deoxyelephantopin

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: deoxyelephantopin
• 英文别名: DET；[(3S,4R,8R,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.04,8]pentadeca-1(15),9-dien-3-yl] 2-methylprop-2-enoate
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: JMUOPRSXUVOHFE-GZZMZBIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  deoxyelephantopin 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 [(3S,7R,8R,12R)-10-methyl-6-methylidene-5,14-dioxo-4,13-dioxatricyclo[10.2.1.03,7]pentadeca-1(15),9-dien-8-yl] 2-methylprop-2-enoate
  参考文献：
  名称：

  [EN] NOVEL SESQUITERPENE DERIVATIVES AND THEIR USE IN INFLAMMATION AND CANCER TREATMENT
  [FR] NOUVEAUX DÉRIVÉS SESQUITERPÈNE ET LEUR UTILISATION DANS LE TRAITEMENT DE L'INFLAMMATION ET DU CANCER

  摘要：

  揭示了一类新的倍半萜衍生物，适用于治疗癌症和炎症性疾病。这些去氧象蒿素衍生物在抑制患者体内癌细胞的增殖、迁移、活动性、侵袭、生长和/或转移方面具有有效性，或者在治疗患者时，用于增强另一种抗癌药物对癌细胞的抗增殖效果，或者用于使谷胱甘肽合成抑制剂对三阴性乳腺癌细胞活性的抑制具有敏感性和/或增强抗癌效果，或者用于治疗和/或预防患者体内脂多糖刺激引起的炎症反应，或者用于上述所有目的。还公开了制备去氧象蒿素衍生物的方法。

  公开号：

  WO2015188169A1

文献信息

• Cytotoxic germacranolides of Elephantopus carolinianus and the structure and stereochemistry of isodeoxyelephantopin
  作者：Decheng Zhang、Mitsumasa Haruna、Andrew T. McPhail、Kuo-Hsiung Lee

  DOI：10.1016/0031-9422(86)80023-1

  日期：——

  Elephantopus carolinianus yielded two cytotoxic sesquiterpene lactones, deoxyelephantopin and isodeoxyelephantopin, as well as 11β,13-dihydrodeoxyelephantopin which is devoid of cytotoxicity. The structures and stereochemistries of isodeoxyelephantopin and 11β,13-dihydrodeoxyelephantopin were determined by spectroscopic analysis, chemical transformations and X-ray analysis.

  摘要 北卡罗来纳象牙属carolinianus 的整个部分产生了两种细胞毒性倍半萜内酯，脱氧象素和异脱氧象素，以及无细胞毒性的11β,13-二氢脱氧象素。通过光谱分析、化学转化和 X 射线分析确定了异脱氧象素和 11β,13-二氢脱氧象素的结构和立体化学。
• Sesquiterpene derivatives and their use in inflammation or cancer treatment
  申请人：Academia Sinica

  公开号：US10238631B2

  公开（公告）日：2019-03-26

  A new class of sesquiterpene derivative useful for treating cancerous and inflammatory diseases are disclosed. These deoxyelephantopin derivatives are effective in suppressing proliferation, migration, mobility, invasion, growth, and/or metastasis of cancer cells in a patient, or useful for enhancing an anti-proliferative effect of another anti-cancer drug on cancer cells when treating a patient, or for sensitizing and/or enhancing an anti-cancer effect of a gluthathione synthesis blocker on inhibition of triple negative breast cancer cell activity, or for treatment and/or prophylaxis of lipopolysaccharide-stimulated inflammatory response in a patient, or for all of the above. Also disclosed are methods of preparing the deoxyelephantopin derivatives.

  本研究公开了一类可用于治疗癌症和炎症性疾病的新型倍半萜衍生物。这些脱氧苦艾素衍生物可有效抑制患者体内癌细胞的增殖、迁移、移动、侵袭、生长和/或转移，或在治疗患者时增强另一种抗癌药物对癌细胞的抗增殖作用、或用于增敏和/或增强谷胱甘肽合成阻滞剂对抑制三阴性乳腺癌细胞活性的抗癌作用，或用于治疗和/或预防患者体内脂多糖刺激的炎症反应，或用于上述所有用途。还公开了制备脱氧苦参碱衍生物的方法。
• TWI535725
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL SESQUITERPENE DERIVATIVES AND THEIR USE IN INFLAMMATION OR CANCER TREATMENT
  申请人：Academia Sinica

  公开号：US20170182001A1

  公开（公告）日：2017-06-29

  A new class of sesquiterpene derivative useful for treating cancerous and inflammatory diseases are disclosed. These deoxyelephantopin derivatives are effective in suppressing proliferation, migration, mobility, invasion, growth, and/or metastasis of cancer cells in a patient, or useful for enhancing an anti-proliferative effect of another anti-cancer drug on cancer cells when treating a patient, or for sensitizing and/or enhancing an anti-cancer effect of a gluthathione synthesis blocker on inhibition of triple negative breast cancer cell activity, or for treatment and/or prophylaxis of lipopolysaccharide-stimulated inflammatory response in a patient, or for all of the above. Also disclosed are methods of preparing the deoxyelephantopin derivatives.