5-hydroxy-3,7-dimethoxy-1,4-phenanthraquinone, denbinobin | 82526-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5-hydroxy-3,7-dimethoxy-1,4-phenanthraquinone, denbinobin
• 英文别名: 5-hydroxy-3,7-dimethoxy-1,4-phenanthrenequinone；5-hydroxy-3,7-dimethoxy-1,4-phenanthraquinone；5-hydroxy-3,7-dimethoxy-1,4-phenanthrenedione；Denbinobin；5-hydroxy-3,7-dimethoxyphenanthrene-1,4-dione
• CAS: 82526-36-1
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: KYOONHCJRPIMJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3,7-dimethoxy-1,4-phenanthraquinone, denbinobin 在 potassium nitrososulfonate 、 sodium acetate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以91%的产率得到2,6-dimethoxy-1,4,5,8-phenanthrenetetrone
  参考文献：
  名称：

  Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

  摘要：

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.054
• 作为产物：
  描述：

  2-溴-3-羟基-4-甲氧基苯甲醛 在 正丁基锂 、 potassium nitrososulfonate 、 偶氮二异丁腈 、 碘代三甲硅烷 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium acetate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 5-hydroxy-3,7-dimethoxy-1,4-phenanthraquinone, denbinobin
  参考文献：
  名称：

  简洁的树皮素合成

  摘要：

  通过分子内自由基环化和弗雷米氏盐介导的氧化反应作为关键反应，描述了树皮素的简明合成。从可商购获得的3,5-二甲氧基苄基溴（6）和2-溴异香草醛（5）开始的七步过程有效地构建了天然产物树皮菌素（1）。

  DOI：

  10.1016/j.tetlet.2005.09.118

文献信息

• Total Synthesis of Denbinobin
  作者：Hsueh-Yun Lee、Sunil Kumar、Tzu-Cheng Lin、Jing-Ping Liou

  DOI：10.1021/acs.jnatprod.5b00959

  日期：2016.4.22

  A total synthesis of denbinobin (1) in seven steps with an overall yield of 10% is reported. This synthesis used an FeCl3-assisted cyclization of stilbene to form a phenanthrene. The poor yields of the decarboxylation and methoxylation steps were improved upon to become essentially quantitative. This scalable methodology was carried out using ordinary laboratory reagents.

  据报道，七个步骤的全合成树皮素（1）的总产率为10％。该合成使用FeCl 3辅助的苯乙烯环化形成菲。脱羧和甲氧基化步骤的产率很低，基本上就定量了。这种可扩展的方法是使用普通实验室试剂进行的。
• <i>In Vitro</i>and<i>In Vivo</i>Antitumoral Phenanthrenes from the Aerial Parts of<i>Dendrobium nobile</i>
  作者：You Lee、Jong Park、Nam Beak、Shin Kim、Byung Ahn

  DOI：10.1055/s-2006-958043

  日期：1995.4

  Two phenanthrenes were isolated from the aerial part of Dendrobium nobile Lindl. and their structures were identified to be 4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene (1) and denbinobin (2), among which the former has been first isolated from this plant. These two compounds were found to be cytotoxic against A549 (human lung carcinoma), SK-OV-3 (human ovary adenocarcinoma), and HL-60 (human promyelocytic leukemia) cell lines. Compound 1 also showed antitumor activity on the life span of ICR mice intraperitoneally implanted with 1 × 106 cells of sarcoma 180.

  从金钗石斛（Dendrobium nobile Lindl.）的气生部分分离出两种菲，并确定其结构为 4,7-二羟基-2-甲氧基-9,10-二氢菲（1）和脱氢菲（2），其中前者是首次从该植物中分离出来。研究发现，这两种化合物对 A549（人类肺癌）、SK-OV-3（人类卵巢腺癌）和 HL-60（人类早幼粒细胞白血病）细胞株具有细胞毒性。化合物 1 还对腹腔植入 1 × 106 个肉瘤 180 细胞的 ICR 小鼠的寿命具有抗肿瘤活性。
• A composition containing non-psychotropic cannabinoids for the treatment of inflammatory diseases
  申请人：Vivacell Biotechnology Espana S.L.

  公开号：EP2044935A1

  公开（公告）日：2009-04-08

  A composition containing non-psychotropic cannabinoids for the treatment of inflammatory diseases. The invention relates to a composition comprising at least one non-psycotropic cannabinoid and/or at least one phenolic or flavonoid compound and/or Denbinobin and their uses for the prevention and treatment of gastrointestinal inflammatory diseases and for the prevention and treatment of gastrointestinal cancers. It also relates to a phytoextract obtained from the plant Cannabis sativa, more particularly from the selected variety CARMA.

  一种含有非精神类大麻素的组合物，用于治疗炎症性疾病。 本发明涉及一种含有至少一种非精神类大麻素和/或至少一种酚类或黄酮类化合物和/或 Denbinobin 的组合物及其用于预防和治疗胃肠道炎症疾病和预防和治疗胃肠道癌症的用途。它还涉及一种从大麻（Cannabis sativa）植物，特别是从所选品种 CARMA 中提取的植物提取物。
• Obesity small molecules
  申请人：Akron Molecules GmbH

  公开号：EP2633884A1

  公开（公告）日：2013-09-04

  The present invention relates to new therapies to treat obesity and related diseases, as well as for reducing triglyceride levels and body weight.

  本发明涉及治疗肥胖症和相关疾病以及降低甘油三酯水平和体重的新疗法。
• FMO3 inhibitors for treating pain
  申请人：Akron Molecules GmbH

  公开号：EP2674161A1

  公开（公告）日：2013-12-18

  The present invention relates to new therapies to treat pain and related diseases, as well as pharmaceutical compounds for use in said therapies.

  本发明涉及治疗疼痛和相关疾病的新疗法，以及用于上述疗法的药物化合物。