基于2,6-二氧代双环[3.2.0]庚烷骨架构建异核苷。

Construction of an isonucleoside on a 2,6-dioxobicyclo[3.2.0]-heptane skeleton.

作者信息

Yoshimura Yuichi, Kobayashi Satoshi, Kaneko Hitomi, Suzuki Takeshi, Imamichi Tomozumi

机构信息

Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.

Laboratory of Human Retrovirology, Leidos Biochemical Research Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 21702, USA.

出版信息

Molecules. 2015 Mar 12;20(3):4623-34. doi: 10.3390/molecules20034623.

DOI:10.3390/molecules20034623

PMID:25774493

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6272333/

Abstract

We have built a new isonucleoside derivative on a 2,6-dioxobicyclo[3.2.0]heptane skeleton as a potential anti-HIV agent. To synthesize the target compound, an acetal-protected dihydroxyacetone was first converted to a 2,3-epoxy-tetrahydrofuran derivative. Introduction of an azide group, followed by the formation of an oxetane ring, gave a pseudosugar derivative with a 2,6-dioxobicyclo[3.2.0]heptane skeleton. The desired isonucleoside was obtained by constructing a purine base moiety on the scaffold, followed by amination.

摘要

我们在2,6-二氧代双环[3.2.0]庚烷骨架上构建了一种新的异核苷衍生物，作为一种潜在的抗HIV药物。为了合成目标化合物，首先将一个缩醛保护的二羟基丙酮转化为2,3-环氧四氢呋喃衍生物。引入一个叠氮基团，随后形成一个氧杂环丁烷环，得到了一种具有2,6-二氧代双环[3.2.0]庚烷骨架的假糖衍生物。通过在支架上构建嘌呤碱基部分，然后进行胺化反应，得到了所需的异核苷。