4-[(E)-2-[2-(2,4-dichlorophenyl)-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]pyrazol-3-yl]ethenyl]-2-methoxyphenol | 1028459-87-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-[(E)-2-[2-(2,4-dichlorophenyl)-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]pyrazol-3-yl]ethenyl]-2-methoxyphenol
• CAS: 1028459-87-1
• 化学式: C₂₇H₂₂Cl₂N₂O₄
• 分子量: 509.389
• InChiKey: NEPHGLUCGJHXGZ-BQYBEJQRSA-N

物化性质

• 沸点：
  683.7±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  姜黄素 、 2,4-二氯苯肼盐酸盐 以 溶剂黄146 为溶剂， 反应 8.0h， 以54%的产率得到4-[(E)-2-[2-(2,4-dichlorophenyl)-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]pyrazol-3-yl]ethenyl]-2-methoxyphenol
  参考文献：
  名称：

  Synthesis and exploration of novel curcumin analogues as anti-malarial agents

  摘要：

  Curcumin, a major yellow pigment and active component of turmeric, has been shown to possess anti-inflammatory and anti-cancer activities. Recent studies have indicated that curcumin inhibits chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) Plasmodium falciparum growth in culture with an IC50 of similar to 3.25 mu M (MIC = 13.2 mu M) and IC50 4.21 mu M (MIC = 14.4 mu M), respectively. In order to expand their potential as anti-malarials a series of novel curcumin derivatives were synthesized and evaluated for their ability to inhibit P. falciparum growth in culture. Several curcumin analogues examined show more effective inhibition of P. falciparum growth than curcumin. The most potent curcumin compounds 3, 6, and 11 were inhibitory for CQ-S P. falciparum at IC50 of 0.48, 0.87, 0.92 mu M and CQ-R P. falcipartan at IC50 of 0.45 mu M, 0.89, 0.75 mu M, respectively. Pyrazole analogue of curcumin (3) exhibited sevenfold higher anti-malarial potency against CQ-S and ninefold higher anti-malarial potency against CQ-R. Curcumin analogues described here represent a novel class of highly selective P. falcipartan inhibitors and promising candidates for the design of novel anti-malarial agents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.054

文献信息

• Synthesis and exploration of novel curcumin analogues as anti-malarial agents
  作者：Satyendra Mishra、Krishanpal Karmodiya、Namita Surolia、Avadhesha Surolia

  DOI：10.1016/j.bmc.2007.12.054

  日期：2008.3.15

  Curcumin, a major yellow pigment and active component of turmeric, has been shown to possess anti-inflammatory and anti-cancer activities. Recent studies have indicated that curcumin inhibits chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) Plasmodium falciparum growth in culture with an IC50 of similar to 3.25 mu M (MIC = 13.2 mu M) and IC50 4.21 mu M (MIC = 14.4 mu M), respectively. In order to expand their potential as anti-malarials a series of novel curcumin derivatives were synthesized and evaluated for their ability to inhibit P. falciparum growth in culture. Several curcumin analogues examined show more effective inhibition of P. falciparum growth than curcumin. The most potent curcumin compounds 3, 6, and 11 were inhibitory for CQ-S P. falciparum at IC50 of 0.48, 0.87, 0.92 mu M and CQ-R P. falcipartan at IC50 of 0.45 mu M, 0.89, 0.75 mu M, respectively. Pyrazole analogue of curcumin (3) exhibited sevenfold higher anti-malarial potency against CQ-S and ninefold higher anti-malarial potency against CQ-R. Curcumin analogues described here represent a novel class of highly selective P. falcipartan inhibitors and promising candidates for the design of novel anti-malarial agents. (C) 2007 Elsevier Ltd. All rights reserved.