4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-2-chloro-6-(4-methoxybenzyl)pyrimidine | 1085916-73-9

• 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-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-2-chloro-6-(4-methoxybenzyl)pyrimidine
• 英文别名: 1,3-benzodioxol-5-yl-[4-[2-chloro-6-[(4-methoxyphenyl)methyl]pyrimidin-4-yl]piperidin-1-yl]methanone
• CAS: 1085916-73-9
• 化学式: C₂₅H₂₄ClN₃O₄
• 分子量: 465.936
• InChiKey: SFIPISOKLDFWCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-2-chloro-6-(4-methoxybenzyl)pyrimidine 在 10% Pd/C 、 氢气 、 sodium acetate 作用下， 以 甲醇 、 苯 为溶剂， 反应 8.0h， 以74%的产率得到4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidine
  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：

  4-[1-(1,3-苯并二噁唑-5-基羰基)哌啶-4-基]-6-(4-甲氧苄基)嘧啶-2-胺 在 亚硝酸特丁酯 、 三氯化锑 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以25%的产率得到4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-2-chloro-6-(4-methoxybenzyl)pyrimidine
  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.