(E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid | 919092-38-9

• 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)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid
• 英文别名: 4-[(E)-3-[2-(cyclohexylmethoxy)-6-hydroxyphenyl]-3-oxoprop-1-enyl]benzoic acid
• CAS: 919092-38-9
• 化学式: C₂₃H₂₄O₅
• 分子量: 380.441
• InChiKey: HRMWEWKYVKNTTO-SDNWHVSQSA-N

物化性质

• 熔点：
  213.8-214.9 °C
• 沸点：
  625.0±55.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、137.89 kPa 条件下， 反应 2.0h， 以77%的产率得到4-[3-[2-(Cyclohexylmethoxy)-6-hydroxyphenyl]-3-oxopropyl]benzoic acid
  参考文献：
  名称：

  Structural requirement of chalcones for the inhibitory activity of interleukin-5

  摘要：

  Novel chalcones were found as potent inhibitors of interleukin (IL)-5. 1-(2-Benzyloxy-6-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one (2b, 78.8% inhibition at 50 mu M, IC50 = 25.3 mu M) was initially identified as a potent inhibitor of IL-5. This shows the compatible activity with budesonide or sophoricoside. To identify structural requirements, 26 chalcones were prepared and their inhibitory activities were tested against IL-5. Among them, compound 4-[(E)-3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzenesulfonamide (2w, 99.5% inhibition at 50 mu M, IC50 = 1-8 mu M) shows the most potent activity. The important structural requirements of these chalcone analogs exhibiting the inhibitory activity against IL-5 were recognized as the following. (1) The hydrophobic group such as benzyloxy or cyclohexylmethoxy at 6-position of A ring is necessary. (2) The existence of phenolic hydroxyl at 6-position of A ring is critical. (3) Propenone unit as alpha,beta-unsaturated ketone is essential. (4) Electron withdrawing groups with hydrogen acceptor property at 4-position of B ring enhance the activity and quantitative structure-activity relationship of 2 regarding these substituents was determined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.007
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 3.75h， 生成 (E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid
  参考文献：
  名称：

  Structural requirement of chalcones for the inhibitory activity of interleukin-5

  摘要：

  Novel chalcones were found as potent inhibitors of interleukin (IL)-5. 1-(2-Benzyloxy-6-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one (2b, 78.8% inhibition at 50 mu M, IC50 = 25.3 mu M) was initially identified as a potent inhibitor of IL-5. This shows the compatible activity with budesonide or sophoricoside. To identify structural requirements, 26 chalcones were prepared and their inhibitory activities were tested against IL-5. Among them, compound 4-[(E)-3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzenesulfonamide (2w, 99.5% inhibition at 50 mu M, IC50 = 1-8 mu M) shows the most potent activity. The important structural requirements of these chalcone analogs exhibiting the inhibitory activity against IL-5 were recognized as the following. (1) The hydrophobic group such as benzyloxy or cyclohexylmethoxy at 6-position of A ring is necessary. (2) The existence of phenolic hydroxyl at 6-position of A ring is critical. (3) Propenone unit as alpha,beta-unsaturated ketone is essential. (4) Electron withdrawing groups with hydrogen acceptor property at 4-position of B ring enhance the activity and quantitative structure-activity relationship of 2 regarding these substituents was determined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.007

文献信息

• WO2008/18692
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] NOVEL CHALCONE DERIVATIVES WHICH INHIBIT THE IL-5 ACTIVITY<br/>[FR] NOUVEAUX DÉRIVÉS DE CHALCONE QUI INHIBENT L'ACTIVITÉ DE L'IL-5
  申请人：INDUSTRY AND ACADEMIC COOPERAT

  公开号：WO2008018692A1

  公开（公告）日：2008-02-14

  [EN] Disclosed herein are novel chalcone derivatives, which are low-molecular nonpeptide substances as interleukin-5 (IL-5) inhibitors having the effect of treating chronic allergic diseases, as well as a preparation method thereof and the use thereof as IL-5 inhibitors. Because the novel chalcone derivatives are low-molecular nonpeptide substances, they have no nonspecific response to proteins, unlike the prior known agents for treating allergic inflammation, and thus will be useful as allergy inhibitors.
  [FR] La présente invention concerne de nouveaux dérivés de chalcone, qui sont des substances non peptidiques de faible masse moléculaire telles que des inhibiteurs de l'interleukine-5 (IL-5), ayant la capacité de traiter des maladies allergiques chroniques, de même qu'elle concerne leur procédé de préparation et leur utilisation en tant qu'inhibiteurs de l'IL-5. Étant donné que les nouveaux dérivés de chalcone sont des substances non peptidiques de faible masse moléculaire, ils ne déclenchent pas de réponse non spécifique contre les protéines, contrairement aux agents de traitement d'inflammation allergique connus antérieurement, et ils se révèlent par conséquent utiles en tant qu'inhibiteurs d'allergies.
• Structural requirement of chalcones for the inhibitory activity of interleukin-5
  作者：Hyun-Mo Yang、Hye-Rim Shin、Soo-Hyun Cho、Seong-Cheol Bang、Gyu-Yong Song、Jung-Hun Ju、Mi-Kyeong Kim、Seung-Ho Lee、Jae-Chun Ryu、Youngsoo Kim

  DOI：10.1016/j.bmc.2006.10.007

  日期：2007.1.1

  Novel chalcones were found as potent inhibitors of interleukin (IL)-5. 1-(2-Benzyloxy-6-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one (2b, 78.8% inhibition at 50 mu M, IC50 = 25.3 mu M) was initially identified as a potent inhibitor of IL-5. This shows the compatible activity with budesonide or sophoricoside. To identify structural requirements, 26 chalcones were prepared and their inhibitory activities were tested against IL-5. Among them, compound 4-[(E)-3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzenesulfonamide (2w, 99.5% inhibition at 50 mu M, IC50 = 1-8 mu M) shows the most potent activity. The important structural requirements of these chalcone analogs exhibiting the inhibitory activity against IL-5 were recognized as the following. (1) The hydrophobic group such as benzyloxy or cyclohexylmethoxy at 6-position of A ring is necessary. (2) The existence of phenolic hydroxyl at 6-position of A ring is critical. (3) Propenone unit as alpha,beta-unsaturated ketone is essential. (4) Electron withdrawing groups with hydrogen acceptor property at 4-position of B ring enhance the activity and quantitative structure-activity relationship of 2 regarding these substituents was determined. (c) 2006 Elsevier Ltd. All rights reserved.