[3-methyl-4-(1-oxo-propyl)phenoxy]ethanoic acid | 1006585-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-methyl-4-(1-oxo-propyl)phenoxy]ethanoic acid
• 英文别名: 2-(3-Methyl-4-propanoylphenoxy)acetic acid
• CAS: 1006585-37-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: DMJPVYQQSUUSIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  [3-methyl-4-(1-oxo-propyl)phenoxy]ethanoic acid 、 聚合甲醛 在 potassium carbonate 作用下， 以27.3%的产率得到2-[3-Methyl-4-(2-methylprop-2-enoyl)phenoxy]acetic acid
  参考文献：
  名称：

  The synthesis of α,β-unsaturated carbonyl derivatives with the ability to inhibit both glutathione S-transferase P1-1 activity and the proliferation of leukemia cells

  摘要：

  Ethacrynic acid (EA), an alpha,beta-unsaturated carbonyl compound, is a glutathione S-transferase P1-1 (GSTP1-1) inhibitor. Twenty-one novel EA derivatives have been synthesized. The effects of these compounds on GSTP1-1 activity and on the proliferation of human leukemia HL-60 cells have been determined. Compounds with a halogen substitution at the 3'-position of the aromatic ring have greater inhibitory effects on GSTP1-1 activity than those of compounds with a methyl substitution there. Compounds with substitutions at both the 2'- and 3'-positions of the aromatic ring have more antiproliferative ability than those with one substitution at 3'-position. Esterification of the carboxyl group appears to increase the antiproliferative ability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.037
• 作为产物：
  描述：

  碘乙酸 、 1-(4-hydroxy-2-methylphenyl)propan-1-one 在 sodium hydroxide 、 盐酸 作用下， 生成 [3-methyl-4-(1-oxo-propyl)phenoxy]ethanoic acid
  参考文献：
  名称：

  Ethacrynic acid analogues lacking the α,β-unsaturated carbonyl unit—Potential anti-metastatic drugs

  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, MCF-7/AZ. Several of the analogues were already active in the low micromolar range, whereas ethacrynic acid itself shows no potential to inhibit the migration of these cancer cells. Preliminary studies show that the presence of one or more methoxy groups at the phenyl ring of ethacrynic acid is important in order for the ethacrynic acid analogues to demonstrate an inhibitory effect on the migration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.144

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。
• Ethacrynic acid analogues lacking the α,β-unsaturated carbonyl unit—Potential anti-metastatic drugs
  作者：Romy F.J. Janser、Ranjith K. Meka、Zack E. Bryant、Enoch A. Adogla、Elizabeth K. Vogel、Jaimie L. Wharton、Cynthia M. Tilley、Catherine N. Kaminski、Seth L. Ferrey、Severine Van slambrouck、Wim F.A. Steelant、Ingo Janser

  DOI：10.1016/j.bmcl.2010.01.144

  日期：2010.3

  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, MCF-7/AZ. Several of the analogues were already active in the low micromolar range, whereas ethacrynic acid itself shows no potential to inhibit the migration of these cancer cells. Preliminary studies show that the presence of one or more methoxy groups at the phenyl ring of ethacrynic acid is important in order for the ethacrynic acid analogues to demonstrate an inhibitory effect on the migration. (C) 2010 Elsevier Ltd. All rights reserved.
• The synthesis of α,β-unsaturated carbonyl derivatives with the ability to inhibit both glutathione S-transferase P1-1 activity and the proliferation of leukemia cells
  作者：Guisen Zhao、Chuan Liu、Rui Wang、Dandan Song、Xiaobing Wang、Hongxiang Lou、Yongkui Jing

  DOI：10.1016/j.bmc.2007.01.037

  日期：2007.4

  Ethacrynic acid (EA), an alpha,beta-unsaturated carbonyl compound, is a glutathione S-transferase P1-1 (GSTP1-1) inhibitor. Twenty-one novel EA derivatives have been synthesized. The effects of these compounds on GSTP1-1 activity and on the proliferation of human leukemia HL-60 cells have been determined. Compounds with a halogen substitution at the 3'-position of the aromatic ring have greater inhibitory effects on GSTP1-1 activity than those of compounds with a methyl substitution there. Compounds with substitutions at both the 2'- and 3'-positions of the aromatic ring have more antiproliferative ability than those with one substitution at 3'-position. Esterification of the carboxyl group appears to increase the antiproliferative ability. (c) 2007 Elsevier Ltd. All rights reserved.