Isobutyl-4-yn-valproic acid | 176638-59-8

• 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: Isobutyl-4-yn-valproic acid
• 英文别名: 2-(2-Methylpropyl)pent-4-ynoic acid
• CAS: 176638-59-8
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: CIPDGBZQHUXNFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  isobutyl-prop-2-ynyl-malonic acid 生成 Isobutyl-4-yn-valproic 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

• Antiproliferative and neurotrophic molecules
  申请人：——

  公开号：US20020013367A1

  公开（公告）日：2002-01-31

  Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.

  提供了与抗癫痫药物丙戊酸钠有关的神经营养和抗增生化合物。这些化合物可用于促进神经元功能，如神经退行性疾病和治疗肿瘤性疾病。
• NEUROTROPHIC AND ANTIPROLIFERATIVE COMPOUNDS
  申请人：AMERICAN BIOGENETIC SCIENCES, INC.

  公开号：EP0778820A1

  公开（公告）日：1997-06-18
• US6300373B1
  申请人：——

  公开号：US6300373B1

  公开（公告）日：2001-10-09
• US6274624B1
  申请人：——

  公开号：US6274624B1

  公开（公告）日：2001-08-14
• [EN] NEUROTROPHIC AND ANTIPROLIFERATIVE COMPOUNDS<br/>[FR] COMPOSES NEUROTROPHIQUES ET ANTIPROLIFERATIFS
  申请人：——

  公开号：WO1996006821A1

  公开（公告）日：1996-03-07

  [EN] Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate of general formula (I), wherein R<1> is -CCH, -CH=CH2 or -CH2-CH3, R<2> is a saturated, unsaturated, branched or unbranched C1-C30 alkyl group which is optionally substituted with a C3-C9 aliphatic or aromatic cyclohydrocarbon,or heterocyclic group. M is a hydrogen or a metal atom. Formula (I) is not 2-n-propyl-4-pentynoic acid (4-yn-VPA) or 2-n-propyl-4-pentenoic acid (4-en-VPA) and when R<1> is -CH2-CH3, R<2> is C5 to C30. This invention also provides a method of making the compounds of the invention. The compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.
  [FR] L'invention concerne des composés neurotrophiques et antiprolifératifs, se rapportant à l'antiépileptique valproate, de formule générale (I), où R<1> représente -CCH, -CH=CH2 ou -CH2-CH3; R<2> représente un groupe alkyle C1-C30 saturé, non saturé, ramifié ou non; éventuellement substitué par un groupe C3-C9 d'hydrocarbure cyclique aromatique ou aliphatique, ou hétérocyclique; M représente un atome d'hydrogène ou de métal. La formule (I) n'est pas un acide 2-n-propyl-4-pentynoïque (4-yn-VPA) ni un acide 2-n-propyl-4-penténoïque (4-en-VPA) et lorsque R<1> représente -CH2-CH3, R<2> représente C5 à C30. L'invention concerne également un procédé de fabrication desdits composés. Ces composés sont utilisés afin de stimuler la fonction neuronale dans les maladies neurodégénératives et afin de traiter les maladies néoplasiques.