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 | 198553-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 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
• 英文名称: 4-[1-(1,3-benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine
• 英文别名: [4-[2-Amino-6-[(4-methoxyphenyl)methyl]pyrimidin-4-yl]-1-piperidyl]-(1,3-benzodioxol-5-yl)methanone；[4-[2-amino-6-[(4-methoxyphenyl)methyl]pyrimidin-4-yl]piperidin-1-yl]-(1,3-benzodioxol-5-yl)methanone
• CAS: 198553-25-2
• 化学式: C₂₅H₂₆N₄O₄
• 分子量: 446.506
• InChiKey: XGABLOCLVRMQOH-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C(Solvent: Hexane)
• 沸点：
  710.6±70.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  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-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
• 作为产物：
  描述：

  1-苯甲酰哌啶-4-羧酸 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 potassium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 生成 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
  参考文献：
  名称：

  Synthesis and bioactivities of novel piperidylpyrimidine derivatives: inhibitors of tumor necrosis factor-alpha production

  摘要：

  New piperidylpyrimidine derivatives, including quinazolines, were prepared, and their abilities to inhibit TNF-alpha production evaluated. Some compounds showed potent inhibitory activity in mouse macrophages stimulated with LPS. The synthesis and structure-activity relationships of these compounds are described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00227-4

文献信息

• 慢性関節リウマチ治療剤
  申请人：——

  公开号：JP2003095951A

  公开（公告）日：2003-04-03

  (57)【要約】\n【課題】 慢性関節リウマチ治療剤、予防剤として有用な薬剤を提供する。\n【解決手段】 慢性関節リウマチ治療剤は、ピリミジン誘導体またはその薬学的に許容される塩を有効成分として含んでいる。該ピリミジン誘導体の一例としては、例えば、２−アミノ−４−〔１−（３，４−メチレンジオキシベンゾイル）−４−ピペリジニル〕−６−（４−メトキシフェニルメチル）ピリミジン\n【化１２】\nが挙げられる。

  (57) [摘要]n[主题]提供一种可作为慢性类风湿性关节炎治疗剂和预防剂的药剂。\慢性类风湿性关节炎治疗剂含有嘧啶衍生物或其药学上可接受的盐作为活性成分。嘧啶衍生物的一个例子是，例如，2-氨基-4-[1-(3,4-亚甲基二氧苯甲酰基)-4-哌啶基]-嘧啶衍生物。-哌啶基]-6-(4-甲氧基苯基甲基)嘧啶/n[12]Ϯn。
• Synthesis and bioactivities of novel piperidylpyrimidine derivatives: inhibitors of tumor necrosis factor-alpha production
  作者：Norio Fujiwara、Hitoshi Fujita、Kiyotaka Iwai、Ayumu Kurimoto、Shinobu Murata、Hajime Kawakami

  DOI：10.1016/s0960-894x(00)00227-4

  日期：2000.6

  New piperidylpyrimidine derivatives, including quinazolines, were prepared, and their abilities to inhibit TNF-alpha production evaluated. Some compounds showed potent inhibitory activity in mouse macrophages stimulated with LPS. The synthesis and structure-activity relationships of these compounds are described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.