(1R,2S,3R,5S,6S)-3,5-diamino-7-oxaspiro[5.6]dodec-9-ene-1,2-diol | 1261084-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R,5S,6S)-3,5-diamino-7-oxaspiro[5.6]dodec-9-ene-1,2-diol
• 英文别名: (1S,3R,4S,5R,6S)-1,3-diamino-7-oxaspiro[5.6]dodec-9-ene-4,5-diol
• CAS: 1261084-78-9
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: XXQDSDDUNXRBHF-KJPMQGKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  benzyl ((1S,3R,4S,5R,6S)-3-amino-4,5-dihydroxy-7-oxaspiro[5.6]dodec-9-en-1-yl)carbamate 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以82%的产率得到(1R,2S,3R,5S,6S)-3,5-diamino-7-oxaspiro[5.6]dodec-9-ene-1,2-diol
  参考文献：
  名称：

  Second generation analogs of rigid 6,7-spiro scaffolds targeting the bacterial ribosome

  摘要：

  Previous work from our group described the synthesis and biological evaluation of new rigid, 6,6- and 6,7-spiro aminoglycosidic scaffolds targeting the bacterial ribosome. Herein we describe an improved synthetic protocol for their construction, and extend our study by further amino-functionalization of their 6,7-spiro analogs. The synthetic strategy, preparation and evaluation of some representative examples are reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.001

文献信息

• Designed Spiro-Bicyclic Analogues Targeting the Ribosomal Decoding Center
  作者：Thomas Cottin、Constantina Pyrkotis、Christos I. Stathakis、Ioannis Mavridis、Ioannis A. Katsoulis、Panoula Anastasopoulou、Georgia Kythreoti、Alexandros L. Zografos、Victoria R. Nahmias、Athanasios Papakyriakou、Dionisios Vourloumis

  DOI：10.1002/cbic.201000591

  日期：2011.1.3

  6‐bicyclic scaffolds that mimic many of the interactions of the natural aminoglycosides for the ribosomal decoding center. Their binding affinities for the A‐site along with their potential to inhibit protein production in vitro are presented. Our results comprise useful SAR observations for structure‐based drug design specific for RNA constructs.

  模仿氨基糖苷：已开发出一种优化的方法来合成刚性5,6，，6,6和7,6-双环支架，这些支架模仿了核糖体解码中心天然氨基糖苷的许多相互作用。介绍了它们对A位点的结合亲和力以及在体外抑制蛋白质生成的潜力。我们的结果包括针对RNA构建体的基于结构的药物设计的有用SAR观察结果。