Thioproninyl-met-aa, its synthesis, activity and application
A technology of tioproninyl and -met-aa, applied in the field of biomedicine, can solve problems such as inconvenient medication and incomplete brain lead removal
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Embodiment 1
[0017] Example 1 Preparation of Boc-Met-Ala-OBzl (2a)
[0018] Add 4g (16.0mmol) Boc-Met to a 250mL eggplant bottle and dissolve it with 100mL anhydrous tetrahydrofuran (THF), add 2.4g (16.8mmol) 1-hydroxybenzotriazole ( HOBt), completely dissolved. Slowly add the THF solution of 4.4g (20.8mmol) dicyclohexylcarbodiimide (DCC), after the reaction solution was activated for 30min, a large amount of dicyclohexylurea (DCU) was generated, and 4.1g (2.0 mmol) HCl·Ala-OBzl was added to the reaction solution, and the pH value was adjusted to 8-9 with N-methylmorpholine (NMM). Stir at room temperature for 12 h, monitor the progress of the reaction by TLC (dichloromethane / methanol=20:1), and the starting point disappears. DCU was removed by filtration under reduced pressure, and the solvent was removed from the filtrate under reduced pressure. Dissolve the residue with 100 mL ethyl acetate, followed by saturated NaHCO 3 Aqueous solution (30mL×3), saturated NaCl solution (30mL×3), sa...
Embodiment 2
[0019] Example 2 Preparation of HCl Met-Ala-OBzl (3a)
[0020] Add 7g (16.0mmol) Boc-Met-Ala-OBzl into a 250mL eggplant bottle, dissolve it with 20mL of anhydrous ethyl acetate, add 70mL of 4N hydrogen chloride in ethyl acetate solution under ice bath (0°C), and The reaction was stirred for 2 h, and the reaction progress was monitored by TLC. The raw material point disappeared (dichloromethane / methanol=20:1), and the reaction solution was concentrated with a water pump under reduced pressure. The residue was dissolved in anhydrous ethyl acetate, concentrated under reduced pressure, and repeated 3 times, then anhydrous ether was added to infiltrate the residue, and then concentrated under reduced pressure, repeated 3 times to obtain the title compound as a yellow oil.
Embodiment 3
[0021] Example 3 Preparation of Tioproninyl-Met-Ala-OBzl (4a)
[0022] Add 2.6g (16.0mmol) tiopronin to a 250mL eggplant bottle, dissolve it in 100mL anhydrous THF, add 2.4g (16.8mmol) HOBt in an ice bath (0°C), slowly add 4.4g (20.8mmol) ) THF solution of DCC, activate the reaction solution for 30min, a large amount of DCU is precipitated, add 7.0g (16mmol) HCl Met-Ala-OBzl to the reaction solution under ice bath condition, adjust the pH value to 8-9 with NMM. The reaction was stirred at room temperature for 8 h, and the progress of the reaction was monitored by TLC (petroleum ether / ethyl acetate=1:4), and the starting point disappeared. DCU was removed by filtration under reduced pressure, and the solvent was removed from the filtrate under reduced pressure. The residue was dissolved with 100 mL ethyl acetate, followed by saturated NaHCO 3 solution (30mL×3), saturated NaCl solution (30mL×3), saturated KHSO 4 solution (30mL×3), saturated NaCl solution (30mL×3), saturated N...
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