methyl (E)-2-[2-[(E)-3-bromopropenyl]phenyl]-3-methoxyacrylate | 262268-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (E)-2-[2-[(E)-3-bromopropenyl]phenyl]-3-methoxyacrylate
• 英文别名: methyl (E)-2-[2-[(E)-3-bromoprop-1-enyl]phenyl]-3-methoxyprop-2-enoate
• CAS: 262268-39-3
• 化学式: C₁₄H₁₅BrO₃
• 分子量: 311.175
• InChiKey: WWLHFEUOCJCFIM-XZUSAQEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-三氟甲基苯硫醇 、 methyl (E)-2-[2-[(E)-3-bromopropenyl]phenyl]-3-methoxyacrylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.34h， 以95%的产率得到(E)-3-Methoxy-2-{2-[(E)-3-(2-trifluoromethyl-phenylsulfanyl)-propenyl]-phenyl}-acrylic acid methyl ester
  参考文献：
  名称：

  Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore

  摘要：

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.

  DOI：

  10.1021/jm990002y
• 作为产物：
  描述：

  (E)-methyl 2-(2-bromophenyl)-3-methoxypropenoate 在 四(三苯基膦)钯 、 四溴化碳 、 对甲苯磺酸 、 三苯基膦 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 74.0h， 生成 methyl (E)-2-[2-[(E)-3-bromopropenyl]phenyl]-3-methoxyacrylate
  参考文献：
  名称：

  Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore

  摘要：

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.

  DOI：

  10.1021/jm990002y

文献信息

• Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore
  作者：Jawad Alzeer、Jacques Chollet、Ingrid Heinze-Krauss、Christian Hubschwerlen、Hugues Matile、Robert G. Ridley

  DOI：10.1021/jm990002y

  日期：2000.2.1

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.