ethyl (2S,6S)-4-([(7-carbamoyl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methyl)-2,6-dimethyl-7-oxo-8-oxa-3,5-diaza-4-phosphadecan-1-oate 4-oxide | 1241052-16-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2S,6S)-4-([(7-carbamoyl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methyl)-2,6-dimethyl-7-oxo-8-oxa-3,5-diaza-4-phosphadecan-1-oate 4-oxide
• 英文别名: ethyl (2S)-2-[[(5-carbamoyl-4H-indeno[1,2-d][1,3]thiazol-8-yl)oxymethyl-[[(2S)-1-ethoxy-1-oxopropan-2-yl]amino]phosphoryl]amino]propanoate
• CAS: 1241052-16-3
• 化学式: C₂₂H₂₉N₄O₇PS
• 分子量: 524.535
• InChiKey: XJYTWLXHJNOVEU-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  187
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-[(bis([(1S)-2-ethoxy-1-methyl-2-oxoethyl]amino)phosphoryl)methoxy]-8H-indeno[1,2-d][1,3]thiazole-7-carboxylic acid 在 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以56%的产率得到ethyl (2S,6S)-4-([(7-carbamoyl-8H-indeno[1,2-d][1,3]thiazol-4-yl)oxy]methyl)-2,6-dimethyl-7-oxo-8-oxa-3,5-diaza-4-phosphadecan-1-oate 4-oxide
  参考文献：
  名称：

  Discovery of potent and orally active tricyclic-based FBPase inhibitors

  摘要：

  With the aim of exploring the effect of tricyclic-based FBPase inhibitors in cells and in vivo, a series of prodrugs of tricyclic phosphonates was designed and synthesized. Introducing prodrug moieties into tricyclic-based phosphonates led to the discovery of prodrug 15c, which strongly inhibited glucose production in monkey hepatocytes. Furthermore, prodrug 15c lowered blood glucose levels in fasted cynomolgus monkeys. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.041

文献信息

• Discovery of potent and orally active tricyclic-based FBPase inhibitors
  作者：Tomoharu Tsukada、Osamu Kanno、Takahiro Yamane、Jun Tanaka、Taishi Yoshida、Akira Okuno、Takeshi Shiiki、Mizuki Takahashi、Takahide Nishi

  DOI：10.1016/j.bmc.2010.05.041

  日期：2010.7

  With the aim of exploring the effect of tricyclic-based FBPase inhibitors in cells and in vivo, a series of prodrugs of tricyclic phosphonates was designed and synthesized. Introducing prodrug moieties into tricyclic-based phosphonates led to the discovery of prodrug 15c, which strongly inhibited glucose production in monkey hepatocytes. Furthermore, prodrug 15c lowered blood glucose levels in fasted cynomolgus monkeys. (C) 2010 Elsevier Ltd. All rights reserved.