(3R,4S,5S,6R,7R,9R,10S,11R,12R,13S,14R)-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-10-(1H-imidazol-5-ylmethoxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one | 1258846-59-1

• 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,11R,12R,13S,14R)-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-10-(1H-imidazol-5-ylmethoxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
• CAS: 1258846-59-1
• 化学式: C₄₃H₇₇N₃O₁₃
• 分子量: 844.097
• InChiKey: WYINVEQUECXPKR-GEPFGPCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  59
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  215
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  (9S)-9-dihydro-N-desmethyl-N-isopropylerythromycin A 、 4-氯甲基咪唑 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， 以46%的产率得到(3R,4S,5S,6R,7R,9R,10S,11R,12R,13S,14R)-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-10-(1H-imidazol-5-ylmethoxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
  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

• 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.