| Identification | Back Directory | [Name]
diethyl 2,2'-bipyridine-5,5'-dicarboxylate | [CAS]
1762-46-5 | [Synonyms]
5,5'-Dicarbethoxy-2,2'-bipyridine
5,5'-diethoxycarbonyl-2,2'-bipyridine
5,5'-Bis(ethoxycarbonyl)-2,2'-bipyridine
diethyl 2,2'-bipyridine-5,5'-dicarboxylate
5,5'-diethyl [2,2'-bipyridine]-5,5'-dicarboxylate
[2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester
[2,2′-Bipyridine]-5,5′-dicarboxylic acid, diethyl ester
2,2'-Bipyridine]-5,5'-dicarboxylic acid, 5,5'-diethyl ester
ethyl 6-(5-ethoxycarbonylpyridin-2-yl)pyridine-3-carboxylate | [Molecular Formula]
C16H16N2O4 | [MDL Number]
MFCD11110569 | [MOL File]
1762-46-5.mol | [Molecular Weight]
300.309 |
| Chemical Properties | Back Directory | [Melting point ]
145-147 °C | [Boiling point ]
428.9±45.0 °C(Predicted) | [density ]
1.201±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
powder to crystal | [pka]
1.99±0.32(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C16H16N2O4/c1-3-21-15(19)11-5-7-13(17-9-11)14-8-6-12(10-18-14)16(20)22-4-2/h5-10H,3-4H2,1-2H3 | [InChIKey]
IUNBUYCOAQHBMC-UHFFFAOYSA-N | [SMILES]
C1(C2=NC=C(C(OCC)=O)C=C2)=NC=C(C(OCC)=O)C=C1 |
| Hazard Information | Back Directory | [Uses]
Diethyl bipy55'DC is an inhibitor of collagen proline 4-hydroxylases (CP4Hs) with antifibrotic and anti-metastatic activities. Diethyl bipy55'DC can inhibit CP4H activity in cultured cells at concentrations that do not cause iron deficiency[1]. | [Synthesis]
General procedure for the synthesis of diethyl [2,2'-bipyridine]-5,5'-dicarboxylate from ethanol and 2,2'-bipyridine-5,5'-dicarboxylic acid: 2,2'-bipyridine-5,5'-dicarboxylic acid (200 mg, 0.82 mmol) and anhydrous ethanol (13 mL) were added to a dry flask with stirring under an ice bath. Thionyl chloride (1.3 mL) was slowly added dropwise, followed by installation of a reflux condenser and heating to reflux. After 24 hours of reaction, the reaction mixture was cooled in an ice bath and saturated sodium carbonate solution (20 mL) was added dropwise to quench the reaction. The aqueous phase was extracted with dichloromethane (4 x 20 mL), the organic phases were combined and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 1:1 dichloromethane/hexane solvent mixture of 3% acetone) to afford diethyl [2,2'-bipyridyl]-5,5'-dicarboxylate (190 mg, 77% yield) as a white solid.1H NMR (500 MHz, CDCl3) δ 9.32 (dd, J = 0.5, 2.0 Hz, 1H), 8.59 (dd, J = 0.5, 8.5 Hz, 1H), 8.46 (dd, J = 2.0, 8.5 Hz, 1H), 4.47 (q, J = 7.5 Hz, 2H), 1.46 (t, J = 7.5 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 165.2, 158.3, 150.6, 138.1, 126.6, 121.3, 61.6, 14.3; HRMS (ESI) m/z 301.1193 [C16H17N2O4 (M + H)+ calculated value 301.1183]. | [References]
[1] Vasta J D, et al. Selective inhibition of collagen prolyl 4-hydroxylase in human cells[J]. ACS chemical biology, 2016, 11(1): 193-199. DOI:10.1021/acschembio.5b00749 |
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