2-(4-bromophenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one | 1186012-87-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-bromophenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one
• 英文别名: 7-Methoxy-4'-bromoflavonol；2-(4-bromophenyl)-3-hydroxy-7-methoxychromen-4-one
• CAS: 1186012-87-2
• 化学式: C₁₆H₁₁BrO₄
• 分子量: 347.165
• InChiKey: ZRVUOUIUGJLGBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one 在 氨 、 sodium methylate 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 51.33h， 生成 (1R,2R,3S,3aR,8bS)-3a-(4-bromophenyl)-1,8b-dihydroxy-6-methoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
  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：

  (E)-3-(4-bromophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 在 potassium hydroxide 、 双氧水 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以70%的产率得到2-(4-bromophenyl)-3-hydroxy-7-methoxy-4H-chromen-4-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 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。
• Synthesis, inverse docking-assisted identification and in vitro biological characterization of Flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers
  作者：Tithi Roy、Samuel T. Boateng、Sergette Banang-Mbeumi、Pankaj K. Singh、Pratik Basnet、Roxane-Cherille N. Chamcheu、Federico Ladu、Isabel Chauvin、Vladimir S. Spiegelman、Ronald A. Hill、Konstantin G. Kousoulas、Bolni Marius Nagalo、Anthony L. Walker、Jean Fotie、Siva Murru、Mario Sechi、Jean Christopher Chamcheu

  DOI：10.1016/j.bioorg.2020.104595

  日期：2021.2
• Synthetic Analogue of Rocaglaol Displays a Potent and Selective Cytotoxicity in Cancer Cells: Involvement of Apoptosis Inducing Factor and Caspase-12
  作者：Frédéric Thuaud、Yohann Bernard、Gülen Türkeri、Ronan Dirr、Geneviève Aubert、Thierry Cresteil、Aurélie Baguet、Catherine Tomasetto、Yuri Svitkin、Nahum Sonenberg、Canan G. Nebigil、Laurent Désaubry

  DOI：10.1021/jm900365v

  日期：2009.8.27

  Flavaglines constitute a family of natural anticancer compounds. We present here 3 (FL3), the first synthetic flavagline that inhibits cell proliferation and viability (IC50 approximate to 1 nM) at lower doses than did the parent compound, racemic rocaglaol. Compound 3 enhanced doxorubicin cytotoxicity in HepG2 cells and retained its potency against. adriamycin-resistant cell lines without inducing cardiomyocyte toxicity. Compound 3 induced apoptosis of HL60 and Hela cells by triggering the translocation of Apoptosis Inducing Factor (AIF) and caspase-12 to the nucleus. A fluorescent conjugate of 3 accumulated ill endoplasmic reticulum (ER), suggesting that flavaglines bind to their target in the ER. where it triggers a cascade of events that leads to the translocation of AIF and caspase-12 to the nucleus and probably inhibition of eIF4A. Our studies highlight structural features critical to their antineoplastic potential and suggest that these compounds would retain their activity in cells refractory to caspase activation.
• [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.
• 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。