(E)-3-(3,4-二羟基苯基)-1-(2,5-二甲氧基苯基)丙-2-烯-1-酮 | 152809-88-6

• 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
• 中文名称: (E)-3-(3,4-二羟基苯基)-1-(2,5-二甲氧基苯基)丙-2-烯-1-酮
• 英文名称: 2',5'-dimethoxy-3,4-dihydroxychalcone
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-1-(2,5-dimethoxyphenyl)prop-2-en-1-one
• CAS: 152809-88-6
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: FFUVITXFNNXCPG-ZZXKWVIFSA-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 24.0h， 生成 (E)-3-(3,4-二羟基苯基)-1-(2,5-二甲氧基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  查耳酮的合成及其抗炎作用。

  摘要：

  肥大细胞和嗜中性粒细胞脱粒的过程导致炎症性疾病。小胶质细胞和巨噬细胞的活化被认为与中枢神经系统的炎性，感染性和变性疾病有关。结合肥大细胞或嗜中性粒细胞脱粒以及活化的小胶质细胞或巨噬细胞脱颗粒所释放的化学介质的有效抑制作用，将产生一种有前途的抗炎药，用于治疗周围和中枢炎症。据报道，一系列查尔酮衍生物具有有效的抗炎活性。为了不断开发有效的抗炎药，合成了一系列新的查耳酮，2'-羟基和2'，5'-二羟基查尔酮，它们对肥大细胞，嗜中性粒细胞，体外评估了小胶质细胞和巨噬细胞。查耳酮通过适当的苯乙酮与适当的芳族醛的克莱森-施密特缩合制备。用合适的羟基查耳酮和烷基碘制备烷氧基查耳酮，通过用Pd / C氢化合适的查耳酮来制备二羟基查耳酮。几乎所有羟基查耳酮均对用甲酰-Met-Leu-Phe /细胞松弛素B（fMLP / CB）刺激的大鼠中性粒细胞释放β-葡萄糖醛酸苷酶和溶菌酶具有有效的抑制作用。在羟基查耳酮中，化合物1是用fMLP

  DOI：

  10.1211/0022357001773814

文献信息

• 3,4-dihydroxychalcone derivatives
  申请人：Nippon Hypox Laboratories Incorporated

  公开号：US05276058A1

  公开（公告）日：1994-01-04

  Novel 3,4-dihydroxychalcone derivatives useful as a pharmaceutical material, and novel anti-inflammatory preparations. The 3,4-dihydroxychalcone derivatives are compounds of the formula [I], ##STR1## wherein X is a substituted phenyl group represented, e.g., by the formula (i), ##STR2## in which R.sup.1 is a hydrogen atom or an alkyl group and R.sup.2 is an alkyl group, an alkoxy group or an --OH group (excluding an OH-group in the 4-position) or salts thereof. The anti-inflammatory preparations contain one of the above 3,4-dihydroxychalcone derivatives as an active ingredient.

  小说3,4-二羟基查尔酮衍生物可用作制药材料和新型抗炎制剂。3,4-二羟基查尔酮衍生物是公式[I]的化合物，其中X是一个取代的苯基，例如，由公式(i)表示，其中R1是氢原子或烷基，R2是烷基，烷氧基或--OH基（不包括4-位的OH基）或其盐。抗炎制剂包含上述任一3,4-二羟基查尔酮衍生物作为活性成分。
• 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.
• 3,4-Dihydroxychalcone derivatives
  申请人：NIPPON HYPOX LABORATORIES INCORPORATED

  公开号：EP0629602B1

  公开（公告）日：1997-09-10
• Use of Ltb4 Inhibitors for the Treatment of B-Cell Leukemias and Lymphomas
  申请人：Claesson Hans-Erik

  公开号：US20080081835A1

  公开（公告）日：2008-04-03

  The invention relates to the use of an inhibitor of the biosynthesis and/or function of LTB 4 for the manufacture of a medicament for the treatment of B-cell chronic lymphocytic leukemia (B-CLL), B-prolymphocytic leukemia (B-PLL) or B-cell lymphoma. Preferably, the inhibitor of the biosynthesis and/or function of LTB 4 is the inhibitor of 5-LO BWA4C or the inhibitor of FLAP MK-886.
• Method and composition for treating inflammatory disorders
  申请人：Pereswetoff-Morath Lena

  公开号：US20090220583A1

  公开（公告）日：2009-09-03

  There is provided homogeneous pharmaceutical compositions for the treatment of inflammatory disorders comprising an antiinflammatory and/or antihistaminic active ingredient, a polar lipid liposome and a pharmaceutically-acceptable aqueous carrier.