2-(Adamantan-1-ylamino)-1-[(R)-2-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-pyrrolidin-1-yl]-ethanone | 866554-82-7

• 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: 2-(Adamantan-1-ylamino)-1-[(R)-2-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-pyrrolidin-1-yl]-ethanone
• CAS: 866554-82-7
• 化学式: C₂₆H₄₁BN₂O₃
• 分子量: 440.434
• InChiKey: NWVSNLKMKQZQFJ-CLSRIUJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  50.8
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(Adamantan-1-ylamino)-1-[(R)-2-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-pyrrolidin-1-yl]-ethanone 在 盐酸 、 苯硼酸 作用下， 以 正己烷 为溶剂， 反应 16.0h， 以74%的产率得到N-(1-adamantyl)-Gly-boro-Pro
  参考文献：
  名称：

  Synthesis and structure–activity relationship of N-alkyl Gly-boro-Pro inhibitors of DPP4, FAP, and DPP7

  摘要：

  The structure-activity relationship of various N-alkyl Gly-boro-Pro derivatives against three dipeptidyl peptidases (DPPs) was studied. In a series of N'-cycloalkyl analogs, DPP4 and fibroblast activation protein-alpha (FAP) optimally preferred N-cycloheptyl whereas DPP7 tolerated even larger cycloalkyl rings. Gly alpha-carbon derivatization of N-cyclohexyl or N-(2-adamantyl) Gly-boro-Pro resulted in a significant decrease in potency against all the three DPPs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.075
• 作为产物：
  描述：

  (R)-2-吡咯烷硼酸蒎烷二醇酯盐酸盐 在 碳酸氢钠 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2-(Adamantan-1-ylamino)-1-[(R)-2-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-pyrrolidin-1-yl]-ethanone
  参考文献：
  名称：

  Synthesis and structure–activity relationship of N-alkyl Gly-boro-Pro inhibitors of DPP4, FAP, and DPP7

  摘要：

  The structure-activity relationship of various N-alkyl Gly-boro-Pro derivatives against three dipeptidyl peptidases (DPPs) was studied. In a series of N'-cycloalkyl analogs, DPP4 and fibroblast activation protein-alpha (FAP) optimally preferred N-cycloheptyl whereas DPP7 tolerated even larger cycloalkyl rings. Gly alpha-carbon derivatization of N-cyclohexyl or N-(2-adamantyl) Gly-boro-Pro resulted in a significant decrease in potency against all the three DPPs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.075