[2,3-dimethyl-4-(1-oxopropyl)phenoxy]acetic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2,3-dimethyl-4-(1-oxopropyl)phenoxy]acetic acid
• 英文别名: 2-(2,3-Dimethyl-4-propanoylphenoxy)acetic acid
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: JARJRBBNCJISNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2,3-dimethyl-4-(1-oxopropyl)phenoxy]acetic acid 、 聚合甲醛 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  乙炔酸类似物的合成及其对谷胱甘肽-s-转移酶P1-1活性抑制的构效关系。

  摘要：

  乙二酸（EA）是谷胱甘肽S-转移酶pi（GSTP1-1）抑制剂。设计和合成了十五种EA类似物，并在人白血病HL-60细胞的裂解物中测试了它们对GSTP1-1活性的抑制作用。这些化合物使用取代的苯酚作为前体，通过与2-氯羧酸反应并酰化而合成。结构活性分析表明，在3'位甲基，溴化物和氟化物替代EA的氯化物仍然具有GSTP1-1抑制作用。在3'位没有任何取代基的化合物失去了对GSTP1-1抑制的活性。这些数据表明，EA 3'位置的取代对于抑制GSTP1-1活性是必需的。

  DOI：

  10.1016/j.bmc.2005.03.046
• 作为产物：
  描述：

  二甲酚 在 二硫化碳 、 aluminum (III) chloride 、 sodium hydroxide 作用下， 生成 [2,3-dimethyl-4-(1-oxopropyl)phenoxy]acetic acid
  参考文献：
  名称：

  Inhibitory effects of ethacrynic acid analogues lacking the α,β-unsaturated carbonyl unit and para-acylated phenols on human cancer cells

  摘要：

  A series of ethacrynic acid analogues, lacking the alpha,beta-unsaturated carbonyl unit, was synthesized and subsequently evaluated for their ability to inhibit the migration of human breast cancer cells, Hs578Ts(i) 8 as well as of human prostate cancer cells, C4-2B. These cell lines provide a good model system to study migration and invasion, since they represent metastatic cancer. Our studies show that ethacrynic acid analogues with methyl substituents at the aromatic ring demonstrate no inhibitory effect on the migration of both cancer cell lines, whereas a precursor in the synthesis of these ethacrynic acid analogues (II-1, a para-acylated m-cresol) is an excellent inhibitor of the migration of both cancer cell lines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.074

文献信息

• Novel Oxadiazole Analogues Derived from Ethacrynic Acid: Design, Synthesis, and Structure−Activity Relationships in Inhibiting the Activity of Glutathione <i>S</i>-Transferase P1-1 and Cancer Cell Proliferation
  作者：Xinmei Yang、Guyue Liu、Hongcai Li、Yun Zhang、Dandan Song、Chunmin Li、Rui Wang、Bo Liu、Wen Liang、Yongkui Jing、Guisen Zhao

  DOI：10.1021/jm9011565

  日期：2010.2.11

  P1-1) inhibitor with weak antiproliferative ability in tumor cells. By use of the principle of bioisosterism, a series of novel EA oxadiazole analogues were designed and synthesized. The structure−activity relationships of inhibiting GST P1-1 activity and cell proliferation of those EA analogues were investigated in human leukemia HL-60 cells. Our data revealed that those EA oxadiazole analogues had improved

  乙二酸（EA）是一种谷胱甘肽S-转移酶P1-1（GST P1-1）抑制剂，在肿瘤细胞中具有较弱的抗增殖能力。利用生物立体异构原理，设计并合成了一系列新型的EA恶二唑类似物。在人白血病HL-60细胞中研究了抑制GST P1-1活性与那些EA类似物的细胞增殖的构效关系。我们的数据显示，那些EA恶二唑类似物具有更好的抗增殖活性，并且大多数与EA相比对GST P1-1活性具有相似或更好的抑制作用。化合物6u是有效的抗增殖剂之一，没有抑制GST P1-1活性。化合物6r和6s在几种实体瘤细胞系中是两种有效的细胞生长抑制剂，其浓度可抑制一半的细胞生长，其浓度低于5μM。我们的数据表明，这些EA恶二唑类似物是有望通过GST P1-1抑制依赖性和/或非依赖性途径发挥作用的抗肿瘤药物。
• Synthesis and structure–activity relationship of ethacrynic acid analogues on glutathione-s-transferase P1-1 activity inhibition
  作者：Guisen Zhao、Tao Yu、Rui Wang、Xiaobing Wang、Yongkui Jing

  DOI：10.1016/j.bmc.2005.03.046

  日期：2005.6

  Ethacrynic acid (EA) is a glutathione-s-transferase pi (GSTP1-1) inhibitor. Fifteen of EA analogues were designed and synthesized and their inhibition on GSTP1-1 activity was tested in lysate of human leukemia HL-60 cells. These compounds were synthesized using substituted phenol as precursors through reacting with 2-chlorocarboxylic acid and acylation. Structure-activity analysis indicates that replacements

  乙二酸（EA）是谷胱甘肽S-转移酶pi（GSTP1-1）抑制剂。设计和合成了十五种EA类似物，并在人白血病HL-60细胞的裂解物中测试了它们对GSTP1-1活性的抑制作用。这些化合物使用取代的苯酚作为前体，通过与2-氯羧酸反应并酰化而合成。结构活性分析表明，在3'位甲基，溴化物和氟化物替代EA的氯化物仍然具有GSTP1-1抑制作用。在3'位没有任何取代基的化合物失去了对GSTP1-1抑制的活性。这些数据表明，EA 3'位置的取代对于抑制GSTP1-1活性是必需的。
• Inhibitory effects of ethacrynic acid analogues lacking the α,β-unsaturated carbonyl unit and para-acylated phenols on human cancer cells
  作者：Zack E. Bryant、Romy F.J. Janser、Medina Jabarkhail、Melissa S. Candelaria-Lyons、Brittni B. Romero、Severine Van slambrouck、Wim F.A. Steelant、Ingo Janser

  DOI：10.1016/j.bmcl.2010.12.074

  日期：2011.2

  A series of ethacrynic acid analogues, lacking the alpha,beta-unsaturated carbonyl unit, was synthesized and subsequently evaluated for their ability to inhibit the migration of human breast cancer cells, Hs578Ts(i) 8 as well as of human prostate cancer cells, C4-2B. These cell lines provide a good model system to study migration and invasion, since they represent metastatic cancer. Our studies show that ethacrynic acid analogues with methyl substituents at the aromatic ring demonstrate no inhibitory effect on the migration of both cancer cell lines, whereas a precursor in the synthesis of these ethacrynic acid analogues (II-1, a para-acylated m-cresol) is an excellent inhibitor of the migration of both cancer cell lines. (C) 2010 Elsevier Ltd. All rights reserved.