ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate Chemical Properties

Melting point:

135-136 °C

Boiling point:

479.8±45.0 °C(Predicted)

Density 

1.340±0.06 g/cm3(Predicted)

storage temp. 

room temp

solubility 

DMSO: ≥10mg/mL

form 

white powder

pka

4.50±1.00(Predicted)

color 

white

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate Usage And Synthesis

Description

The human aldose reductase AKR1B1 is considered the rate limiting enzyme of the polyol pathway responsible for the conversion of glucose into sorbitol. It also acts as a highly efficient PGF_2α synthase in response to interleukin-1β. Increased aldose reductase expression has been associated with complications of diabetes and may contribute to reduced efficacy of certain chemotherapeutic drugs. EBPC is a potent, selective inhibitor of aldose reductase with an IC₅₀ value of 47 nM in vitro. Through its regulation of glucose metabolism, EBPC has been used to improve the cytotoxic effects of the anticancer agents doxorubicin and cisplatin in HeLa cervical carcinoma cells. EBPC also inhibits prostaglandin F_2α (PGF_2α) and PGE₂ production in human endometrial cells with an EC₅₀ value of 10 μM.

Uses

A highly specific aldose reductase inhibitor that has been shown to enhance HeLa cell sensitivity to chemotherapeutic drugs.

Definition

ChEBI: Ethyl 1-benzyl-3-hydroxy- 2-oxo[5H]pyrrole-4-carboxylate is a pyrroline and a carboxylic acid.

References

[1] B. L. MYLARI T W S T A Beyer. A Highly Specific Aldose Reductase Inhibitor, Ethyl 1-Benzyl-3-hydroxy- 2(5H)-oxopyrrole-4-carboxylate, and Its Congeners.[J]. ChemInform, 1991, 90 1. DOI: 10.1002/chin.199127155
[2] EUN KYOUNG LEE  Paul S  William T Regenold. Inhibition of aldose reductase enhances HeLa cell sensitivity to chemotherapeutic drugs and involves activation of extracellular signal-regulated kinases.[J]. Anti-Cancer Drugs, 2002, 13 8: 859-868. DOI: 10.1097/00001813-200209000-00012
[3] EVA BRESSON. The Prostaglandin F Synthase Activity of the Human Aldose Reductase AKR1B1 Brings New Lenses to Look at Pathologic Conditions.[J]. Frontiers in Pharmacology, 2012, 3: 98. DOI: 10.3389/fphar.2012.00098

ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate(4450-98-0)Related Product Information

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