旋螺素的2'-氨基类似物SIDA效应的发生。在多个1 H和13 C NMR共振中观察到两种对映体的完全对映体拆分和不同信号。提供了新的合成化合物,以测试其对一组六种人类癌细胞系的抗增殖作用。2'-氨基类似物与CF 3 功能性比天然植物抗毒素螺旋螺花青素具有更显着的抑制作用。

更新日期:2017-09-19
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