(1R,11'S,15'R,16'S)-16'-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-7-methoxyspiro[naphthalene-1,12'-tetracyclo[8.6.0.03,8.011,15]hexadeca-1,3,5,7,9,13-hexaene]-2-one | 1158032-85-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1R,11'S,15'R,16'S)-16'-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-7-methoxyspiro[naphthalene-1,12'-tetracyclo[8.6.0.03,8.011,15]hexadeca-1,3,5,7,9,13-hexaene]-2-one
• CAS: 1158032-85-9
• 化学式: C₃₃H₃₃NO₆
• 分子量: 539.628
• InChiKey: JDIJVHOCLRRXFM-VWRKRVATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到(1R,11'S,15'R,16'S)-16'-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-7-methoxyspiro[naphthalene-1,12'-tetracyclo[8.6.0.03,8.011,15]hexadeca-1,3,5,7,9,13-hexaene]-2-one
  参考文献：
  名称：

  Designed DNA probes from the neocarzinostatin family: Impact of glycosyl linkage stereochemistry on bulge base binding

  摘要：

  Bulged sites in DNA and RNA have become targets for rational drug design due to their suspected involvement in a number of key biomolecular processes. A lead compound, derived from the enediyne natural product NCS-chrom has been used to inform chemical synthesis of a family of designed probes of DNA bulges, one of which shows 80 nM affinity for a two base bulged target. Key contributors to binding of these spirocyclic compounds have been studied in order to correlate affinity and specificity with structural features. Herein, we demonstrate that the glycosyl linkage stereochemistry of the pendant aminofucosyl group plays a pivotal role in binding, and coupled with insight obtained with various bulged targets, will allow rational design of second generation ligands. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.005