Nitric oxide probe and preparation and application thereof
A nitric oxide and reaction technology, applied in chemical instruments and methods, phosphorus organic compounds, medical preparations containing active ingredients, etc., can solve problems such as limited value, difficult synthesis, difficult detection of metal probes and DAN in vivo
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
preparation example Construction
[0068] The preparation method of formula I compound of the present invention comprises: make formula a compound and formula b compound react, obtain formula 1 compound:
[0069]
[0070] The compound of formula 1 is then reacted with the compound of formula 3 to obtain the compound of formula I:
[0071]
[0072] Wherein, R in formula a and formula 1 is H, C1-C6 alkyl, or C1-C6 alkyl optionally substituted by one or more substituents selected from C1-C6 alkyl, C1 -C6 alkoxy, halogen and hydroxy.
[0073] The reaction of formula a and formula b can be carried out in the presence of acetate, catalyst and organic solvent. Suitable acetates include, but are not limited to, potassium acetate, sodium acetate, and the like. The catalyst can be any catalyst suitable for the reaction of formula a and formula b, exemplary catalysts include but are not limited to PdCl 2 (dppf). The organic solvent can be various organic solvents known in the art, including but not limited to N,...
Embodiment 1
[0098] Embodiment 1: the preparation of compound 1
[0099]
[0100] Compound 7-bromo-N-methyltetrahydroquinoline (710mg, 3.15mmol), pinacol diboronate (962mg, 3.78mmol) and potassium acetate (928mg, 9.47mmol) were added to a 100mL round bottom flask, Then add 15mL of N,N-dimethylformamide (DMF) and stir well. After replacing the air in the bottle with argon three times, PdCl was added 2 (dppf) (257 mg, 0.32 mmol). Under the protection of argon, it was heated to 80° C. and reacted overnight. DMF was removed with a rotary evaporator, followed by extraction with water and dichloromethane, and the dichloromethane layer was collected. Join MgSO 4 After drying, the filtrate was collected by filtration and spin-dried. After column chromatography (developing solvent is V 石油醚 :V 乙酸乙酯 =20:1), 540 mg of compound 1 was obtained, yield 62%.
[0101] 1 H NMR (400MHz, CDCl 3 )δ7.10(d, 1H, J=7.2Hz), 7.05(s, 1H), 6.98(d, 1H, J=7.2Hz), 3.23(t, 2H, J=5.2Hz), 2.95(s, 3H),2.79(t,2H,...
Embodiment 2
[0102] Embodiment 2: the preparation of compound 2
[0103]
[0104] (2-Aminoethyl)triphenylphosphine bromide (4 g, 9.93 mmol) and triethylamine (0.2 mL) were dissolved in 25 mL of anhydrous dichloromethane (DCM), and stirred at room temperature for 15 minutes. A solution of 5-amino-1-naphthalenesulfonyl chloride (2 g, 8.28 mmol) in dichloromethane was slowly added, and stirring was continued for 2-3 hours until the reaction of the starting material was complete. The reaction solution was extracted three times with water and dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, the filtrate was collected by filtration, and spin-dried to obtain 4.23g of compound 2, with a yield of 94%.
[0105] 1 H NMR (400MHz, CDCl 3 )δ8.38(d,1H,J=8.0Hz),8.28(d,1H,J=8.0Hz),8.26(d,1H,J=8.0Hz),7.88(d,1H,J=9.0Hz) ,7.70(s,1H),7.64(d,1H,J=9.0Hz),7.47(t,1H,J=9.0Hz),7.38-7.30(m,15H),4.74(s,2H),3.86- 3.79(m, 2H),3.73-3.67(m,2H). 13 C NMR (101MHz, CDCl 3 )δ147.5, 143.7...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More