(Z)-6,7-epoxyligustilide | 106533-40-8

• 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)-6,7-epoxyligustilide
• 英文别名: Z-6,7-Epoxyligustilide；(4Z)-4-butylidene-1a,2,3,6b-tetrahydrooxireno[2,3-g][2]benzofuran-6-one
• CAS: 106533-40-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: ZCTBULGQERTBEG-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯酞 在 吡啶 、 氨 、 sodium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 丙酮 为溶剂， 反应 72.0h， 生成 3,8-epoxyligustilide 、 (Z)-6,7-epoxyligustilide
  参考文献：
  名称：

  直接和金属催化的 Phthalide (Z)-Ligustilide 的光化学二聚导致 [2 + 2] 和 [4 + 2] Cyclloadducts：在 Tokinoides AC 和 Riligustilide 的全合成中的应用。

  摘要：

  合成衍生的 ( Z )-川芎内酯 ( 1 ) 在一系列条件下进行了光化学促进的二聚化过程。通过这种方式，改变二聚的天然产物tokinolides A-C（的分布4，3，和6，分别地）和riligustilide（5如已经获得很好某些相关的（异构体）的化合物）。其中三个的结构已通过单晶 X 射线分析得到证实。讨论了本研究结果的生物合成影响。

  DOI：

  10.1021/acs.orglett.9b02172

文献信息

• Use of Phthalide Derivatives
  申请人：Chen Fei

  公开号：US20080255061A1

  公开（公告）日：2008-10-16

  Disclosed a class of phthalide derivatives and the use of which to manufacture the sensitizer or reverser of the antineoplastic agent. The phthalide derivatives according to the invention can enhance the sensitivity of drug-resistance tumor cells against chemotherapy and decrease the drug-resistance of tumor cells 5-30 folder and enhance notably several chemotherapy agents-induced apoptosis of tumor cells
• Method For Improving The Oxygen-Releasing Ability Of Hemoglobin To Organs Or Peripheral Tissues In Human Bodies And A Medication Thereof
  申请人：NATIONAL SUN YAT-SEN UNIVERSITY

  公开号：US20170129866A1

  公开（公告）日：2017-05-11

  A method for improving the oxygen-releasing ability of hemoglobin, hemoglobin variants, recombinant hemoglobin or hemoglobin-based blood substitutes to organs or peripheral tissues in human bodies is disclosed by administering a compound of phthalides to a subject in need thereof. The compound of phthalides is characterized by a phthalide functional group which is represented as Formula I, and forms at least one hydrogen bond with αArg141 of hemoglobin, hemoglobin variants, recombinant hemoglobin or hemoglobin-based blood substitutes, stabilizing the α1/α2 interface of hemoglobin, further stabilizing the oxygenated hemoglobin, hemoglobin variants, recombinant hemoglobin or hemoglobin-based blood substitutes in the low oxygen affinity “T” state and facilitating the oxygen release to the organs or the peripheral tissues. A medication for improving the oxygen-releasing ability of hemoglobin, hemoglobin variants, recombinant hemoglobin, or hemoglobin-based blood substitutes to organs or peripheral tissues in human bodies is also disclosed.
• METHOD FOR ENHANCING THE OXYGENATION LEVEL OF TISSUE CELLS AS AN ALTERNATIVE METHOD FOR HYPERBARIC OXYGEN THERAPY
  申请人：National Sun Yat-sen University

  公开号：US20170266155A1

  公开（公告）日：2017-09-21

  The present invention relates to a method for substituting for or acting with the hyperbaric oxygen therapy to improve hypoxia, comprising the step of: administrating a phthalide compound to a subject in need thereof, wherein the phthalide compound can increase the oxygen release efficiency of blood hemoglobin (Hb) in the subject and further increase the cellular oxygenation level, and when the phthalide compound substitutes for or act with the hyperbaric oxygen therapy, the common adverse side effects of the hyperbaric oxygen therapy, such as barotrauma, decompression sickness and oxygen poisoning, are prevented. The phthalide compound is used to substitute for or act with 2,3 -BPG, to modulate and decrease the oxygen affinity of hemoglobin (Hb), to increase the oxygen release efficiency of hemoglobin (Hb) to tissue cells, thereby achieving a normal cellular oxygenation level and maintaining the cellular oxygenation level in a normal range.
• METHOD FOR PREVENTING CANCER BY USING PHTHALIDES
  申请人：National Sun Yat-sen University

  公开号：US20170266156A1

  公开（公告）日：2017-09-21

  The present invention relates to a method for preventing cancer by using a phthalide compound, wherein the phthalide compound has an effect of increasing the oxygen release efficiency of hemoglobin (Hb) of a subject to increase the oxygenation level of organs and tissue cells, thereby preventing the cellular oxygenation level against falling below the critical cellular oxygen requirements under which the normal cells can turn cancerous. Although cancer may be caused by a variety of reasons, including congenital inheritance, external environment, air pollution or poor living and dietary habits, there is only one primary and common reason in causing cancers, the excessively low cellular oxygenation level. When the oxygenation level of any cell falls below 60% of its physiological oxygen requirements, the normal cell may turn cancerous. The present invention is to use the phthalide compound to substitute for or cooperate with 2,3-BPG of a subject to lower the oxygen affinity of hemoglobin (Hb) and to facilitate the release of oxygen from hemoglobin to tissue cells, as a result, the cellular oxygenation level is maintained always higher than the critical threshold for the normal cells to turn cancerous, and by doing so to prevent the normal cells from turning cancerous and prevent the developments of cancers.
• METHOD FOR TREATING ALZHEIMER'S DISEASE AND 2, 3-BIPHOSPHOGLYCERATE METABOLISM DISORDER INDUCED
  申请人：National Sun Yat-sen University

  公开号：US20170266154A1

  公开（公告）日：2017-09-21

  The present invention relates to a method for treating Alzheimer's disease and 2,3-BPG metabolic disorder induced morbidities, comprising administrating a phthalide compound to an Alzheimer's disease patient or a patient having 2,3-BPG metabolic disorder induced morbidities, wherein the method is characterized by that the phthalide compound has the same effect as 2,3-BPG on modulating hemoglobin to reduce its oxygen affinity and can thus act as a 2,3-BPG functional substitute when the 2,3-BPG concentration is too low in the Alzheimer's disease patient or in the patient having 2,3-BPG metabolic disorder induced morbidities to maintain the normal oxygen release function of hemoglobin and therefore to maintain the normal cellular oxygenation level.