4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-[4-(benzyloxy)benzyl]pyrimidin-2-amine | 198554-85-7

• 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]-6-[4-(benzyloxy)benzyl]pyrimidin-2-amine
• 英文别名: 2-Amino-4-(4-benzyloxyphenylmethyl)-6-[1-(3,4-methylenedioxybenzoyl)-4-piperidinyl]pyrimidine；[4-[2-amino-6-[(4-phenylmethoxyphenyl)methyl]pyrimidin-4-yl]piperidin-1-yl]-(1,3-benzodioxol-5-yl)methanone
• CAS: 198554-85-7
• 化学式: C₃₁H₃₀N₄O₄
• 分子量: 522.604
• InChiKey: XSSTVQAZRPDTGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-[4-(benzyloxy)benzyl]pyrimidin-2-amine 在 钯 碳酸氢钠 、 氯仿 、 甲醇 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 以to give the titled compound (256 mg) as a foam的产率得到4-({2-amino-6-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]pyrimidin-4-yl}methyl)phenol
  参考文献：
  名称：

  Piperidinylpyrimidine derivatives

  摘要：

  式（1）的化合物：##STR1## 其中，X.sup.1是氨基或羟基，X.sup.2是羰基等，R.sup.1是烷基、芳基等，R.sup.2是氢等，R.sup.3是烷基等，或其药学上可接受的盐，对于需要抑制肿瘤坏死因子的产生和/或分泌的患者具有有效作用。

  公开号：

  US05948786A1
• 作为产物：
  描述：

  碳酸胍 、 在 吡啶 作用下， 以425 mg的产率得到4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-[4-(benzyloxy)benzyl]pyrimidin-2-amine
  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

• [EN] PIPERIDINYLPYRAMIDINE DERIVATIVES<br/>[FR] DERIVES DE PIPERIDINYLPYRIMIDINE
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：WO1997038992A1

  公开（公告）日：1997-10-23

  (EN) A compound of formula (1) wherein; X1 is amino or hydroxyl, X2 is carbonyl and the like, R1 is an alkyl, an aryl and the like, R2 is hydrogen and the like, and R3 is an alkyl and the like, or a pharmaceutical acceptable salt thereof, is effective for inhibiting the production and/or secretion of tumor necrosis factor in a patient in need of such inhibition.(FR) L'invention concerne un composé de la formule (1) dans laquelle X1 représente amino ou hydroxyle, X2 représente carbonyle et analogue, R1 représente un alkyle, un aryle et analogue, R2 représente hydrogène et analogue, et R3 représente un alykle et analogue, ou un sel pharmaceutiquement acceptable de ce composé, ce dernier étant efficace pour inhiber la production et/ou la sécrétion du facteur de nécrose tumorale chez un patient nécessitant cette inhibition.

  化合物公式（1），其中：X1为氨基或羟基，X2为羰基等类似物，R1为烷基、芳基等类似物，R2为氢等类似物，R3为烷基等类似物，或其药用可接受盐，在需要抑制肿瘤坏死因子的患者中有效。
• Piperidinylpyrimidine derivatives
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US05948786A1

  公开（公告）日：1999-09-07

  A compound of formula (1) ##STR1## wherein X.sup.1 is amino or hydroxyl, X.sup.2 is carbonyl and the like R.sup.1 is an alkyl, an aryl and the like, R.sup.2 is hydrogen and the like, and R.sup.3 is an alkyl and the like, or a pharmaceutical acceptable salt thereof is effective for inibiting the production and/or secretion of tumor necrosis factor in a patient in need of such inhibition.

  式（1）的化合物：##STR1## 其中，X.sup.1是氨基或羟基，X.sup.2是羰基等，R.sup.1是烷基、芳基等，R.sup.2是氢等，R.sup.3是烷基等，或其药学上可接受的盐，对于需要抑制肿瘤坏死因子的产生和/或分泌的患者具有有效作用。
• PIPERIDINYLPYRAMIDINE DERIVATIVES
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0892795A1

  公开（公告）日：1999-01-27
• 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.