[3-(4-Pyrimidin-2-yl-piperazin-1-yl)-propyl]-carbamic acid tert-butyl ester | 206053-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: [3-(4-Pyrimidin-2-yl-piperazin-1-yl)-propyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]carbamate
• CAS: 206053-35-2
• 化学式: C₁₆H₂₇N₅O₂
• mdl: MFCD24393194
• 分子量: 321.423
• InChiKey: SZVVEBPZLQRLGM-UHFFFAOYSA-N

物化性质

• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.687
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-(4-Pyrimidin-2-yl-piperazin-1-yl)-propyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到3-(4-嘧啶-2-哌嗪)-1-丙胺
  参考文献：
  名称：

  5-(5,6-Dichloro-2-indolyl)-2-methoxy-2,4-pentadienamides:  Novel and Selective Inhibitors of the Vacuolar H⁺-ATPase of Osteoclasts with Bone Antiresorptive Activity

  摘要：

  The vacuolar H+-ATPase (V-ATPase) located on the ruffled border of the osteoclast, is a proton pump which is responsible for secreting the massive amounts of protons that are required for the bone resorption process. With the aim to identify new agents which are able to prevent the excessive bone resorption associated with osteoporosis, we have designed a novel class of potent and selective inhibitors of the osteoclast proton pump, starting from the structure of the specific V-ATPase inhibitor bafilomycin A(1). Compounds 3a-d potently inhibited the V-ATPase in chicken osteoclast membranes (IC50 = 60-180 nM) and were able to prevent bone resorption by human osteoclasts in vitro at low-nanomolar concentrations. Notably, the EC50 of compound 3c in this assay was 45-fold lower than the concentration required for half-maximal inhibition of the V-ATPase from human kidney cortex. These results support the validity of the osteoclast proton pump as a useful molecular target to produce novel inhibitors of bone resorption, potentially useful as antiosteporotic agents.

  DOI：

  10.1021/jm9800144
• 作为产物：
  描述：

  1-(2-嘧啶基)哌嗪 、 N-Boc-3-氨基丙基溴 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以43%的产率得到[3-(4-Pyrimidin-2-yl-piperazin-1-yl)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  5-(5,6-Dichloro-2-indolyl)-2-methoxy-2,4-pentadienamides:  Novel and Selective Inhibitors of the Vacuolar H⁺-ATPase of Osteoclasts with Bone Antiresorptive Activity

  摘要：

  The vacuolar H+-ATPase (V-ATPase) located on the ruffled border of the osteoclast, is a proton pump which is responsible for secreting the massive amounts of protons that are required for the bone resorption process. With the aim to identify new agents which are able to prevent the excessive bone resorption associated with osteoporosis, we have designed a novel class of potent and selective inhibitors of the osteoclast proton pump, starting from the structure of the specific V-ATPase inhibitor bafilomycin A(1). Compounds 3a-d potently inhibited the V-ATPase in chicken osteoclast membranes (IC50 = 60-180 nM) and were able to prevent bone resorption by human osteoclasts in vitro at low-nanomolar concentrations. Notably, the EC50 of compound 3c in this assay was 45-fold lower than the concentration required for half-maximal inhibition of the V-ATPase from human kidney cortex. These results support the validity of the osteoclast proton pump as a useful molecular target to produce novel inhibitors of bone resorption, potentially useful as antiosteporotic agents.

  DOI：

  10.1021/jm9800144