2,6-Dichloro-2',6'-dimethoxychalcone | 346702-10-1

• 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: 2,6-Dichloro-2',6'-dimethoxychalcone
• 英文别名: 3-(2,6-dichlorophenyl)-1-(2,6-dimethoxyphenyl)prop-2-en-1-one
• CAS: 346702-10-1
• 化学式: C₁₇H₁₄Cl₂O₃
• 分子量: 337.202
• InChiKey: VBBBZHZBQBUNOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二甲氧基苯乙酮 、 2,6-二氯苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以87%的产率得到2,6-Dichloro-2',6'-dimethoxychalcone
  参考文献：
  名称：

  A Synthetic Chalcone as a Potent Inducer of Glutathione Biosynthesis

  摘要：

  Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2',5'-dihydroxychalcone (2',5'-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F andCl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4',6'-dimethoxy-2'-hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.

  DOI：

  10.1021/jm2016073

文献信息

• Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：University of Georgia Research Foundation, Inc.

  公开号：US20030027830A1

  公开（公告）日：2003-02-06

  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, incluidng angiongenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及茉莉酮及其衍生物和类似物，其可用作抗血管生成抑制剂。这些廉价合成的化合物表现出出乎意料的良好的抗血管生成抑制活性。本发明还涉及将茉莉酮及其类似物用作抗肿瘤/抗癌剂，以及用于治疗许多与血管生成有关的疾病或病态，包括血管生成性皮肤疾病，如牛皮癣、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等，以及慢性炎症性疾病，如关节炎。
• Chalcone and its analogs as agents for the inhibition of angiogensis and related disease states
  申请人：The University of Georgia Research Foundation, Inc.

  公开号：US06462075B1

  公开（公告）日：2002-10-08

  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, incluidng angiongenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及具有抑制血管生成作用的查尔酮及其衍生物和类似物。这些成分可以廉价合成，并表现出出乎意料的良好的抑制血管生成活性。本发明还涉及使用查尔酮及其类似物作为抗肿瘤/抗癌剂，并用于治疗多种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。
• A Synthetic Chalcone as a Potent Inducer of Glutathione Biosynthesis
  作者：Remy Kachadourian、Brian J. Day、Subbiah Pugazhenti、Christopher C. Franklin、Estelle Genoux-Bastide、Gregory Mahaffey、Charlotte Gauthier、Attilio Di Pietro、Ahcène Boumendjel

  DOI：10.1021/jm2016073

  日期：2012.2.9

  Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2',5'-dihydroxychalcone (2',5'-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F andCl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4',6'-dimethoxy-2'-hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.