(3S,3aR,8bR)-3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydrocyclopenta[b][1]benzofuran-1-one | 1227475-68-4

• 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: (3S,3aR,8bR)-3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydrocyclopenta[b][1]benzofuran-1-one
• CAS: 1227475-68-4
• 化学式: C₂₅H₂₁BrO₅
• 分子量: 481.343
• InChiKey: AITHJNKCUXDEQP-OWAUWMPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,3aR,8bR)-3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydrocyclopenta[b][1]benzofuran-1-one 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta-[b]benzofuran-1-yl formate
  参考文献：
  名称：

  Novel Flavaglines Displaying Improved Cytotoxicity

  摘要：

  Novel flavagline analogues were synthesized and examined with respect to their cytotoxicity Structural features critical to the potential of this class of anticancer natural products wet e unraveled We demonstrated, in particular, that the introduction of substituants at C-2 has a deleterious effect on multidrug resistance Replacement of the hydroxy at C-1 by an aminoformyl with the opposite configuration enhances the cytotoxicity and led to a compound that reduces tumors growth in an allograft model at nontoxic doses

  DOI：

  10.1021/jm101318b
• 作为产物：
  描述：

  rac-(S)-3-((R)-2,3-dihydro-4,6-dimethoxy-2-(4-bromophenyl)-3-oxobenzofuran-2-yl)-3-phenyl-2-[(trimethylsilyl)oxy]-propanenitrile 在 lithium diisopropyl amide 、 水 、 氯化铵 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以20%的产率得到(3S,3aR,8bR)-3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydrocyclopenta[b][1]benzofuran-1-one
  参考文献：
  名称：

  Rocaglaol derivatives as cardioprotectant agents

  摘要：

  本发明公开了新的罗钙素衍生物及其用途，用于预防或限制抗肿瘤剂的心脏毒性，特别是用于预防或限制由该剂诱导的心肌细胞凋亡。

  公开号：

  EP2189453A1

文献信息

• Rocaglaol derivatives as cardioprotectant agents
  申请人：Université Louis Pasteur

  公开号：EP2189453A1

  公开（公告）日：2010-05-26

  The present invention discloses new rocaglaol derivatives and the use of rocaglaol derivatives to prevent or to limit the cardiotoxicity of an antineoplastic agent, in particular to prevent or to limit the apoptosis of cardiomyocytes induced by such agent.

  本发明公开了新的罗钙素衍生物及其用途，用于预防或限制抗肿瘤剂的心脏毒性，特别是用于预防或限制由该剂诱导的心肌细胞凋亡。
• [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。
• ROCAGLAOL DERIVATIVES AS CARDIOPROTECTANT AGENTS AND AS ANTINEOPLASTIC AGENTS
  申请人：Desaubry Laurent

  公开号：US20120101153A1

  公开（公告）日：2012-04-26

  The present invention discloses new rocaglaol derivatives and the use of rocaglaol derivatives to prevent or to limit the cardiotoxicity of an antineoplastic agent, in particular to prevent or to limit the apoptosis of cardiomyocytes induced by such agent.

  本发明揭示了新的洛卡格洛衍生物，并使用洛卡格洛衍生物来预防或限制抗肿瘤药物的心脏毒性，特别是预防或限制由该药物引起的心肌细胞凋亡。
• Novel Flavaglines Displaying Improved Cytotoxicity
  作者：Frédéric Thuaud、Nigel Ribeiro、Christian Gaiddon、Thierry Cresteil、Laurent Désaubry

  DOI：10.1021/jm101318b

  日期：2011.1.13

  Novel flavagline analogues were synthesized and examined with respect to their cytotoxicity Structural features critical to the potential of this class of anticancer natural products wet e unraveled We demonstrated, in particular, that the introduction of substituants at C-2 has a deleterious effect on multidrug resistance Replacement of the hydroxy at C-1 by an aminoformyl with the opposite configuration enhances the cytotoxicity and led to a compound that reduces tumors growth in an allograft model at nontoxic doses