allyl-propyl-malonic acid | 868161-98-2

• 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: allyl-propyl-malonic acid
• 英文别名: Hepten-(1)-dicarbonsaeure-(4.4)；Allyl-propyl-malonsaeure；2-Allyl-2-propylmalonic acid；2-prop-2-enyl-2-propylpropanedioic acid
• CAS: 868161-98-2
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: CRYLXRKXSREUEA-UHFFFAOYSA-N

物化性质

• 沸点：
  106 °C(Press: 1.8e0 Torr)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  allyl-propyl-malonic acid 生成 2-丙基-4-五烯酸
  参考文献：
  名称：

  Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect

  摘要：

  In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant-activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds, These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (+/-)-4-methyl-2-n-propyl-4-pentenoic acid and (+/-)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.

  DOI：

  10.1021/tx950216s
• 作为产物：
  描述：

  丙基丙二酸二乙酯 在 氢氧化钾 、 sodium ethanolate 作用下， 以 乙醇 、 水 为溶剂， 生成 allyl-propyl-malonic acid
  参考文献：
  名称：

  Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect

  摘要：

  In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant-activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds, These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (+/-)-4-methyl-2-n-propyl-4-pentenoic acid and (+/-)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.

  DOI：

  10.1021/tx950216s

文献信息

• Hjelt, Chemische Berichte, 1896, vol. 29, p. 1857
  作者：Hjelt

  DOI：——

  日期：——
• Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect
  作者：Ursula Bojic、Mohamed M. A. Elmazar、Ralf-Siegbert Hauck、Heinz Nau

  DOI：10.1021/tx950216s

  日期：1996.1.1

  In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant-activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds, These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (+/-)-4-methyl-2-n-propyl-4-pentenoic acid and (+/-)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.