(4a'R,6'S,7'R,8'R,8a'R)-7'-azido-6'-(((3aS,4R,6S,7R,7aS)-4,6-diazidohexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-7-yl)oxy)hexahydrospiro[cyclohexane-1,2'-pyrano[3,2-d][1,3]dioxin]-8'-yl trifluoromethanesulfonate | 918800-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4a'R,6'S,7'R,8'R,8a'R)-7'-azido-6'-(((3aS,4R,6S,7R,7aS)-4,6-diazidohexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-7-yl)oxy)hexahydrospiro[cyclohexane-1,2'-pyrano[3,2-d][1,3]dioxin]-8'-yl trifluoromethanesulfonate
• CAS: 918800-41-6
• 化学式: C₂₅H₃₄F₃N₉O₉S
• 分子量: 693.661
• InChiKey: HNFMCAQGVCOUQD-ROVWPPIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  47.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  245.03
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (4a'R,6'S,7'R,8'R,8a'R)-7'-azido-6'-(((3aS,4R,6S,7R,7aS)-4,6-diazidohexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-7-yl)oxy)hexahydrospiro[cyclohexane-1,2'-pyrano[3,2-d][1,3]dioxin]-8'-yl trifluoromethanesulfonate 在 sodium azide 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2R,3R,4S,6R)-4,6-Diazido-3-((2S,3R,4S,5S,6R)-3,4-diazido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol
  参考文献：
  名称：

  Redesign of aminoglycosides for treatment of human genetic diseases caused by premature stop mutations

  摘要：

  A series of new derivatives of the clinically used aminoglycoside antibiotic paromomycin were designed, synthesized, and their ability to read-through premature stop codon mutations was examined in both in vitro translation system and ex vivo mammalian cultured cells. One of these structures, a pseudo-trisaccharide derivative, showed notably higher stop codon read-through activity in cultured cells compared to those of paromomycin and gentamicin. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.013
• 作为产物：
  描述：

  1,3,2’-triazidoparomamine 在 camphor-10-sulfonic acid 吡啶 、 环己酮二甲缩酮 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.83h， 生成 (4a'R,6'S,7'R,8'R,8a'R)-7'-azido-6'-(((3aS,4R,6S,7R,7aS)-4,6-diazidohexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-7-yl)oxy)hexahydrospiro[cyclohexane-1,2'-pyrano[3,2-d][1,3]dioxin]-8'-yl trifluoromethanesulfonate
  参考文献：
  名称：

  WO2007/113841

  摘要：

  公开号：

文献信息

• Novel aminoglycosides and uses thereof in the treatment of genetic disorders
  申请人：Bassov Timor

  公开号：US20090093418A1

  公开（公告）日：2009-04-09

  A new class of paromomycin-derived aminoglycosides, which exhibit efficient stop-codon mutation suppression activity, low toxicity and high selectivity towards eukaryotic cells are provided. Also provided are chemical and chemo-enzymatic processes of preparing these paromomycin-derived aminoglycosides and intermediates thereof, as well as pharmaceutical compositions containing the same, and uses thereof in the treatment of genetic disorders.

  提供了一类新型的巴罗霉素衍生氨基糖苷类化合物，具有高效的终止密码子突变抑制活性、低毒性和高选择性作用于真核细胞。同时提供了制备这些巴罗霉素衍生氨基糖苷类化合物及其中间体的化学和化酶过程，以及含有它们的药物组合物，并在遗传疾病治疗中的应用。