4-[2-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-ylcarbamoyl)ethyl]piperidine-1-carboxylic acid tert-butyl ester | 1449767-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[2-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-ylcarbamoyl)ethyl]piperidine-1-carboxylic acid tert-butyl ester
• CAS: 1449767-30-9
• 化学式: C₁₇H₂₇N₅O₃S
• 分子量: 381.499
• InChiKey: JYMBIBUIXBCHJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  89.35
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[2-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-ylcarbamoyl)ethyl]piperidine-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 24.0h， 以99%的产率得到N-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-3-piperidin-4-ylpropionamide hydrochloride
  参考文献：
  名称：

  Structure–Efficiency Relationship of [1,2,4]Triazol-3-ylamines as Novel Nicotinamide Isosteres that Inhibit Tankyrases

  摘要：

  Tankyrases 1 and 2 are members of the poly(ADP-ribose) polymerase (PARP) family of enzymes that modulate Wnt pathway signaling. While amide- and lactam-based nicotinamide mimetics that inhibit tankyrase activity, such as XAV939, are well-known, herein we report the discovery and evaluation of a novel nicotinamide isostere that demonstrates selectivity over,other PARP family members. We demonstrate the utilization of lipophilic efficiency-based structure efficiency relationships (SER) to rapidly drive the evaluation of this series. These efforts led to a series of selective, cell-active compounds with solubility, physicochemical, and in vitro properties suitable for further optimization.

  DOI：

  10.1021/jm400826j
• 作为产物：
  描述：

  3-amino-5,6-dihydro-thiazolo[2,3-c][1,2,4]triazole hydrobromide 、 1-N-BOC-4-哌啶丙酸 在 1-羟基苯并三唑 、 1,2-二氯乙烷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以26%的产率得到4-[2-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-ylcarbamoyl)ethyl]piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Structure–Efficiency Relationship of [1,2,4]Triazol-3-ylamines as Novel Nicotinamide Isosteres that Inhibit Tankyrases

  摘要：

  Tankyrases 1 and 2 are members of the poly(ADP-ribose) polymerase (PARP) family of enzymes that modulate Wnt pathway signaling. While amide- and lactam-based nicotinamide mimetics that inhibit tankyrase activity, such as XAV939, are well-known, herein we report the discovery and evaluation of a novel nicotinamide isostere that demonstrates selectivity over,other PARP family members. We demonstrate the utilization of lipophilic efficiency-based structure efficiency relationships (SER) to rapidly drive the evaluation of this series. These efforts led to a series of selective, cell-active compounds with solubility, physicochemical, and in vitro properties suitable for further optimization.

  DOI：

  10.1021/jm400826j