| Identification | Back Directory | [Name]
Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI) | [CAS]
120241-79-4 | [Synonyms]
3-TYP
CS-2754
Pyridine(3-TYP)
3-TYP;3 TYP;3TYP
3-triazol-4-yl) pyridine
3-(1H-1,2,3-triazol-4-yl)pyridine
Pyridine,3-(1H-1,2,3-triazol-5-yl)-
Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI)
3-(1H-1;2;3-TRIAZOL-4-YL) PYRIDINE;3 TYP;3TYP | [Molecular Formula]
C7H6N4 | [MDL Number]
MFCD25956467 | [MOL File]
120241-79-4.mol | [Molecular Weight]
146.15 |
| Chemical Properties | Back Directory | [Melting point ]
180-182 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7)) | [Boiling point ]
386.6±17.0 °C(Predicted) | [density ]
1.296±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMF: 10 mg/ml; DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml; DMSO: 10 mg/ml; Ethanol: 5 mg/ml | [form ]
A crystalline solid | [pka]
7.54±0.70(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
3-(1H-1,2,3-Triazol-4-yl)pyridine is a reactant used in the synthesis of 4-aryl-1H-1,2,3-triazoles which possesses more Indoleamine 2,3-dioxygenase (IDO) inhibitory potency than the most commonly used 1-methyltryptophan. | [Synthesis]
General procedure: to a solution of DMF/MeOH (9:1, 4.0 mL) containing 3-ethynylpyridine (0.20 g, 1.94 mmol, 1.0 eq.), CuI (0.02 g, 0.097 mmol, 0.05 eq.) and trimethylsilyl azide (0.38 mL, 2.91 mmol, 1.5 eq.) were added in sequence. The reaction system was heated and stirred at 100 °C for 12 h under nitrogen protection. After completion of the reaction, it was cooled to room temperature, filtered through a diatomaceous earth pad and the filter cake was washed with EtOAc. The filtrates were combined and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (eluent: PE/EtOAc = 3:7, followed by pure EtOAc) and crystallized with EtOAc to afford the target compound 3-(1H-1,2,3-triazol-4-yl)pyridine (0.18 g, 64% yield) as a white solid. Melting point: 187-192 °C. 1H NMR (300 MHz, CD3OD) δ 9.03 (s, 1H), 8.51 (d, J = 3.7 Hz, 1H), 8.29-8.27 (m, 2H), 7.54-7.50 (m, 1H); 13C NMR (75 MHz, CD3OD) δ 148.3, 146.1, 143.1, 133.9, 127.3, 124.3; MS (ESI) m/z 147 [M + H]+; IR (KBr) 3467, 3118, 1637, 1560, 1434, 1311, 1134 cm-1. Calculated elemental values (C7H6N4): C, 57.53; H, 4.14; N, 38.34. Measured values: C, 57.67; H, 4.25; N, 38.10. | [in vivo]
3-TYP (50 mg/kg, i.p.) does not significantly influence the LVEF, LVFS, infarct size, serum LDH levels, apoptosis, and oxidative stress compared with those of the Sham group. Moreover, 3-TYP has little effect on gp91phox, Nrf2, NQO 1, Bax, Bcl-2, Caspase-3, and cleaved Caspase-3 expression levels, compared with the Sham group. 3-TYP significantly decreases SIRT3 activity and increases the acetylation of SOD2 compared with that in the control group, without influencing SIRT3 expression. 3-TYP attenuates the cardioprotective effects of melatonin by decreasing the LVEF and LVFS after 24 hour of reperfusion. 3-TYP also increases the infarct size, serum LDH levels, and apoptotic ratio compared with those in the IR+Mel group[2]. | [IC 50]
SIRT3: 38 μM (IC50); Methionine Aminopeptidase 2 | [storage]
Store at -20°C | [References]
[1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 58 - 66,9 |
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