洋川芎内酯I | 94596-28-8

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 中文名称: 洋川芎内酯I
• 英文名称: senkyunolide I
• 英文别名: (3Z,6S,7S)-3-butylidene-6,7-dihydroxy-4,5,6,7-tetrahydro-2-benzofuran-1-one
• CAS: 94596-28-8
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: DQNGMIQSXNGHOA-JXQVETIVSA-N

物化性质

• 沸点：
  444.8±45.0 °C(Predicted)
• 密度：
  1.28
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

概述

洋川芎内酯I（SEnkyunolide I, SENI）是从川芎及当归等中药中提取的一种苯酞类化合物。它具有良好的脂溶性和水溶性，能够迅速进入血液和脑脊液，展现出一定的新药开发潜力。其主要的药理作用包括：减轻ConA诱导的红细胞变形性损伤与聚集；抑制豚鼠心肌细胞及人神经细胞瘤的钙内流；降低缺血再灌注动物模型中脑干内的NO水平，并抑制NO合酶的活性。

生物活性

SEnkyunolide I（SEI, SENI）是一种从Ligusticum chuanxiong 中提取的口服活性化合物，具有止痛、抗偏头痛、神经保护、抗氧化和抗凋亡等生物活性。它可上调Erk1/2 的磷酸化，并诱导Nrf2的核易位，伴随HO-1和NQO1的表达增强。此外，SEI 还能够提高 Bcl-2/Bax 比例，并抑制裂化的caspaSE 3 和 caspaSE 9 表达。

靶点

Target	Value
Erk1
Erk2
Nrf2
Bcl-2/Bax
CaspaSE-3

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化学性质

洋川芎内酯I为微黄色油状物，可溶于甲醇、乙醇和DMSO等有机溶剂。该化合物来源于川芎根茎。

用途

洋川芎内酯I具有脑保护作用，主要用于含量测定/鉴定/药理实验等。此外，它还用于治疗妇科疾病、缓解肌肉紧张，并具有抗惊厥作用。对小鼠主动脉平滑肌培养细胞有抗增殖作用，但其效果弱于洋川穹内酯H和J。

文献信息

• USE OF PHTHALIDE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF DIABETES MELLITUS
  申请人：DSM IP Assets B.V.

  公开号：EP1622605B1

  公开（公告）日：2009-07-15
• Use of phthalide derivatives for the treatment and prevention of diabetes mellitus
  申请人：D'Orazio Daniel

  公开号：US20070082947A1

  公开（公告）日：2007-04-12

  The present invention relates to the use of a compound as effective agent for the prevention or treatment of diabetes mellitus in a mammal. Said compounds being selected from the group of phthalide derivatives and exhibit excellent blood glucose lowering effects and thus are effective agents in the prevention or treatment of diabetes mellitus in mammals.
• NOVEL USE OF ORGANIC COMPOUNDS
  申请人：Fowler Ann

  公开号：US20090176873A1

  公开（公告）日：2009-07-09

  The present invention relates to the use of compounds of the formula (I) wherein the clotted line is an optional bond; R 1 is butyl or butyryl if R 2 is hydroxyl but is butyl if R 2 is hydrogen; or R 1 and R 2 taken together are 1-butylidene optionally substituted by hydroxyl, methyl, or 3-(α,β-dimethylacrylyloxy)-pentylidenyl; X is a residue selected from the group consisting of X1, X2, X3, X4, and X5; wherein X is X2, X3 or X5 if the dotted line in formula (I) is absent; and X is X1, X4 or X5 if the dotted line signifies a bond in formula (I) above; R 3 is hydroxyl or butyryl; and n is 1 or 2, as agents for the prevention, control and treatment of conditions requiring modulation of inflammation in mammals. In another aspect, the present invention relates to the use of compounds of the formula (I) as active ingredients in the manufacture of medicaments/compositions for the prevention, control and treatment of conditions requiring modulation of inflammation. The compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the management of pain, fever and injuries, especially sport injuries. Moreover, the compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the maintenance and regeneration of articular cartilage.
• ORGANIC COMPOUNDS FOR TREATMENT OF DISORDERS CONNECTED TO IMPAIRED NEUROTRANSMISSION
  申请人：De Saizieu Antoine

  公开号：US20100184852A1

  公开（公告）日：2010-07-22

  The present invention refers to compounds of the general formula (I) wherein R 1 is hydrogen or hydroxy; R 2 is butyl or butyryl if R 1 is hydroxy, but R 2 is butyl if R 1 is hydrogen; or R 3 and R 2 taken together are 1-propylidene or 1-butylidene optionally substituted by hydroxy, methyl, or 3-(α, β-dimethylacryloyloxy); the dotted line is an optional bond; X is an optionally substituted aliphatic C4-residue selected from the group consisting of X1, X2, X3, X4, and X5; wherein X is X2, X3 or X5 if the dotted line in formula (I) is absent; and X is X1, X4 or X5 if the dotted line signifies a bond in formula (I) above; R 3 and R 4 are, independently from each other, hydrogen or hydroxy; and R 5 is hydroxy or butyryl, for use in the treatment of disorders connected to impaired neurotransmission, as well as to dietary and pharmaceutical compositions containing such compounds, and their uses.
• Anti-inflammatory compositions and their use
  申请人：Fowler Ann

  公开号：US20100298427A1

  公开（公告）日：2010-11-25

  The present invention relates to the use of compounds of the formula (I) wherein the clotted line is an optional bond; R 1 is butyl or butyryl if R 2 is hydroxyl but is butyl if R 2 is hydrogen; or R 1 and R 2 taken together are 1-butylidene optionally substituted by hydroxyl, methyl, or 3-(α,β-dimethylacrylyloxy)-pentylidenyl; X is a residue selected from the group consisting of X1, X2, X3, X4, and X5; wherein X is X2, X3 or X5 if the dotted line in formula (I) is absent; and X is X1, X4 or X5 if the dotted line signifies a bond in formula (I) above; R 3 is hydroxyl or butyryl; and n is 1 or 2, as agents for the prevention, control and treatment of conditions requiring modulation of inflammation in mammals. In another aspect, the present invention relates to the use of compounds of the formula (I) as active ingredients in the manufacture of medicaments/compositions for the prevention, control and treatment of conditions requiring modulation of inflammation. The compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the management of pain, fever and injuries, especially sport injuries. Moreover, the compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the maintenance and regeneration of articular cartilage.