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D型和L型5'-氟-5'-脱氧-1',6'-异诺卡菌素的合成及其抗病毒活性,包括对埃博拉病毒的活性。

Synthesis of D-like and L-like 5'-fluoro-5'-deoxy-1',6'-isoneplanocins and their antiviral activity including Ebola.

作者信息

Liu Chong, Chen Qi, Schneller Stewart

机构信息

Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama, USA.

Department of Chemistry, Slippery Rock University, Slippery Rock, Pennsylvania, USA.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2020;39(1-3):342-348. doi: 10.1080/15257770.2019.1653466. Epub 2019 Aug 26.

Abstract

In exploring the 1',6'-isoneplanocin structural framework for antiviral compound development, both the D-like and L-like 5'-fluoro-5'-deoxy analogs have been synthesized from readily available cyclopentenyl iodides and adenine in five steps. Antiviral evaluation found D-like 5'-fluoro-5'-deoxy-1',6'-isoneplanocin to display less broad-spectrum antiviral effects than the parent D-like including weaker activity against Ebola and norovirus. The L-like enantiomer was devoid of any activity, contrary to the parent L-like compound.

摘要

在探索用于抗病毒化合物开发的1',6'-异片螺素结构框架时,已通过五个步骤从易得的环戊烯基碘化物和腺嘌呤合成了D型和L型5'-氟-5'-脱氧类似物。抗病毒评估发现,与母体D型相比,D型5'-氟-5'-脱氧-1',6'-异片螺素显示出较窄的广谱抗病毒作用,包括对埃博拉病毒和诺如病毒的活性较弱。与母体L型化合物相反,L型对映体没有任何活性。

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