克氏烯菌素A核心结构的合成及其抗利什曼原虫活性
Synthesis and antileishmanial activity of the core structure of cristaxenicin A.
作者信息
Fumiyama Hitoshi, Sadayuki Tomoko, Osada Yasutaka, Goto Yasuyuki, Nakao Yoichi, Hosokawa Seijiro
机构信息
Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
Department of Animal Resource Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo, Tokyo 1138657, Japan.
出版信息
Bioorg Med Chem Lett. 2016 Sep 1;26(17):4355-7. doi: 10.1016/j.bmcl.2016.06.061. Epub 2016 Jul 7.
The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a β-alkoxy-α,β-unsaturated ketone. The nine membered ring possessing α,β-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC50 value of 2.4μM.
已合成了具有反式稠合二氢吡喃和九元环的克氏菌素A的核心结构，并对其抗利什曼原虫活性进行了评估。二氢吡喃环是通过不饱和醛与β-烷氧基-α,β-不饱和酮之间的[4+2]环加成反应合成的。具有α,β-不饱和醛的九元环是通过分子内NHK反应，然后进行光延重排构建的。克氏菌素A的外消旋核心结构的抗利什曼原虫活性评估的IC50值为2.4μM。
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