3'-乙酰氨基腺苷衍生物作为潜在A3腺苷受体激动剂的合成。
Synthesis of 3'-acetamidoadenosine derivatives as potential A3 adenosine receptor agonists.
作者信息
Chun Moon Woo, Choi Sung Wook, Kang Tae Kyung, Choi Won Jun, Kim Hea Ok, Gao Zhan-Guo, Jacobson Kenneth A, Jeong Lak Shin
机构信息
College of Pharmacy, Seoul National University, Seoul, Korea.
出版信息
Nucleosides Nucleotides Nucleic Acids. 2008 Apr;27(4):408-20. doi: 10.1080/15257770801944436.
Abstract
On the basis of high binding affinity of 3'-aminoadenosine derivatives 2b at the human A3 adenosine receptor (AR), 3'-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A3AR, our results revealed that 3'-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A3AR.
摘要
基于3'-氨基腺苷衍生物2b对人A3腺苷受体（AR）具有高结合亲和力，以1,2:5,6-二-O-异丙叉基-D-葡萄糖为原料，通过立体选择性硼氢化反应作为关键步骤合成了3'-乙酰氨基腺苷衍生物3a - e。尽管所有合成的化合物在人A3AR上完全没有结合亲和力，但我们的结果表明，在人A3AR的结合位点中，腺苷的3'-位仅能耐受像羟基或氨基这样的小尺寸氢键供体。
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