[(2R,3S,4S,5R,6S)-4-amino-6-[(1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3,5-dihydroxyoxan-2-yl]methyl 4-methylbenzenesulfonate | 1381860-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6S)-4-amino-6-[(1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3,5-dihydroxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 1381860-15-6
• 化学式: C₂₅H₄₂N₄O₁₃S
• 分子量: 638.693
• InChiKey: MDSZTZZGYKJPBL-MJOPLTPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  314
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  tetra-N-(tert-butoxycarbonyl)-kanamycin A 在 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 [(2R,3S,4S,5R,6S)-4-amino-6-[(1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3,5-dihydroxyoxan-2-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Amphiphilic aminoglycosides with increased selectivity for inhibition of connexin 43 (Cx43) hemichannels

  摘要：

  Gap junction channels formed by the association of connexin hemichannels play a crucial role in intercellular communication. Connexin 43 (Cx43) is expressed in a variety of tissues and organs, including heart and brain, and abnormal sustained opening of undocked "free" hemichannels contributes to the cell damage in cardiac infarcts and stroke. Selective inhibitors of Cx43 hemichannels for clinical use are then desirable. Here, we synthesized and tested new aminoglycosides for their connexin inhibitory activity towards Cx26 and Cx43 hemichannels. The lead compounds displayed enhanced Cx43/Cx26 selectivity for hemichannel inhibition when compared to the parent kanamycin A and other commercially available aminoglycosides. These lead compounds are not cytotoxic to mammalian cells and show promise for the treatment of ischemic damage of the heart, brain, and kidneys. We identified a new compound as a promising lead based on its good selectivity for Cx43 hemichannels inhibition and the simplicity and affordability of its production. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112602