ethyl 3-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-3-oxopropanoate | 198554-83-5

• 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: ethyl 3-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-3-oxopropanoate
• 英文别名: ethyl 3-[1-(1,3-benzodioxole-5-carbonyl)piperidin-4-yl]-3-oxopropanoate
• CAS: 198554-83-5
• 化学式: C₁₈H₂₁NO₆
• 分子量: 347.368
• InChiKey: PCSBQQUEJWAQDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-3-oxopropanoate 、 3-甲氧基苯基乙酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Novel piperidinylpyrimidine derivatives as inhibitors of HIV-1 LTR activation

  摘要：

  Piperidinylpyrimidine derivatives, previously prepared as inhibitors of TNF-alpha production, were evaluated for their inhibitory activity against HIV-1 LTR activation. Some of these derivatives inhibited activation of HIV-1 LTR-directed CAT gene expression induced by PMA in Jurkat cells. In this report, we describe SAR in this series of compounds and show that the 3,4-methylenedioxybenzoyl (piperonyloyl) group on the nitrogen of piperidine and lipophilic substitution at the C(6)-position of pyrimidine are important for this inhibitory activity. Some of the synthesized compounds also inhibited HIV-1 LTR transactivation induced by viral protein Tat. These results suggest that piperidinylpyrimidines are useful as potent AIDS therapeutics that directly inhibit HIV-1 LTR activation and indirectly suppress TNF-alpha production. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.059
• 作为产物：
  描述：

  1-(1,3-benzodioxol-5-ylcarbonyl)piperidine-4-carboxylic acid 、 magnesium bis(3-ethoxy-3-oxopropanoate) 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以96.1%的产率得到ethyl 3-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-3-oxopropanoate
  参考文献：
  名称：

  Novel piperidinylpyrimidine derivatives as inhibitors of HIV-1 LTR activation

  摘要：

  Piperidinylpyrimidine derivatives, previously prepared as inhibitors of TNF-alpha production, were evaluated for their inhibitory activity against HIV-1 LTR activation. Some of these derivatives inhibited activation of HIV-1 LTR-directed CAT gene expression induced by PMA in Jurkat cells. In this report, we describe SAR in this series of compounds and show that the 3,4-methylenedioxybenzoyl (piperonyloyl) group on the nitrogen of piperidine and lipophilic substitution at the C(6)-position of pyrimidine are important for this inhibitory activity. Some of the synthesized compounds also inhibited HIV-1 LTR transactivation induced by viral protein Tat. These results suggest that piperidinylpyrimidines are useful as potent AIDS therapeutics that directly inhibit HIV-1 LTR activation and indirectly suppress TNF-alpha production. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.059

文献信息

• Novel piperidinylpyrimidine derivatives as inhibitors of HIV-1 LTR activation
  作者：Norio Fujiwara、Takashi Nakajima、Yutaka Ueda、Hitoshi Fujita、Hajime Kawakami

  DOI：10.1016/j.bmc.2008.09.059

  日期：2008.11

  Piperidinylpyrimidine derivatives, previously prepared as inhibitors of TNF-alpha production, were evaluated for their inhibitory activity against HIV-1 LTR activation. Some of these derivatives inhibited activation of HIV-1 LTR-directed CAT gene expression induced by PMA in Jurkat cells. In this report, we describe SAR in this series of compounds and show that the 3,4-methylenedioxybenzoyl (piperonyloyl) group on the nitrogen of piperidine and lipophilic substitution at the C(6)-position of pyrimidine are important for this inhibitory activity. Some of the synthesized compounds also inhibited HIV-1 LTR transactivation induced by viral protein Tat. These results suggest that piperidinylpyrimidines are useful as potent AIDS therapeutics that directly inhibit HIV-1 LTR activation and indirectly suppress TNF-alpha production. (C) 2008 Elsevier Ltd. All rights reserved.