2-羟基-3-(2-甲氧基苯基)丙烯酸 | 334022-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-3-(2-甲氧基苯基)丙烯酸
• 英文名称: 2-hydroxy-3-(2-methoxyphenyl)acrylic acid
• 英文别名: 2-Hydroxy-3-(2-methoxyphenyl)prop-2-enoic acid；2-hydroxy-3-(2-methoxyphenyl)prop-2-enoic acid
• CAS: 334022-78-5
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: XPDLRZCMKJXYNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-3-(2-甲氧基苯基)丙烯酸 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 以56%的产率得到2-(hydroxyimino)-3-(2-methoxyphenyl)propanoic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP)

  摘要：

  C-terminal Binding Protein (CtBP) is a transcriptional co-regulator that downregulates the expression of many tumor-suppressor genes. Utilizing a crystal structure of CtBP with its substrate 4-methylthio-2-oxobutyric acid (MTOB) and NAD(+) as a guide, we have designed, synthesized, and tested a series of small molecule inhibitors of CtBP. From our first round of compounds, we identified 2-(hydroxyimino)-3-phenylpropanoic acid as a potent CtBP inhibitor (IC50 = 0.24 mu M). A structure-activity relationship study of this compound further identified the 4-chloro- (IC50 = 0.18 mu M) and 3-chloro- (IC50 = 0.17 mu M) analogues as additional potent CtBP inhibitors. Evaluation of the hydroxyimine analogues in a short-term cell growth/viability assay showed that the 4-chloro- and 3-chloro-analogues are 2-fold and 4-fold more potent, respectively, than the MTOB control. A functional cellular assay using a CtBP-specific transcriptional readout revealed that the 4-chloro- and 3-chloro-hydroxyimine analogues were able to block CtBP transcriptional repression activity. This data suggests that substrate-competitive inhibition of CtBP dehydrogenase activity is a potential mechanism to reactivate tumor-suppressor gene expression as a therapeutic strategy for cancer. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.037
• 作为产物：
  描述：

  2-methyl-4-(2'-methoxyphenylidene)-5-oxazolone 在 盐酸 作用下， 生成 2-羟基-3-(2-甲氧基苯基)丙烯酸
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8

文献信息

• Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide
  作者：Romain Dupont、Philippe Cotelle

  DOI：10.1016/s0040-4039(00)02011-6

  日期：2001.1

  trimethoxyphenyl-2-hydroxypropenoic acids 1a–d gave mixtures of (E) and (Z) mono, di or trihydroxyphenyl-2-hydroxypropenoic acids 2a–d when treated with boron tribromide. The isomerisation proceeds during the work-up and depends on the duration of the hydrolysis and the number of oxygens on the aromatic ring. When the aromatic ring was substituted with a methoxy group at the ortho position, a cyclisation occurs

  （Ž） -单，二或三甲氧基苯基-2- hydroxypropenoic酸1A-d得到（的混合物ë）和（Ž）单，二或三羟基苯基-2- hydroxypropenoic酸图2a-d时用三溴化硼。异构化在后处理过程中进行，并取决于水解的持续时间和芳环上的氧数。当芳环在邻位被甲氧基取代时，发生环化，并且可以获得3-羟基香豆素3和苯并呋喃-2-羧酸4。3-羟基香豆素3a 3-（2-甲氧基苯基）-2，3-环氧丙酸甲酯与三溴化硼的反应也几乎可以定量获得。
• Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols
  作者：Vincent Dalla、Philippe Cotelle、Jean Pierre Catteau

  DOI：10.1016/s0040-4039(97)00154-8

  日期：1997.3

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.
• Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP)
  作者：Sudha Korwar、Benjamin L. Morris、Hardik I. Parikh、Robert A. Coover、Tyler W. Doughty、Ian M. Love、Brendan J. Hilbert、William E. Royer、Glen E. Kellogg、Steven R. Grossman、Keith C. Ellis

  DOI：10.1016/j.bmc.2016.04.037

  日期：2016.6

  C-terminal Binding Protein (CtBP) is a transcriptional co-regulator that downregulates the expression of many tumor-suppressor genes. Utilizing a crystal structure of CtBP with its substrate 4-methylthio-2-oxobutyric acid (MTOB) and NAD(+) as a guide, we have designed, synthesized, and tested a series of small molecule inhibitors of CtBP. From our first round of compounds, we identified 2-(hydroxyimino)-3-phenylpropanoic acid as a potent CtBP inhibitor (IC50 = 0.24 mu M). A structure-activity relationship study of this compound further identified the 4-chloro- (IC50 = 0.18 mu M) and 3-chloro- (IC50 = 0.17 mu M) analogues as additional potent CtBP inhibitors. Evaluation of the hydroxyimine analogues in a short-term cell growth/viability assay showed that the 4-chloro- and 3-chloro-analogues are 2-fold and 4-fold more potent, respectively, than the MTOB control. A functional cellular assay using a CtBP-specific transcriptional readout revealed that the 4-chloro- and 3-chloro-hydroxyimine analogues were able to block CtBP transcriptional repression activity. This data suggests that substrate-competitive inhibition of CtBP dehydrogenase activity is a potential mechanism to reactivate tumor-suppressor gene expression as a therapeutic strategy for cancer. (C) 2016 Elsevier Ltd. All rights reserved.