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 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 Preparation Products And Raw materials

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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