3,4-dihydroxy-4'-methylchalcone

• 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: 3,4-dihydroxy-4'-methylchalcone
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-1-(p-tolyl)prop-2-en-1-one；3-(3,4-Dihydroxy-phenyl)-1-p-tolyl-propenone；(E)-3-(3,4-dihydroxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: XWTFLDJHWKPIDX-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

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 3,4-dihydroxy-4'-methylchalcone
  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。
• [EN] COMPOSITION FOR TREATMENT, PREVENTION, OR AMELIORATION OF LYMPHEDEMA<br/>[FR] COMPOSITION POUR LE TRAITEMENT, LA PRÉVENTION OU L'AMÉLIORATION DU LYMPHŒDÈME<br/>[KO] 림프부종의 치료, 예방 또는 개선용 조성물
  申请人：GYEONGGIDO BUSINESS & SCIENCE ACCELERATOR

  公开号：WO2021210925A1

  公开（公告）日：2021-10-21

  본 발명은 림프부종의 치료, 예방 또는 개선 효과를 나타내는 신규 화합물, 및 이를 유효성분으로 포함하는 조성물에 관한 것으로서, 의약품, 기능성 식품 또는 식품보충제, 또는 화장품으로 적용될 수 있다. 본 발명에 따른 유효성분 화합물은 TNFα 생성 억제 활성, 대사 안정성, 가용성, 혈액 노출 등 다양한 측면에서 림프부종에 대해 현저하게 개선된 효과를 나타낸다.
• 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors
  作者：Satoshi Sogawa、Yasunori Nihro、Hiroki Ueda、Akihiro Izumi、Tokutaro Miki、Hitoshi Matsumoto、Toshio Satoh

  DOI：10.1021/jm00076a019

  日期：1993.11

  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.