N-(3a-(4-bromophenyl)-3-(3-fluorophenyl)-8b-hydroxy-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-yl)formamide | 1375796-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-(3a-(4-bromophenyl)-3-(3-fluorophenyl)-8b-hydroxy-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-yl)formamide
• 英文别名: N-[(1S,3S,3aR,8bS)-3a-(4-bromophenyl)-3-(3-fluorophenyl)-8b-hydroxy-6,8-dimethoxy-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-yl]formamide
• CAS: 1375796-51-2
• 化学式: C₂₆H₂₃BrFNO₅
• 分子量: 528.375
• InChiKey: LKNUGCKHKNWAFN-JWWGNVLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-fluorocinnamaldehyde 在 吡啶 、 硼烷四氢呋喃络合物 、 苄基三甲基氢氧化铵 、 溶剂黄146 、 zinc(II) iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 、 叔丁醇 为溶剂， 反应 33.5h， 生成 N-(3a-(4-bromophenyl)-3-(3-fluorophenyl)-8b-hydroxy-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-yl)formamide
  参考文献：
  名称：

  Flavaglines as Potent Anticancer and Cytoprotective Agents

  摘要：

  Flavaglines represent a family of plant natural products that display potent anticancer, Cardioprotective, and neuroprotective activities. Novel flavagline derivatives were synthesized and examined for their cytotoxicity on a panel of human cancer cell lines, their cardioprotection against doxorubicin-induced apoptosis in cardiomyocytes, and their neuroprotection in culture models of Parkinson's disease and cisplatin-induced neurotoxicity. The structural requirements of flavaglines for cardio and neuroprotection were for the first time unraveled and appeared to be slightly different from those for cytotoxicity on cancer cells. We provide also the first evidence that flavaglines may alleviate cisplatin-induced neurotoxicity, suggesting a prophylactic potential of these compounds to prevent this frequently encountered adverse effect of cancer chemotherapies.

  DOI：

  10.1021/jm301201z

文献信息

• [EN] FLAVAGLINE DERIVATIVES AS NEUROPROTECTIVE AGENTS<br/>[FR] DÉRIVÉS DE FLAVAGLINE EN TANT QU'AGENTS NEUROPROTECTEURS
  申请人：UNIV STRASBOURG

  公开号：WO2012066002A1

  公开（公告）日：2012-05-24

  The present invention discloses new flavagline derivatives (I) and the use of these compounds as neuroprotective and/or cardioprotective and/or antitumoral agents. In particular, the present invention discloses the use of these flavagline derivatives to prevent or limit the neurotoxicity of an antineoplastic agent. The use of these new compounds to prevent or treat a neurodegenerative disease of the nervous system, in particular Parkinson's disease, is also disclosed.

  本发明揭示了新的香豆素衍生物（I）及其作为神经保护和/或心脏保护和/或抗肿瘤药物的用途。具体来说，本发明揭示了利用这些香豆素衍生物预防或限制抗肿瘤药物的神经毒性的用途。还披露了利用这些新化合物预防或治疗神经系统的神经退行性疾病，特别是帕金森病。
• Flavagline derivatives as neuroprotective agents
  申请人：Université de Strasbourg

  公开号：EP2457907A1

  公开（公告）日：2012-05-30

  The present invention discloses new flavagline derivatives (I) and the use of these compounds as neuroprotective and/or cardioprotective and/or antitumoral agents. In particular, the present invention discloses the use of these flavagline derivatives to prevent or limit the neurotoxicity of an antineoplastic agent. The use of these new compounds to prevent or treat a neurodegenerative disease of the nervous system, in particular Parkinson's disease, is also disclosed.

  本发明公开了新的呋喃甘氨酸衍生物（I）以及将这些化合物用作神经保护和/或心脏保护和/或抗肿瘤剂的用途。具体而言，本发明公开了利用这些呋喃甘氨酸衍生物预防或限制抗肿瘤剂的神经毒性的用途。还公开了利用这些新化合物预防或治疗神经系统的神经退行性疾病，特别是帕金森病的用途。
• Flavaglines as Potent Anticancer and Cytoprotective Agents
  作者：Nigel Ribeiro、Frédéric Thuaud、Yohann Bernard、Christian Gaiddon、Thierry Cresteil、Audrey Hild、Etienne C. Hirsch、Patrick Pierre Michel、Canan G. Nebigil、Laurent Désaubry

  DOI：10.1021/jm301201z

  日期：2012.11.26

  Flavaglines represent a family of plant natural products that display potent anticancer, Cardioprotective, and neuroprotective activities. Novel flavagline derivatives were synthesized and examined for their cytotoxicity on a panel of human cancer cell lines, their cardioprotection against doxorubicin-induced apoptosis in cardiomyocytes, and their neuroprotection in culture models of Parkinson's disease and cisplatin-induced neurotoxicity. The structural requirements of flavaglines for cardio and neuroprotection were for the first time unraveled and appeared to be slightly different from those for cytotoxicity on cancer cells. We provide also the first evidence that flavaglines may alleviate cisplatin-induced neurotoxicity, suggesting a prophylactic potential of these compounds to prevent this frequently encountered adverse effect of cancer chemotherapies.