4-(tert-butoxycarbonyl)-1-(2-hydroxyphenyl)-2-piperazinone

• 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: 4-(tert-butoxycarbonyl)-1-(2-hydroxyphenyl)-2-piperazinone
• 英文别名: Tert-butyl 4-(2-hydroxyphenyl)-3-oxopiperazine-1-carboxylate
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: LCQQURNZQLPBDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(tert-butoxycarbonyl)-1-(2-hydroxyphenyl)-2-piperazinone 在 caesium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design and optimization of novel (2S,4S,5S)-5-amino-6-(2,2-dimethyl-5-oxo-4-phenylpiperazin-1-yl)-4-hydroxy-2-isopropylhexanamides as renin inhibitors

  摘要：

  Introduction of the 2,2-dimethyl-4-phenylpiperazin-5-one scaffold into the P-3-P-1 portion of the (2S,4S,5S)-5-amino-6-dialkylamino-4-hydroxy-2-isopropylhexanamide backbone dramatically increased the renin inhibitory activity without using the interaction to the S-3(sp) pocket. Compound 31 exhibited >10,000-fold selectivity over other human proteases, and 18.5% oral bioavailability in monkey. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.092
• 作为产物：
  描述：

  3-氧代-1-哌嗪羧酸叔丁酯 在 potassium phosphate 、 copper(l) iodide 、 palladium on activated charcoal 、 氢气 、 N,N'-二甲基乙二胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(tert-butoxycarbonyl)-1-(2-hydroxyphenyl)-2-piperazinone
  参考文献：
  名称：

  Design and optimization of novel (2S,4S,5S)-5-amino-6-(2,2-dimethyl-5-oxo-4-phenylpiperazin-1-yl)-4-hydroxy-2-isopropylhexanamides as renin inhibitors

  摘要：

  Introduction of the 2,2-dimethyl-4-phenylpiperazin-5-one scaffold into the P-3-P-1 portion of the (2S,4S,5S)-5-amino-6-dialkylamino-4-hydroxy-2-isopropylhexanamide backbone dramatically increased the renin inhibitory activity without using the interaction to the S-3(sp) pocket. Compound 31 exhibited >10,000-fold selectivity over other human proteases, and 18.5% oral bioavailability in monkey. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.092

文献信息

• Inhibitors of prenyl-protein transferase
  申请人：——

  公开号：US20020010184A1

  公开（公告）日：2002-01-24

  The present invention comprises piperazinone-containing compounds which inhibit prenyl-protein transferases, including famesyl-protein transferase and geranylgeranyl-protein transferase type I. Such therapeutic compounds are useful in the treatment of cancer.

  该发明涉及含有哌嗪酮类化合物，可抑制前列蛋白转移酶，包括法美基蛋白转移酶和戈楞基蛋白转移酶I型。这种治疗性化合物对癌症的治疗具有用处。
• US6103723A
  申请人：——

  公开号：US6103723A

  公开（公告）日：2000-08-15
• [EN] INHIBITORS OF PRENYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE LA PRENYLE PROTEINE TRANSFERASE
  申请人：MERCK & CO INC

  公开号：WO2001060368A1

  公开（公告）日：2001-08-23

  The present invention comprises piperazinone-containing compounds which inhibit prenyl-protein transferases, including farnesyl-protein transferase and geranylgeranyl-protein transferase type I. Such therapeutic compounds are useful in the treatment of cancer.
• [EN] INHIBITORS OF PRENYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE PRENYLE PROTEINE TRANSFERASES
  申请人：MERCK & CO INC

  公开号：WO2001060815A1

  公开（公告）日：2001-08-23

  The present invention comprises piperazinone-containing compounds, which may be useful as inhibitors of prenyl-protein transferases, including farnesyl-protein transferase and geranylgeranyl-protein transferase type I. Such therapeutic compounds are useful in the treatment of cancer.
• Design and optimization of novel (2S,4S,5S)-5-amino-6-(2,2-dimethyl-5-oxo-4-phenylpiperazin-1-yl)-4-hydroxy-2-isopropylhexanamides as renin inhibitors
  作者：Yuji Nakamura、Chie Sugita、Masaki Meguro、Shojiro Miyazaki、Kazuhiko Tamaki、Mizuki Takahashi、Yoko Nagai、Takahiro Nagayama、Mikio Kato、Hiroshi Suemune、Takahide Nishi

  DOI：10.1016/j.bmcl.2012.05.092

  日期：2012.7

  Introduction of the 2,2-dimethyl-4-phenylpiperazin-5-one scaffold into the P-3-P-1 portion of the (2S,4S,5S)-5-amino-6-dialkylamino-4-hydroxy-2-isopropylhexanamide backbone dramatically increased the renin inhibitory activity without using the interaction to the S-3(sp) pocket. Compound 31 exhibited >10,000-fold selectivity over other human proteases, and 18.5% oral bioavailability in monkey. (C) 2012 Elsevier Ltd. All rights reserved.