(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-6-((2S,3R,4S,6R)-3-hydroxy-4-(isopropyl(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yloxy)-4-((2S,4S,6S)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one | 916243-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-6-((2S,3R,4S,6R)-3-hydroxy-4-(isopropyl(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yloxy)-4-((2S,4S,6S)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one
• 英文别名: (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl(propan-2-yl)amino]oxan-2-yl]oxy-4-[(2S,4S,6S)-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
• CAS: 916243-02-2
• 化学式: C₃₉H₇₃NO₁₂
• 分子量: 748.008
• InChiKey: VKWJDYXIDDVFQA-QVIWSPRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  177
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-6-((2S,3R,4S,6R)-3-hydroxy-4-(isopropyl(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yloxy)-4-((2S,4S,6S)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one 、 2-溴-N-甲基乙酰胺 在 potassium tert-butylate 作用下， 反应 4.0h， 生成 2-((2R,3S,4R,5R,6S,7R,9R,10R,11S,12S,13R)-2-ethyl-3,4,9-trihydroxy-10-((2S,3R,4S,6R)-3-hydroxy-4-(isopropyl(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yloxy)-12-((2S,4S,6S)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxooxacyclotetradecan-6-yloxy)-N-methylacetamide
  参考文献：
  名称：

  The role of the 4′′-hydroxyl on motilin agonist potency in the 9-dihydroerythromycin series

  摘要：

  The role of the erythromycin 4 ''-hydroxyl group has been explored on the motilin agonist potential in the 9-dihydroerythromycin series of motilides. The compounds show potencies 2- to 4-fold superior to the corresponding hydroxylated compounds. The relationship is maintained when the 9-hydroxyl is alkylated to generate the corresponding 4 ''-deoxy-9-O-acetamido-9-dihydroerythromycins. However, concomitant with this increase in potency is an increase in hERG inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.078
• 作为产物：
  描述：

  红霉素 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 碘 、 sodium acetate 、 二异丙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-6-((2S,3R,4S,6R)-3-hydroxy-4-(isopropyl(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yloxy)-4-((2S,4S,6S)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one
  参考文献：
  名称：

  The role of the 4′′-hydroxyl on motilin agonist potency in the 9-dihydroerythromycin series

  摘要：

  The role of the erythromycin 4 ''-hydroxyl group has been explored on the motilin agonist potential in the 9-dihydroerythromycin series of motilides. The compounds show potencies 2- to 4-fold superior to the corresponding hydroxylated compounds. The relationship is maintained when the 9-hydroxyl is alkylated to generate the corresponding 4 ''-deoxy-9-O-acetamido-9-dihydroerythromycins. However, concomitant with this increase in potency is an increase in hERG inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.078

文献信息

• The role of the 4′′-hydroxyl on motilin agonist potency in the 9-dihydroerythromycin series
  作者：Yaoquan Liu、Christopher W. Carreras、Mark Claypool、David C. Myles、Simon J. Shaw

  DOI：10.1016/j.bmcl.2011.04.078

  日期：2011.6

  The role of the erythromycin 4 ''-hydroxyl group has been explored on the motilin agonist potential in the 9-dihydroerythromycin series of motilides. The compounds show potencies 2- to 4-fold superior to the corresponding hydroxylated compounds. The relationship is maintained when the 9-hydroxyl is alkylated to generate the corresponding 4 ''-deoxy-9-O-acetamido-9-dihydroerythromycins. However, concomitant with this increase in potency is an increase in hERG inhibition. (C) 2011 Elsevier Ltd. All rights reserved.