Department of Image Science and Engineering, Pukyong National University, Busan 608 739, Republic of Korea.
Bioorg Med Chem Lett. 2010 Nov 15;20(22):6452-8. doi: 10.1016/j.bmcl.2010.09.079. Epub 2010 Sep 18.
A small library of diversely substituted 2,4,6,8-tetraaryl-3,7-diazabicyco[3.3.1]nonan-9-ones, their oximes and O-methyloximes were achieved in a stereocontrolled manner by an easiest synthetic strategy as single isomers with high yields. Stereochemistry of all the synthesized compounds was established by their 1D/2D NMR spectral studies, further, witnessed by single-crystal XRD analysis. Accordingly, the compounds exist in a chair-boat conformation with equatorial orientation of the substituents in the chair part and boat-axial orientation in the boat part. Finally, all the synthesized oximes and oxime ethers were evaluated for their in vitro antimicrobial activity against a panel of pathogenic bacteria and fungi, and as a result of the structure-activity correlations, some lead molecules were known for further optimization.
以一种最简便的合成策略，通过立体选择性方式，实现了多种取代的 2,4,6,8-四芳基-3,7-二氮杂双环[3.3.1]壬烷-9-酮、它们的肟和 O-甲肟的立体选择性库构建，得到了单一异构体，产率高。所有合成化合物的立体化学结构通过一维/二维 NMR 光谱研究得到确定，进一步通过单晶 XRD 分析得到证实。因此，这些化合物以椅船构象存在，取代基在椅部呈平伏取向，在船部呈船-轴向取向。最后，对所有合成的肟和肟醚进行了体外抗病原体细菌和真菌的抗菌活性评估，根据构效关系，确定了一些先导分子进行进一步优化。
