111649-73-1

Basic information

• Product Name: 3-(4-fluorophenyl)-2-hydroxyacrylic acid
• Synonyms: 3-(4-fluorophenyl)-2-hydroxyacrylic acid
• CAS NO: 111649-73-1
• Molecular Weight: 182.151
• Mol File: 111649-73-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-(4-fluorophenyl)-2-hydroxyacrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorophenyl)-2-hydroxyacrylic acid(111649-73-1)
• EPA Substance Registry System: 3-(4-fluorophenyl)-2-hydroxyacrylic acid(111649-73-1)

Safety Data

• Hazardous Substances Data: 111649-73-1(Hazardous Substances Data)

Upstream product

• 300827-96-7 C₁₀H₇FN₂O₂ 
• 586-08-3 4-(4-fluorophenyl)methylene-2-methyl-5(4H)-oxazolone 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 1601468-81-8 2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono)-3-(4-fluorophenyl)propanoic acid 
• 1601468-80-7 2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono)-3-(4-fluorophenyl)propanoic acid 

Relevant articles and documents

Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors

Through a structure-based drug design project (SBDD), potent small molecule inhibitors of pyruvate carboxylase (PC) have been discovered. A series of α-keto acids (7) and α-hydroxycinnamic acids (8) were prepared and evaluated for inhibition of PC in two assays. The two most potent inhibitors were 3,3′-(1,4-phenylene)bis[2-hydroxy-2-propenoic acid] (8u) and 2-hydroxy-3-(quinoline-2-yl)propenoic acid (8v) with IC50 values of 3.0 ± 1.0 μM and 4.3 ± 1.5 μM respectively. Compound 8v is a competitive inhibitor with respect to pyruvate (Ki = 0.74 μM) and a mixed-type inhibitor with respect to ATP, indicating that it targets the unique carboxyltransferase (CT) domain of PC. Furthermore, compound 8v does not significantly inhibit human carbonic anhydrase II, matrix metalloproteinase-2, malate dehydrogenase or lactate dehydrogenase.

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

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 μM). A structure-activity relationship study of this compound further identified the 4-chloro- (IC50 = 0.18 μM) and 3-chloro- (IC50 = 0.17 μM) 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.