dimethyl (E)-2-(2-methyl)pentenylbutenedioate | 679436-03-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (E)-2-(2-methyl)pentenylbutenedioate
• CAS: 679436-03-4
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: WRZRMFQBKXMREZ-CSKARUKUSA-N

物化性质

• 沸点：
  312.9±37.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl (E)-2-(2-methyl)pentenylbutenedioate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Synthesis and biological activity of isopentenyl diphosphate analogues

  摘要：

  A series of analogues of isopentenyl diphosphate (IPP) having a dicarboxylate moiety in place of the diphosphate were synthesized and investigated as inhibitors of undecaprenyl diphosphate (UPP) synthase and protein farnesyltransferase (PFTase). PFTase is involved in control of cell proliferation and is known to be inhibited by certain maleic acid derivatives bearing long alkyl substituents (greater than or equal to12 carbons, e.g., chaetomellic acid). UPP synthase is a potential target for antimicrobial agents and utilizes isopentenyl diphosphate (IPP) as a substrate. A number of dicarboxylate-containing IPP analogues were prepared in 2-5 steps from commercially available starting materials with good overall yield (20-78%). These syntheses involved the conjugate addition of an organocuprate to dimethyl acetylenedicarboxylate (DMAD) followed by basic ester hydrolysis. The E-pentenylbutanedioic acid 32 showed inhibition of UPP synthase with an IC50 of 135 muM. Compound 30 displays competitive inhibition of PFTase with a K-i of 287 muM. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.033
• 作为产物：
  描述：

  4-甲基-4-戊烯酸乙酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 碘 、 magnesium 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 dimethyl (E)-2-(2-methyl)pentenylbutenedioate
  参考文献：
  名称：

  Synthesis and biological activity of isopentenyl diphosphate analogues

  摘要：

  A series of analogues of isopentenyl diphosphate (IPP) having a dicarboxylate moiety in place of the diphosphate were synthesized and investigated as inhibitors of undecaprenyl diphosphate (UPP) synthase and protein farnesyltransferase (PFTase). PFTase is involved in control of cell proliferation and is known to be inhibited by certain maleic acid derivatives bearing long alkyl substituents (greater than or equal to12 carbons, e.g., chaetomellic acid). UPP synthase is a potential target for antimicrobial agents and utilizes isopentenyl diphosphate (IPP) as a substrate. A number of dicarboxylate-containing IPP analogues were prepared in 2-5 steps from commercially available starting materials with good overall yield (20-78%). These syntheses involved the conjugate addition of an organocuprate to dimethyl acetylenedicarboxylate (DMAD) followed by basic ester hydrolysis. The E-pentenylbutanedioic acid 32 showed inhibition of UPP synthase with an IC50 of 135 muM. Compound 30 displays competitive inhibition of PFTase with a K-i of 287 muM. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.033