(Z)-2-(2-methyl)butenylbutenedioic acid dicarbonic anhydride | 87453-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (Z)-2-(2-methyl)butenylbutenedioic acid dicarbonic anhydride
• 英文别名: 3-(3-Methylbut-3-enyl)furan-2,5-dione；3-(3-methylbut-3-enyl)furan-2,5-dione
• CAS: 87453-00-7
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: SRBLNAGPAZDLOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 (Z)-2-(2-methyl)butenylbutenedioic acid dicarbonic anhydride 以 甲苯 为溶剂， 反应 5.0h， 以54%的产率得到2-(3-methylbut-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarbonic anhydride
  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-溴-2-甲基-1-丁烯 在 盐酸 、 lithium hydroxide 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 (Z)-2-(2-methyl)butenylbutenedioic acid dicarbonic anhydride
  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

文献信息

• JPH06166773A
  申请人：——

  公开号：JPH06166773A

  公开（公告）日：1994-06-14
• Synthesis and biological activity of isopentenyl diphosphate analogues
  作者：A Scholte

  DOI：10.1016/j.bmc.2003.11.033

  日期：2004.2.15

  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.