3-Chlor-4-propionyl-phenoxyessigsaeure | 1212-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Chlor-4-propionyl-phenoxyessigsaeure
• 英文别名: 3-Chlor-4-propionylphenoxyessigsaeure；4-Propionyl-3-chlorphenoxyessigsaeure；2-(3-Chloro-4-propanoylphenoxy)acetic acid
• CAS: 1212-38-0
• 化学式: C₁₁H₁₁ClO₄
• 分子量: 242.659
• InChiKey: LJPZUHSKOCXWOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  聚合甲醛 、 3-Chlor-4-propionyl-phenoxyessigsaeure 在 potassium carbonate 作用下， 以56.1%的产率得到3-Chlor-4-methacryloyl-phenoxyessigsaeure
  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：

  3-氯苯酚 在 sodium hydroxide 、 三氯化铝 作用下， 以 二硫化碳 为溶剂， 生成 3-Chlor-4-propionyl-phenoxyessigsaeure
  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

• 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。
• BE639727
  申请人：——

  公开号：——

  公开（公告）日：——
• BE612755
  申请人：——

  公开号：——

  公开（公告）日：——
• (2-alkylidene acyl)phenoxy-and (2-alkylidene acyl)phenylmercaptocarboxylic acids
  申请人：MERCK &

  公开号：US03255241A1

  公开（公告）日：1966-06-07