5,10-dimethoxy-2H-benzo[g]chromene | 1247716-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5,10-dimethoxy-2H-benzo[g]chromene
• CAS: 1247716-42-2
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: UITLWIBODDOOHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,10-dimethoxy-2H-benzo[g]chromene 在 ammonium cerium (IV) nitrate 、 palladium diacetate 、 silver carbonate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 8.25h， 生成
  参考文献：
  名称：

  Pterocarpanquinones, aza-pterocarpanquinone and derivatives: Synthesis, antineoplasic activity on human malignant cell lines and antileishmanial activity on Leishmania amazonensis

  摘要：

  Pterocarpanquinones (1a-e) and the aza-pterocarpanquinone (2) were synthesized through palladium catalyzed oxyarylation and azaarylation of conjugate olefins, and showed antineoplasic effect on leukemic cell lines (K562 and HL-60) as well as colon cancer (HCT-8), gliobastoma (SF-295) and melanoma (MDA-MB435) cell lines. Some derivatives were prepared (3-8) and evaluated, allowing establishing the structural requirements for the antineoplasic activity in each series. Compound 1a showed the best selectivity index in special for leukemic cells while 2 showed to be more bioselective for HCT-8, SF-295 and MDA-MB435 cells. Pterocarpanquinones 1a and 1c-e, as well as 8 were the most active on amastigote form of Leishmania amazonensis in culture. Compounds 1a, 1c and 8 showed the best selectivity index. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.025
• 作为产物：
  描述：

  、 硫酸二甲酯 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 5,10-dimethoxy-2H-benzo[g]chromene
  参考文献：
  名称：

  Pterocarpanquinones, aza-pterocarpanquinone and derivatives: Synthesis, antineoplasic activity on human malignant cell lines and antileishmanial activity on Leishmania amazonensis

  摘要：

  Pterocarpanquinones (1a-e) and the aza-pterocarpanquinone (2) were synthesized through palladium catalyzed oxyarylation and azaarylation of conjugate olefins, and showed antineoplasic effect on leukemic cell lines (K562 and HL-60) as well as colon cancer (HCT-8), gliobastoma (SF-295) and melanoma (MDA-MB435) cell lines. Some derivatives were prepared (3-8) and evaluated, allowing establishing the structural requirements for the antineoplasic activity in each series. Compound 1a showed the best selectivity index in special for leukemic cells while 2 showed to be more bioselective for HCT-8, SF-295 and MDA-MB435 cells. Pterocarpanquinones 1a and 1c-e, as well as 8 were the most active on amastigote form of Leishmania amazonensis in culture. Compounds 1a, 1c and 8 showed the best selectivity index. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.025

文献信息

• COMPOUNDS OF THE PTEROCARPANQUINONE FAMILY, METHOD FOR PREPARING THE SAME, PHARMACEUTICAL COMPOSITION CONTAINING THE NEW COMPOUNDS OF THE PTEROCARPANQUINONE FAMILY, USES AND THERAPEUTIC METHOD
  申请人：Da Silva Alcides Jose Monteiro

  公开号：US20110224289A1

  公开（公告）日：2011-09-15

  This invention belongs to the chemical-pharmaceutical field. New compounds of pterocarpanquinone family presented in formula (I) according to this invention are capable to be activated by reduction generating alkylating species intracellularly. It presents selective cytotoxic effects particularly on mammalian human and nonhuman cells that divide constantly and are useful in treating diseases and dysfunctions related to the phenomenon of undesired cell proliferation. Such compounds are also effective for the treatment of diseases or dysfunctions related to high levels of TNF-α in human and nonhuman mammals.

  这项发明属于化学制药领域。根据这项发明，公开的Pterocarpanquinone家族的新化合物在公式（I）中呈现，能够通过还原激活产生细胞内烷基化物种。它对哺乳动物人类和非人类细胞表现出选择性细胞毒作用，特别对那些不断分裂的细胞，对治疗与不受欢迎的细胞增殖现象相关的疾病和功能障碍有用。这些化合物也对治疗人类和非人类哺乳动物体内TNF-α水平过高相关的疾病或功能障碍有效。
• Palladium-catalyzed oxyarylation of olefins using silver carbonate as the base. Probing the mechanism by electrospray ionization mass spectrometry
  作者：Camilla D. Buarque、Vagner D. Pinho、Boniek Gontijo Vaz、Marcos N. Eberlin、Alcides J.M. da Silva、Paulo R.R. Costa

  DOI：10.1016/j.jorganchem.2010.05.014

  日期：2010.8

  (8 and 12) and electron-poor (10) olefins by ortho-iodophenols (3a–d) was studied using Ag2CO3 as the base, in acetone, and in the presence and absence of PPh3. The corresponding adducts of oxyarylation were obtained in moderate yields. The reaction mechanism was examined by electrospray ionization mass spectrometry (ESI-MS). Cationic arylpalladium intermediate (14), formed by the oxidative insertion

  以Ag 2 CO 3为碱，在丙酮中研究了邻碘苯酚（3a - d）的Pd（OAc）2催化富电子（8和12）和贫电子（10）烯烃的氧化芳基化。在有和没有PPh的情况下3。以中等收率获得了相应的氧化芳基加合物。通过电喷雾电离质谱法（ESI-MS）检查反应机理。通过将Pd（0）氧化插入3a形成的阳离子芳基钯中间体（14）和阳离子Palladacycles（15通过14与烯烃8和12的反应获得的）被ESI-MS截获并通过ESI-MS / MS进行表征。