9-dihydroerythromycin B | 916243-06-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-dihydroerythromycin B
• CAS: 916243-06-6
• 化学式: C₃₉H₇₃NO₁₂
• 分子量: 748.008
• InChiKey: ZQWRFFMVBRYQTK-JTXHTSNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  52.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  176.84
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  9-dihydroerythromycin B 、 2-溴-N-甲基乙酰胺 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 2.17h， 生成 2-((2R,3S,4R,5R,6S,7R,9R,10R,11S,12S,13R)-10-((2S,3R,4S,6R)-4-(cyclobutyl(methyl)amino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-((2R,4R,5S,6S)-5-hydroxy-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：

  Structure−Activity Relationships of 9-Substituted-9-Dihydroerythromycin-Based Motilin Agonists: Optimizing for Potency and Safety

  摘要：

  A series of 9-dihydro-9-acetamido-N-desmethyl-N-isopropyl erythromycin A analogues and related derivatives was generated as motilin agonists. The compounds were optimized for potency while showing both minimal antibacterial activity and hERG inhibition. As the substituent on the amide was increased in lipophilicity the potency and hERG inhibition increased, while polar groups lowered potency, without significantly impacting hERG inhibition. The N-methyl acetamide 7a showed the optimal in vitro profile and was probed further by varying the chain length to the macrocycle as well as changing the macrocycle scaffold. 7a remained the compound with the best in vitro properties.

  DOI：

  10.1021/jm901107f
• 作为产物：
  描述：

  9-dihydro-N-desmethylerythromycin B 、 alkaline earth salt of/the/ methylsulfuric acid 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 9-dihydroerythromycin B
  参考文献：
  名称：

  9-Dihydroerythromycins as non-antibiotic motilin receptor agonists

  摘要：

  A series of 9-dihydroerythromycin A and B analogues with modification of the desosamine nitrogen have been synthesized and screened for motilin agonist activity, antibiotic activity, tachyphylaxis and hERG channel current inhibition. Small alkyl groups resulted in the potency while compounds with a primary or secondary amine resulted in the low motilin agonist potency. Several compounds were identified as non-antibiotic motilin receptor agonists with minimal tachyphylaxis and low hERG interaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.030