Synthesis and an evaluation of the bioactivity of the C-glycoside of pseudopterosin A methyl ether
Synthesis and an evaluation of the bioactivity of the C-glycoside of pseudopterosin A methyl ether
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DOI：
10.1021/jo801432t
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发表时间：
2008-09-19
影响因子：
3.6
通讯作者：
Little, R. Daniel
中科院分区：
文献类型：
--
作者：
Zhong, Wei;Moya, Claudia;Little, R. Daniel
Suzuki-Miyaura 交叉偶联方案应用于 1a 的合成，1a 是 PsA 甲醚的 C-糖苷类似物。这标志着此类海洋天然产物首次构建C-糖苷，从而提供了将其生物活性与天然物质进行比较的机会。当测定其抗炎活性和抑制吞噬作用的能力时，其活性特征与 PsA (1) 和 PsA O-甲基醚 (1b) 相似。我们的结论是，当拟珊瑚素表达其抗炎和吞噬抑制特性时，就存在完整的结构，因此它们不太可能是前药。结果表明，1a 是 A(2A) 和 A(3) 腺苷受体的有效结合剂，IC50 值分别为 20 和 10 μM。
The Suzuki-Miyaura cross-coupling protocol was applied to the synthesis of 1a, the C-glycoside analogue of PsA methyl ether. This marks the first construction of a C-glycoside for this class of marine natural products, thereby offering an opportunity to compare its bioactivity to the natural substances. Its activity profile resembled that of PsA (1) and PsA O-methyl ether (1b) when assayed for its anti-inflammatory activity and its ability to inhibit phagocytosis. We conclude that the intact structure is present when a pseudopterosin expresses its anti-inflammatory and phagocytosis inhibitory properties and that they are, therefore, not likely to be prodrugs. Results show that 1a is an effective binding agent toward the A(2A) and A(3) adenosine receptors, displaying IC50 values of 20 and 10 mu M, respectively.