Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate
Grundinformationen
- CAS
4450-98-0- Standard-SMILES
CCOC(=O)C1=C(O)C(=O)N(Cc2ccccc2)C1- InChIKey
IGYRPDIWSYGHMY-UHFFFAOYSA-N- Summenformel
- C14H15NO4
- Durchschnittliche Molmasse
- 261,27 g/mol
- Monoisotopische Masse
- 261,10010796
Überblick
Ethyl 1-benzyl-3-hydroxy- 2-oxo[5H]pyrrole-4-carboxylate is a pyrroline and a carboxylic acid.
Namen und Bezeichner
- Bevorzugter Name
- Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate
- IUPAC
- ethyl 1-benzyl-4-hydroxy-5-oxo-2H-pyrrole-3-carboxylate
- Englischer Name
- ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate
- Summenformel
- C14H15NO4
- Molmasse
- 261.27
Namen und Synonyme
4450-98-0Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate1-EbpcMW8LQ9P85CDTXSID50196205NSC-2295301H-Pyrrole-3-carboxylic acid, 2,5-dihydro-4-hydroxy-5-oxo-1-(phenylmethyl)-, ethyl esterRefChem:138475DTXCID20118696EBPC1-Benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl esterMFCD00179167
Weitere Namen anzeigen
CP-10668Nsc 229530EBPC, 10 mM in DMSOEBPC, Aldose reductase inhibitorAldose Reductase,inhibit,EBPC,Inhibitor1-Benzyl-4-bydroxy-5-oxo-3-pyrroline-3-carboxylic Acid Ethyl Ester2,5-Dihydro-4-hydroxy-5-oxo-1-(phenylMethyl)-1H-pyrrole-3-carboxylic Acid Ethyl Ester
ethyl 1-benzyl-4-hydroxy-5-oxo-2H-pyrrole-3-carboxylateethyl 1-benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylateNSC229530ETHYL 1-BENZYL-3-HYDROXY- 2-OXO[5H]PYRROLE-4-CARBOXYLATENSC 229530;NSC-229530;NSC229530SMR000567214Spectrum_001772SpecPlus_000694
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,7
- Polarare Oberfläche (TPSA)
- 66,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 396
Experimentelle und physikochemische Eigenschaften
Solubility>39.2 [ug/mL] (The mean of the results at pH 7.4)
Physikochemische Eigenschaften
- Schmelzpunkt
- 135 · 135-136 °C
- Siedepunkt
- 479.8 · 479.8±45.0 °C(Predicted)
- Dichte
- 1.34 · 1.340±0.06 g/cm3(Predicted)
- storage temp.
- room temp
- Löslichkeit
- 10 mg/mL · DMSO: ≥10mg/mL
- Aggregatzustand
- white powder
- pka
- 4.5 · 4.50±1.00(Predicted)
- Farbe
- white
- InChI
- 1S/C14H15NO4/c1-2-19-14(18)11-9-15(13(17)12(11)16)8-10-6-4-3-5-7-10/h3-7,16H,2,8-9H2,1H3
- InChIKey
- IGYRPDIWSYGHMY-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C1=C(O)C(=O)N(Cc2ccccc2)C1
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- 3
- risk_code
- 22-41
- hazard_code
- Xn
- safety_code
- 26
- hazard_class
- IRRITANT
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1
Chemie und Industrie
Anwendungen
BeschreibungThe 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.
VerwendenA highly specific aldose reductase inhibitor that has been shown to enhance HeLa cell sensitivity to chemotherapeutic drugs.
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