3,4-Methylendioxycinnamoylpiperazin | 69113-94-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,4-Methylendioxycinnamoylpiperazin
• 英文别名: 1-(3-benzo[1,3]dioxol-5-yl-acryloyl)-piperazine；3-(1,3-Benzodioxol-5-yl)-1-piperazin-1-ylprop-2-en-1-one
• CAS: 69113-94-6
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: UMELPSILMBTLEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-Methylendioxycinnamoylpiperazin 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1

  摘要：

  Two "privileged fragments", caffeic acid and piperazine, were integrated into bevirimat producing new derivatives with improved activity against HIV-1/NL4-3 and NL4-3/V370A carrying the most prevalent bevirimat-resistant polymorphism. The activity of one of these, 18c, was increased by 3-fold against NL4-3 and 51-fold against NL4-3/V370A. Moreover, 18c is a maturation inhibitor with improved metabolic stability. Our study suggested that integration of privileged motifs into promising natural product skeletons is an effective strategy for discovering potent derivatives.

  DOI：

  10.1021/acs.jmedchem.6b00461
• 作为产物：
  描述：

  tert-butyl 4-[3-(1,3-benzodioxol-5-yl)prop-2-enoyl]piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以54%的产率得到3,4-Methylendioxycinnamoylpiperazin
  参考文献：
  名称：

  Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1

  摘要：

  Two "privileged fragments", caffeic acid and piperazine, were integrated into bevirimat producing new derivatives with improved activity against HIV-1/NL4-3 and NL4-3/V370A carrying the most prevalent bevirimat-resistant polymorphism. The activity of one of these, 18c, was increased by 3-fold against NL4-3 and 51-fold against NL4-3/V370A. Moreover, 18c is a maturation inhibitor with improved metabolic stability. Our study suggested that integration of privileged motifs into promising natural product skeletons is an effective strategy for discovering potent derivatives.

  DOI：

  10.1021/acs.jmedchem.6b00461

文献信息

• Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1
  作者：Yu Zhao、Qiong Gu、Susan L. Morris-Natschke、Chin-Ho Chen、Kuo-Hsiung Lee

  DOI：10.1021/acs.jmedchem.6b00461

  日期：2016.10.13

  Two "privileged fragments", caffeic acid and piperazine, were integrated into bevirimat producing new derivatives with improved activity against HIV-1/NL4-3 and NL4-3/V370A carrying the most prevalent bevirimat-resistant polymorphism. The activity of one of these, 18c, was increased by 3-fold against NL4-3 and 51-fold against NL4-3/V370A. Moreover, 18c is a maturation inhibitor with improved metabolic stability. Our study suggested that integration of privileged motifs into promising natural product skeletons is an effective strategy for discovering potent derivatives.