9-Cinnamoylanthracene | 55805-52-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 9-Cinnamoylanthracene
• 英文别名: 9-anthryl styryl ketone；1-(Anthracen-9-yl)-3-phenylprop-2-en-1-one；(E)-1-anthracen-9-yl-3-phenylprop-2-en-1-one
• CAS: 55805-52-2
• 化学式: C₂₃H₁₆O
• 分子量: 308.379
• InChiKey: VRBVYRUYQIRTOW-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-Cinnamoylanthracene 、 3-diazo-1-ethylindolin-2-one 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 0.33h， 以53%的产率得到3-[2-(anthracen-9-yl)-2-oxoethyl]-1-ethyl-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  BF3·OEt2 催化 α,β-烯酮的化学选择性 CC 键断裂：3-烷基化羟吲哚和螺吲哚环氧乙烷的意外合成

  摘要：

  开发了一种BF 3 ·OEt 2催化的α,β-烯酮与重氮酰胺的高化学选择性形式C C双键裂解反应，用于合成3-烷基化羟吲哚类化合物。发现三氟化硼醚合物是化学选择性 C α -C β裂解烯酮以获得 3-烷基化羟吲哚的有效催化剂。产物的形成表明以廉价的BF 3 ·OEt 2为催化剂， α,β-烯酮的选择性β-碳消除途径，无过渡金属条件，露天环境，良好的功能耐受性和广泛的底物范围。该协议的合成效用通过合成螺吲哚环氧乙烷来突出。

  DOI：

  10.1039/d1ob02002a
• 作为产物：
  描述：

  蒽 、 肉桂酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以27%的产率得到9-Cinnamoylanthracene
  参考文献：
  名称：

  2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis

  摘要：

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.

  DOI：

  10.1021/jm00062a016

文献信息

• Synthesis and biological evaluation of aromatic enones related to curcumin
  作者：Thomas Philip Robinson、Richard B. Hubbard、Tedman J. Ehlers、Jack L. Arbiser、David J. Goldsmith、J. Phillip Bowen

  DOI：10.1016/j.bmc.2005.03.054

  日期：2005.6

  It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or

  姜黄素是从香料姜黄中分离得到的天然产物，已显示出广泛的药理活性，包括某些抗癌特性。它已被明确地证明是在体外和体内血管生成的有效抑制剂。使用姜黄素作为抗血管生成类似物设计的先导化合物，已经合成了一系列利用取代的查尔酮骨架的结构相关化合物，并通过已建立的SVR细胞增殖测定法进行了测试。结果产生了范围广泛的化合物，这些化合物等于或超过姜黄素体外抑制内皮细胞生长的能力。由于它们的商业可获得性和相当简单的合成制备方法，这些低分子量化合物是开发未来血管生成抑制剂的诱人线索。
• Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：——

  公开号：US20020040029A1

  公开（公告）日：2002-04-04

  The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The present invention also relates to the use of chalcone and its analogs as antitumor/anticancer agents and to treat a number of conditions or disease states in which angiogenesis is a factor, including angiongenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及香豆素和香豆素衍生物以及类似物，这些化合物可用作抗血管生成抑制剂。这些化合物的合成成本低廉，并表现出出乎意料的良好的抗血管生成活性。本发明还涉及使用香豆素及其类似物作为抗肿瘤/抗癌剂，以及治疗一些与血管生成有关的疾病或病态，包括血管生成性皮肤病如牛皮癣、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等等，以及慢性炎症性疾病如关节炎。
• Nitrogenous heterocyclic derivative and organic elecrtroluminescent element employing the same
  申请人：Yamamoto Hiroshi

  公开号：US20060154105A1

  公开（公告）日：2006-07-13

  A specific derivative of heterocyclic compound having nitrogen atom and an organic electroluminescence device comprising the compound. An organic electroluminescence device comprising at least one of organic compound layers including a light emitting layer sandwiched between an anode and a cathode, wherein said at least one of the organic compound layers comprises the derivative of the heterocyclic compound having nitrogen atom as a sole component or as mixed component. The organic electroluminescence device achieves elevation of luminance and excellent efficiency of light emission, and also achieves long lifetime by an improvement of an electrode adhesion.

  一种具有氮原子的杂环化合物的特定衍生物，以及包括该化合物的有机电致发光装置。该有机电致发光装置包括至少一个有机化合物层，其中包括在阳极和阴极之间的发光层，其中该至少一个有机化合物层包括作为唯一组分或混合组分的具有氮原子的杂环化合物的衍生物。该有机电致发光装置实现了亮度的提高和优秀的发光效率，并通过改善电极粘附实现了长寿命。
• NITROGENOUS HETEROCYCLIC DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT EMPLOYING THE SAME
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：EP1582516A1

  公开（公告）日：2005-10-05

  A specific derivative of heterocyclic compound having nitrogen atom and an organic electroluminescence device comprising the compound. An organic electroluminescence device comprising at least one of organic compound layers including a light emitting layer sandwiched between an anode and a cathode, wherein said at least one of the organic compound layers comprises the derivative of the heterocyclic compound having nitrogen atom as a sole component or as mixed component. The organic electroluminescence device achieves elevation of luminance and excellent efficiency of light emission, and also achieves long lifetime by an improvement of an electrode adhesion.

  一种具有氮原子的杂环化合物的特定衍生物和一种包含该化合物的有机电致发光器件。一种有机电致发光器件，包括至少一个有机化合物层，其中包括夹在阳极和阴极之间的发光层，其中所述至少一个有机化合物层包括作为唯一成分或混合成分的具有氮原子的杂环化合物的衍生物。该有机电致发光器件不仅提高了亮度和发光效率，还通过改善电极附着力延长了使用寿命。
• TEWARI, R. S.;AWASTHI, A. K., INDIAN J. CHEM., 1981, 20, N 2, 168-169
  作者：TEWARI, R. S.、AWASTHI, A. K.

  DOI：——

  日期：——