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

Product Name
ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate
CAS No.
4450-98-0
Chemical Name
ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate
Synonyms
1-Ebpc;CP-10668;Nsc 229530;EBPC, 10 mM in DMSO;EBPC, Aldose reductase inhibitor;Aldose Reductase,inhibit,EBPC,Inhibitor;1-Benzyl-4-bydroxy-5-oxo-3-pyrroline-3-carboxylic Acid Ethyl Ester;1-Benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester;2,5-Dihydro-4-hydroxy-5-oxo-1-(phenylMethyl)-1H-pyrrole-3-carboxylic Acid Ethyl Ester;1H-Pyrrole-3-carboxylic acid, 2,5-dihydro-4-hydroxy-5-oxo-1-(phenylmethyl)-, ethyl ester
CBNumber
CB51373216
Molecular Formula
C14H15NO4
Formula Weight
261.27
MOL File
4450-98-0.mol
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ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate Property

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
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Safety

Hazard Codes 
Xn
Risk Statements 
22-41
Safety Statements 
26
WGK Germany 
3
HazardClass 
IRRITANT
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PZ0140
Product name
EBPC
Purity
≥98% (HPLC)
Packaging
5mg
Price
$105
Updated
2024/03/01
Sigma-Aldrich
Product number
PZ0140
Product name
EBPC
Purity
≥98% (HPLC)
Packaging
25mg
Price
$505
Updated
2024/03/01
Cayman Chemical
Product number
14183
Product name
EBPC
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
14183
Product name
EBPC
Purity
≥98%
Packaging
5mg
Price
$93
Updated
2024/03/01
Cayman Chemical
Product number
14183
Product name
EBPC
Purity
≥98%
Packaging
10mg
Price
$139
Updated
2024/03/01
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ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate Chemical Properties,Usage,Production

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 PGF2α 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 F2α (PGF2α) 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 Preparation Products And Raw materials

Raw materials

Preparation Products

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

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4450-98-0, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylateRelated Search:

1-BENZYL-1,5-DIHYDRO-PYRROL-2-ONE Ethyl 3-(benzylamino)propanoate 1-Benzyl-2,5-dihydro-1H-pyrrole 1-(4-Methoxybenzyl)-3-hydroxy-4-ethoxycarbonyl-5-(3-pyridyl)-3-pyrrolin-2-one ETHYL 3-(N-BENZYL-N-METHYLAMINO)PROPANOATE 1-BENZYL-2,5-DIHYDRO-1H-PYRROLE-3-CARBOXYLIC ACID METHYL ESTER ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate

  • 1-Ebpc
  • 1H-Pyrrole-3-carboxylic acid, 2,5-dihydro-4-hydroxy-5-oxo-1-(phenylmethyl)-, ethyl ester
  • Nsc 229530
  • 1-Benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester
  • 1-Benzyl-4-bydroxy-5-oxo-3-pyrroline-3-carboxylic Acid Ethyl Ester
  • 2,5-Dihydro-4-hydroxy-5-oxo-1-(phenylMethyl)-1H-pyrrole-3-carboxylic Acid Ethyl Ester
  • CP-10668
  • Aldose Reductase,inhibit,EBPC,Inhibitor
  • EBPC, Aldose reductase inhibitor
  • EBPC, 10 mM in DMSO
  • 4450-98-0
  • Aromatics
  • Heterocycles
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pfizer Compounds
  • Pharmaceuticals