(E)-3-(3,4-dihydroxyphenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one

• 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: (E)-3-(3,4-dihydroxyphenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: 2',4'-dimethoxy-3,4-dihydroxychalcone；3,4-dihydroxy-2',4'-dimethoxychalcone；3,4-Dihydroxy-2',4'-dimethoxy chalcone；3-(3,4-Dihydroxyphenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: XEFNHJDWTZIITP-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二(四氢吡喃-2-氧基)苯甲醛 在 barium dihydroxide 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 (E)-3-(3,4-dihydroxyphenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 6-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.

  DOI：

  10.1021/jm00076a019

文献信息

• Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema
  作者：Kangsan Roh、Jung-hun Lee、Hee Kang、Kye Won Park、Youngju Song、Sukchan Lee、Jin-Mo Ku

  DOI：10.1016/j.ejmech.2020.112280

  日期：2020.7

  factor α (TNF-α) production. Butein derivatives were synthesized and evaluated to identify compounds with in vitro anti-inflammatory activity. Among them, 20 μM of compounds 7j, 7m, and 14a showed 50% suppression of TNF-α production in mouse peritoneal macrophages after lipopolysaccharide stimulation. Compound 14a, exhibited the strongest potency with an in vitro IC50 of 14.6 μM and suppressed limb

  在本文中，我们证明，butein（1）可以通过抑制肿瘤坏死因子α（TNF-α）的产生来预防小鼠淋巴水肿模型中的肿胀。合成并评估了Butein衍生物，以鉴定具有体外抗炎活性的化合物。其中，20μM化合物7j，7m和14a在脂多糖刺激后表现出50％的抑制小鼠腹膜巨噬细胞TNF-α产生的作用。在鼠淋巴水肿模型中，化合物14a表现出最强的效力，体外IC50为14.6μM，肢体体积抑制了70％。在药代动力学研究中，通过口服给药，前药策略使化合物1的动力学溶解度增加了6倍，血液中的活性代谢产物水平提高了5倍，从而使化合物14a处于血液中。
• Remedies
  申请人：——

  公开号：US20030144316A1

  公开（公告）日：2003-07-31

  The present invention provides a therapeutic agent or prophylactic agent for a disease that requires enhancement of nerve growth factor production, an enhancer for nerve growth factor production, or a food, beverage or feed for enhancing nerve growth factor production, each comprising as an effective ingredient a specified compound or a salt thereof having enhancing activity for nerve growth factor production; a method for enhancing nerve growth factor production, comprising administering to a mammal the above-mentioned compound or a salt thereof; and use of the above-mentioned compound or a salt thereof in the preparation of a therapeutic agent or prophylactic agent for a disease that requires enhancement of nerve growth factor production, an enhancer for nerve growth factor production, or a food, beverage or feed for enhancing nerve growth factor production. In addition, the present invention provides novel compounds having enhancing activity for nerve growth factor production.

  本发明提供了一种治疗剂或预防剂，用于需要增强神经生长因子产生的疾病，用于增强神经生长因子产生的增强剂，或用作增强神经生长因子产生的食品、饮料或饲料，每种包含一种有效成分，即具有增强神经生长因子产生活性的指定化合物或其盐；一种增强神经生长因子产生的方法，包括向哺乳动物投与上述化合物或其盐；以及使用上述化合物或其盐制备需要增强神经生长因子产生的疾病的治疗剂或预防剂，增强神经生长因子产生的增强剂，或用于增强神经生长因子产生的食品、饮料或饲料。此外，本发明提供了具有增强神经生长因子产生活性的新化合物。
• REMEDIES
  申请人：TAKARA BIO INC.

  公开号：EP1254658A1

  公开（公告）日：2002-11-06

  The present invention provides a therapeutic agent or prophylactic agent for a disease that requires enhancement of nerve growth factor production, an enhancer for nerve growth factor production, or a food, beverage or feed for enhancing nerve growth factor production, each comprising as an effective ingredient a specified compound or a salt thereof having enhancing activity for nerve growth factor production; a method for enhancing nerve growth factor production, comprising administering to a mammal the above-mentioned compound or a salt thereof; and use of the above-mentioned compound or a salt thereof in the preparation of a therapeutic agent or prophylactic agent for a disease that requires enhancement of nerve growth factor production, an enhancer for nerve growth factor production, or a food, beverage or feed for enhancing nerve growth factor production. In addition, the present invention provides novel compounds having enhancing activity for nerve growth factor production.

  本发明提供了一种用于需要增强神经生长因子产生的疾病的治疗剂或预防剂，一种用于增强神经生长因子产生的增强剂，或一种用于增强神经生长因子产生的食品、饮料或饲料，每一种都包含作为有效成分的具有增强神经生长因子产生活性的特定化合物或其盐；一种增强神经生长因子生成的方法，包括向哺乳动物施用上述化合物或其盐；以及上述化合物或其盐在制备需要增强神经生长因子生成的疾病的治疗剂或预防剂、神经生长因子生成增强剂或增强神经生长因子生成的食品、饮料或饲料中的用途。此外，本发明还提供了具有增强神经生长因子生成活性的新型化合物。
• Chalcone derivatives as xanthine oxidase inhibitors: synthesis, binding mode investigation, biological evaluation, and ADMET prediction
  作者：Can Yang、Yi Liu、Yanbei Tu、Lizi Li、Jiana Du、Dehong Yu、Pei He、Tao Wang、Yan Liu、Hao Chen、Yanfang Li

  DOI：10.1016/j.bioorg.2022.106320

  日期：2023.2
• REMEDIES FOR THE TREATMENT OF NERVE DIORDERS
  申请人：TAKARA BIO INC.

  公开号：EP1254658B1

  公开（公告）日：2008-09-24