(E)-4-(3-(2-(benzyloxy)phenyl)-3-oxoprop-1-en-1-yl)benzoic acid | 65786-23-4

• 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)phenyl)-3-oxoprop-1-en-1-yl)benzoic acid
• 英文别名: 4-[(E)-3-oxo-3-(2-phenylmethoxyphenyl)prop-1-enyl]benzoic acid
• CAS: 65786-23-4
• 化学式: C₂₃H₁₈O₄
• 分子量: 358.394
• InChiKey: ADMBFEMBJMDZNV-NTCAYCPXSA-N

物化性质

• 熔点：
  140.1-141.5 °C
• 沸点：
  591.2±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-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)phenyl)-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。
• 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.
• Evaluation and Optimization of the Anti-Melanogenic Activity of 1-(2-Cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone Derivatives
  作者：Byung-Hak Kim、Soo-Nam Hong、Sang-Kyu Ye、Jung-Youl Park

  DOI：10.3390/molecules24071372

  日期：——

  The chemical modification and optimization of biologically active compounds are essential steps in the identification of promising lead compounds for drug development. We previously reported the anti-melanogenic activity of 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone (chalcone 21). In this study, we synthesized 21 derivatives of chalcone 21 and evaluated their anti-melanogenic activity in -MSH-induced B16F10 cells. (E)-N-(4-(3-(2-(Cyclohexylmethoxy)phenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide (chalcone 21-21) exhibited the strongest inhibition of cellular melanin production, with an IC50 value of 0.54 M. It was more potent than chalcone 21 and the known anti-melanogenic agents kojic acid and arbutin, whose IC50 values were 4.9, 38.5, and 148.4 M, respectively. Chalcone 21-21 decreased the expression and activity of tyrosinase. It also decreased the expression of TRP1, TRP2 and MITF, the phosphorylation of CREB and ERK1/2, and the transcriptional activity of MITF and CRE. Our results demonstrate that chalcone-21-21 is an effective lead compound with anti-melanogenic activity.

  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。