3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-yl acetate | 1228174-35-3

• 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: 3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-yl acetate
• 英文别名: [(1R,3S,3aR,8bS)-3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-yl] acetate
• CAS: 1228174-35-3
• 化学式: C₂₇H₂₅BrO₆
• 分子量: 525.396
• InChiKey: YQERSSSARDFXSG-MPYVGDORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3S,3aR,8bR)-3a-(4-bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydrocyclopenta[b][1]benzofuran-1-one 在 吡啶 、 4-二甲氨基吡啶 、 tetramethylammonium triacetoxyborohydride 作用下， 以 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 acetate
  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

文献信息

• 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。
• [EN] ROCAGLAOL DERIVATIVES AS CARDIOPROTECTANT AGENTS AND AS ANTINEOPLASTIC AGENTS<br/>[FR] DÉRIVÉS DU ROCAGLAOL EN TANT QU'AGENTS CARDIOPROTECTEURS ET AGENTS ANTINÉOPLASIQUES
  申请人：UNIV STRASBOURG

  公开号：WO2010060891A1

  公开（公告）日：2010-06-03

  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.
• 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