Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides
Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides
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N-邻苯二甲酰亚胺甲基2,3-二脱氧-和2,3-不饱和苷的合成及其抗炎活性
DOI：
10.1016/j.carres.2007.03.009
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发表时间：
2007-07-02
影响因子：
3.1
通讯作者：
Li, Zhong-Jun
中科院分区：
文献类型：
--
作者：
Meng, Xiang-Bao;Han, Dong;Li, Zhong-Jun
3，4，6-三-O-乙酰基-D-半乳糖醛、3，4，6-三-O-乙酰基-D-葡萄糖醛和3，6，2 '，3'，46 '-六-O-乙酰基-D-乳糖醛分别与N-羟甲基邻苯二甲酰亚胺和三氟化硼醚合物反应，通过Ferrier重排反应生成相应的邻苯二甲酰亚胺甲基不饱和糖苷。当使用半乳糖醛衍生物时，在经典的Ferrier条件下也分离出非Ferrier重排产物作为次要产物。邻苯二甲酰亚胺甲基脱氧糖苷容易通过氢化不饱和糖苷制备。在脱乙酰化后，对小鼠测试这些化合物的抗炎活性，发现三种化合物与氢化可的松琥珀酸钠（HSS）相比具有强效活性。(C)2007爱思唯尔有限公司保留所有权利。
3,4,6-Tri-O-acetyl-D -gal actal, 3,4,6-tri-O-acetyl-D-glucal and 3,6,2',3',46'-hexa-0-acetyl-D-lactaI were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivative was used, a non-Ferrier rearrangement product was also isolated as a minor product under classical Ferrier conditions. Phthalimidomethyl deoxy glycosides were readily prepared by hydrogenation of the unsaturated glycosides. Following deacetylation, the anti-inflammatory activities of these compounds were tested on mice and three were found to possess potent activity compared to hydrocortisone sodium succinate (HSS). (C) 2007 Elsevier Ltd. All rights reserved.