(1R)-6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol | 87004-99-7

• 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: (1R)-6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol
• 英文别名: panaxytriol-9,10-acetonide；(3R,9R,10R)-panaxytriol acetonide；(3R)-8-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]oct-1-en-4,6-diyn-3-ol
• CAS: 87004-99-7
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: JVJTWOPEMAGFNK-GUDVDZBRSA-N

物化性质

• 沸点：
  436.0±45.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol 在 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (E)-8-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]oct-2-en-4,6-diyn-1-ol
  参考文献：
  名称：

  JP5822991

  摘要：

  公开号：
• 作为产物：
  描述：

  (2R,3R)-1,2-epoxy-3-decanol 在 吡啶 、 四甲基乙二胺 、 氧气 、 sodium methylate 、 对甲苯磺酸 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 丙酮 为溶剂， 反应 14.5h， 生成 (1R)-6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol
  参考文献：
  名称：

  Synthesis of a new type of antitumour agent panaxytriol: Synthesis of its four diastereomers

  摘要：

  Synthesis of four diastereomers of panaxytriol has been described. The basic objective is to create two acetylenic precursors followed by cuprous chloride mediated C-C bond coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00732-2

文献信息

• The Absolute Stereostructure of Panaxytriol,a Biologically Active Diacetylenic Acetogenin, from Ginseng Radix Rubra.
  作者：Motomasa KOBAYASHI、Taifo MAHMUD、Takashi UMEZOME、Isao KITAGAWA

  DOI：10.1248/cpb.43.1595

  日期：——

  The absolute stereostructure of panaxytriol (1), a diacetylenic constituent of Ginseng Radix Rubra, was determined by applying the modified Mosher method and the CD exciton chirality method to be expressed as (3R, 9R, 10R)-heptadec-1-ene-4, 6-diyne-3, 9, 10-triol.

  通过改良莫舍尔法和 CD 激发子手性法，确定了人参中的一种二乙酰基成分--三七三醇（1）的绝对立体结构，并将其表示为（3R, 9R, 10R）-十七-1-烯-4, 6-二炔-3, 9, 10-三醇。
• COMPOUNDS, COMPOSITIONS AND METHODS FOR REDUCING TOXICITY AND TREATING OR PREVENTING DISEASES
  申请人：Danishefsky Samuel J.

  公开号：US20110312904A1

  公开（公告）日：2011-12-22

  The present invention provides compounds of Formula (I), compositions comprising an effective amount of a compound of Formula (I), optionally with chemotherapeutic drugs such as a tubulin-binding drug, and methods of their use for reducing the toxicity of cytotoxic agents, treating or preventing cancer or a neuropathic disorder, inducing a chemoprotective phase II enzyme, DNA, or protein synthesis, enhancing the immune system, treating inflammation, improving and enhancing general health or well-being, and methods for making compounds of Formula (I).

  本发明提供了公式(I)的化合物，以及包含公式(I)化合物的有效量的组合物，可选地与化疗药物如微管结合药物一起使用，并用于减少细胞毒性药物的毒性，治疗或预防癌症或神经病理性障碍，诱导化学保护性II期酶、DNA或蛋白质合成，增强免疫系统，治疗炎症，改善和增强整体健康或福祉，以及制备公式(I)化合物的方法。
• COMPOSITIONS AND METHODS FOR TREATING CANCER OR A NEUROTROPHIC DISORDER
  申请人：Danishefsky Samuel J.

  公开号：US20110124690A1

  公开（公告）日：2011-05-26

  The present invention relates to compositions comprising an effective amount of a Panaxytriol Compound and a tubulin-binding drug, methods for treating or preventing cancer or a neurotrophic disorder comprising administering to a subject in need thereof an effective amount of a Panaxytriol Compound and a tubulin-binding drug, and methods for making a Panaxytriol Compound.

  本发明涉及组合物，包括有效量的泛沙三醇化合物和微管结合药物，治疗或预防癌症或神经营养障碍的方法包括向需要的受体中投与有效量的泛沙三醇化合物和微管结合药物，以及制备泛沙三醇化合物的方法。
• Total Synthesis of (3<i>R</i>,9<i>R</i>,10<i>R</i>)-Panaxytriol via Tandem Metathesis and Metallotropic [1,3]-Shift as a Key Step
  作者：Eun Jin Cho、Daesung Lee

  DOI：10.1021/ol702651s

  日期：2008.1.1

  Enyne metathesis is unique for its capacity to carry out multiple bond formation in tandem fashion. Its combined use with metallotropic [1,3]-shift allowed for the development of a novel strategy for the total synthesis of a conjugated 1,3-diyne-containing natural product (3R,9R,10R)-panaxytriol.
• Total Synthesis as a Resource in Drug Discovery:  The First In Vivo Evaluation of Panaxytriol and Its Derivatives
  作者：Heedong Yun、Ting-Chao Chou、Huajin Dong、Yuan Tian、Yue-ming Li、Samuel J. Danishefsky

  DOI：10.1021/jo0515475

  日期：2005.12.1

  We have conducted key preliminary studies into the in vitro and in vivo cytotoxicity of panaxytriol. Through total synthesis, we prepared and evaluated several synthetic panaxytriol analogues, each of which exhibited enhanced cytotoxicity relative to the natural product. Consequently, we have begun to chart the first in vitro SAR map for the compound, which suggests that the C-3 hydroxyl functionality is not critical for biological activity and that, in fact, engagement of the C-9-C-10 diol as an acetonide actually leads to notably enhanced cytotoxicity. Furthermore, through in vivo investigations, we demonstrated that panaxytriol and panaxytriol acetonide (12) moderately suppress tumor growth with little or no toxicity. Finally, preliminary in vitro evaluation of panaxytriol indicates that it possesses neurotrophic activity.