(R)-3-(benzyloxy)-2-(2-(2-chloro-4-(trifluoromethyl)phenoxy)nicotinamido)propanoic acid | 1239355-52-2

• 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: (R)-3-(benzyloxy)-2-(2-(2-chloro-4-(trifluoromethyl)phenoxy)nicotinamido)propanoic acid
• 英文别名: (2R)-2-[[2-[2-chloro-4-(trifluoromethyl)phenoxy]pyridine-3-carbonyl]amino]-3-phenylmethoxypropanoic acid
• CAS: 1239355-52-2
• 化学式: C₂₃H₁₈ClF₃N₂O₅
• 分子量: 494.855
• InChiKey: NGFBXSGSDXQBIK-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R)-3-(benzyloxy)-2-(2-(2-chloro-4-(trifluoromethyl)phenoxy)nicotinamido)propanoic acid 、 (S)-3-N-BOC-N-甲基氨基吡咯烷 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Discovery of a new class of glucosylceramide synthase inhibitors

  摘要：

  A novel series of potent inhibitors of glucosylceramide synthase are described. The optimization of biochemical and cellular potency as well as ADME properties led to compound 23c. Broad tissue distribution was obtained following oral administration to mice. Thus 23c could be another useful tool compound for studying the effects of GCS inhibition in vitro and in vivo. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.037
• 作为产物：
  描述：

  (2R)-O-benzylserine methyl ester 在 水 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 (R)-3-(benzyloxy)-2-(2-(2-chloro-4-(trifluoromethyl)phenoxy)nicotinamido)propanoic acid
  参考文献：
  名称：

  Discovery of a new class of glucosylceramide synthase inhibitors

  摘要：

  A novel series of potent inhibitors of glucosylceramide synthase are described. The optimization of biochemical and cellular potency as well as ADME properties led to compound 23c. Broad tissue distribution was obtained following oral administration to mice. Thus 23c could be another useful tool compound for studying the effects of GCS inhibition in vitro and in vivo. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.037

文献信息

• [EN] GLUCOSYLCERAMIDE SYNTHASE INHIBITORS<br/>[FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE
  申请人：EXELIXIS INC

  公开号：WO2010091104A8

  公开（公告）日：2011-04-07