9-dihydro-9-O-(2-aminoethyl)-N-desmethyl-N-isopropyl-hydroerythromycin A | 916242-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-dihydro-9-O-(2-aminoethyl)-N-desmethyl-N-isopropyl-hydroerythromycin A
• 英文别名: (3R,4S,5S,6R,7R,9R,10S,11R,12R,13S,14R)-10-(2-aminoethoxy)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl(propan-2-yl)amino]oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
• CAS: 916242-85-8
• 化学式: C₄₁H₇₈N₂O₁₃
• 分子量: 807.076
• InChiKey: JJJNJHAYAIWWIB-ACIZIVCMSA-N

物化性质

• 沸点：
  857.0±65.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  56
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  212
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  9-dihydro-9-O-(2-aminoethyl)-N-desmethyl-N-isopropyl-hydroerythromycin A 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以48%的产率得到N-[2-[[(2R,3S,4R,5R,6S,7R,9R,10R,11S,12S,13R)-2-ethyl-3,4,9-trihydroxy-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl(propan-2-yl)amino]oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]oxy]ethyl]-3H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Motilide compounds

  摘要：

  具有如公式（I）所示结构的化合物，其中RA、RB、RC、RD、RE和RF的定义如本文所述，可用作促动力剂。

  公开号：

  US20060270616A1
• 作为产物：
  描述：

  (9S)-9-dihydro-N-desmethyl-N-isopropylerythromycin A 、 2-溴乙胺氢溴酸盐 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以40%的产率得到9-dihydro-9-O-(2-aminoethyl)-N-desmethyl-N-isopropyl-hydroerythromycin A
  参考文献：
  名称：

  9-Dihydroerythromycin ethers as motilin agonists—Developing structure–activity relationships for potency and safety

  摘要：

  A series of derivatives of the amine of 9-dihydro-9-O-ethylamino-N-desmethyl-N-isopropyl erythromycin A derivatives were synthesized as motilin agonists. The compounds were developed for potency without showing antibacterial activity and inhibition of the hERG potassium channel. The formamide of the amide series was found to show the optimal combination of properties relative to carbamates, ureas, thioureas, and amines. This prompted an investigation of heterocyclic isosteres for the amide. In this series the triazole had the optimal combination of properties. From the study, two compounds met the criteria for detailed pharmacokinetic studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.035

文献信息

• MOTILIDE COMPOUNDS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1888082B1

  公开（公告）日：2012-09-12
• US7582611B2
  申请人：——

  公开号：US7582611B2

  公开（公告）日：2009-09-01
• Motilide compounds
  申请人：Liu Yaoquan

  公开号：US20060270616A1

  公开（公告）日：2006-11-30

  Compounds having a structure according to formula (I) where R A , R B , R C , R D , R E , and R F are as defined herein, are useful as prokinetic agents.

  具有如公式（I）所示结构的化合物，其中RA、RB、RC、RD、RE和RF的定义如本文所述，可用作促动力剂。
• 9-Dihydroerythromycin ethers as motilin agonists—Developing structure–activity relationships for potency and safety
  作者：Yaoquan Liu、Yong Li、David C. Myles、Mark Claypool、Christopher W. Carreras、Simon J. Shaw

  DOI：10.1016/j.bmc.2010.08.035

  日期：2010.11

  A series of derivatives of the amine of 9-dihydro-9-O-ethylamino-N-desmethyl-N-isopropyl erythromycin A derivatives were synthesized as motilin agonists. The compounds were developed for potency without showing antibacterial activity and inhibition of the hERG potassium channel. The formamide of the amide series was found to show the optimal combination of properties relative to carbamates, ureas, thioureas, and amines. This prompted an investigation of heterocyclic isosteres for the amide. In this series the triazole had the optimal combination of properties. From the study, two compounds met the criteria for detailed pharmacokinetic studies. (C) 2010 Elsevier Ltd. All rights reserved.