2-[2,3-dimethyl-4-(1-oxopropyl)phenoxy]propionic acid | 858371-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2,3-dimethyl-4-(1-oxopropyl)phenoxy]propionic acid
• 英文别名: 2-(2,3-Dimethyl-4-propanoylphenoxy)propanoic acid；2-(2,3-dimethyl-4-propanoylphenoxy)propanoic acid
• CAS: 858371-32-1
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: PTZXXEGPIJYFPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-[2,3-dimethyl-4-(1-oxopropyl)phenoxy]propionic acid 在 potassium carbonate 、 对甲苯磺酸 作用下， 反应 0.67h， 生成 Methyl 2-[2,3-dimethyl-4-(2-methylprop-2-enoyl)phenoxy]propanoate
  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：

  二甲酚 在 sodium hydroxide 、 三氯化铝 作用下， 以 二硫化碳 为溶剂， 生成 2-[2,3-dimethyl-4-(1-oxopropyl)phenoxy]propionic 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

文献信息

• 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。
• 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.