(E)-4-(3-(2-(benzyloxy)-6-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzoic acid

• 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-(benzyloxy)-6-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzoic acid
• 英文别名: 4-[(E)-3-(2-hydroxy-6-phenylmethoxyphenyl)-3-oxoprop-1-enyl]benzoic acid
• 化学式: C₂₃H₁₈O₅
• 分子量: 374.393
• InChiKey: XKCPQUHLOUJTTQ-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基-6-苄氧基苯乙酮 、 对醛基苯甲酸 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-4-(3-(2-(benzyloxy)-6-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzoic acid
  参考文献：
  名称：

  Evaluation and Optimization of the Anti-Melanogenic Activity of 1-(2-Cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone Derivatives

  摘要：

  生物活性化合物的化学修饰和优化是药物开发中寻找有前途的先导化合物的关键步骤。我们先前报告了1-(2-环己基甲氧基-6-羟基苯基)-3-(4-羟甲基苯基)-丙酮（查尔酮21）的抗黑色素生成活性。在本研究中，我们合成了21个查尔酮21衍生物，并在-MSH诱导的B16F10细胞中评估了它们的抗黑色素生成活性。N-(4-(3-(2-（环己基甲氧基）苯基）-3-氧代丙-1-烯-1-基）苯乙酰胺（查尔酮21-21）表现出最强的细胞黑色素生成抑制作用，其IC50值为0.54 M。它比查尔酮21和已知的抗黑色素生成剂曲酸和熊果苷更具潜力，它们的IC50值分别为4.9、38.5和148.4 M。查尔酮21-21降低了酪氨酸酶的表达和活性。它还降低了TRP1、TRP2和MITF的表达，CREB和ERK1/2的磷酸化，以及MITF和CRE的转录活性。我们的结果表明，查尔酮21-21是一种具有抗黑色素生成活性的有效先导化合物。

  DOI：

  10.3390/molecules24071372

文献信息

• 찰콘 유도체를 포함하는 피부 미백용 조성물
  申请人：DAEJEON UNIVERSITY Industry-University Cooperation Foundation 대전대학교 산학협력단(120080024434) Corp. No ▼ 160171-0004131BRN ▼305-82-13385

  公开号：KR20200010955A

  公开（公告）日：2020-01-31

  본 발명은 찰콘 유도체를 포함하는 피부 미백용 조성물에 관한 것으로, 멜라닌 생성을 효과적으로 억제할 수 있어, 멜라닌이 과다 침착된 피부의 미백에 유용하게 활용할 수 있다.

  这是关于包含鹰嘴豆指导剂的皮肤美白配方的发明，它可以有效地抑制黑色素的生成，因此可以有用地用于美白过度沉淀黑色素的皮肤。
• Fused heterocyclic derivative, medicinal composition containing the same, and medicinal use thereof
  申请人：Fushimi Nobuhiko

  公开号：US20060247179A1

  公开（公告）日：2006-11-02

  The present invention provides fused heterocyclic derivatives represented by the general formula: wherein R 1 represents H, halogen, OH, etc.; R 2 represents H, halogen or an alkyl group; R 3 and R 4 represent H, OH, halogen, etc.; Q represents alkylene, etc.; ring A represents aryl or heteroaryl; and G represents , or pharmaceutically acceptable salts thereof, or prodrugs thereof, which exhibit an excellent inhibitory activity in human SGLT and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications or obesity, pharmaceutical compositions comprising the same, and pharmaceutical uses thereof.

  本发明提供了由通式表示的融合杂环衍生物：其中R1代表H、卤素、OH等；R2代表H、卤素或烷基；R3和R4代表H、OH、卤素等；Q代表烷基等；环A代表芳基或杂芳基；G代表，或其药学上可接受的盐，或其前药，它们在人类SGLT中表现出优异的抑制活性，并且可用作预防或治疗与高血糖有关的疾病，如糖尿病、餐后高血糖、糖耐量受损、糖尿病并发症或肥胖症的药剂，以及它们的药用组合物和药用用途。
• FUSED HETEROCYCLIC DERIVATIVE, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL USE THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1609798B1

  公开（公告）日：2012-05-09
• 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.
• US7566699B2
  申请人：——

  公开号：US7566699B2

  公开（公告）日：2009-07-28