Inhibitor with pyrimido-triazole-tetrazole-thione LSD1 (lysine specific demethylase 1), preparation method of inhibitor and application
A technology of mercaptotetrazolium and triazole, applied to medical preparations containing active ingredients, pharmaceutical formulas, organic active ingredients, etc.
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Embodiment 1
[0053] Compound 8 of Example 1, R 1 =Propyl-S-, R 3 = Preparation of Me-
[0054] (1) Compound 2 (R 1 = Preparation of Propyl-S-)
[0055] Barbituric acid (3g, 1eq) and triethylamine (2.9ml, 1eq) were added to 30ml of methanol, under reflux, bromopropane (1.8ml, 1eq) was slowly added dropwise, and reflux was continued for 1 hour after the addition , cooled, and suction filtered to obtain 3.7g of pink solid compound 2b with a yield of 97%.
[0056] (2) Compound 3 (R 1 = Preparation of Propyl-S-)
[0057] Under ice bath, carefully dissolve 3ml of fuming nitric acid in 6ml of acetic acid, then add 2.9g of compound 2b in batches, after the addition, continue to stir for 2 hours, then add the reaction solution to 18ml of ice water, filter with suction, After washing with water, a dark red powder compound 3b was obtained with a yield of 77.5%.
[0058] (3) Compound 4 (R 1 = Preparation of Propyl-S-)
[0059] Compound 3b (12.4g, 1eq) was dissolved in 50ml of phosphorus oxy...
Embodiment 2
[0068] Example 2 Compound 9, R 1 =Propyl-S-, R 3 = Preparation of Me-
[0069] Furfurylamine replaces ethanolamine, adopts the same method of embodiment 7 to prepare 9. 1 HNMR (400MHz, CDCl 3 ,ppm):δ7.36-7.37(d,J=1.2Hz,1H),6.50-6.51(d,J=3.2Hz,1H),6.35-6.36(m,1H),5.74(s,2H), 4.13(s,3H),2.91-2.94(t,J=7.4Hz,2H),1.62-1.67(m,2H),0.99-1.03(t,J=7.4Hz,3H). 13 CNMR (100MHz, CDCl 3 , ppm): δ171.46, 158.02, 149.18, 146.81, 145.05, 143.51, 131.09, 110.81, 110.48, 43.43, 34.82, 33.54, 22.14, 13.37. Yield 66%.
Embodiment 3
[0070] Example 3 Compound 10, R 1 =Propyl-S-, R 3 = Preparation of Me-
[0071] Thiphenethylamine replaces ethanolamine, adopts the same method of embodiment 7 to prepare 10. 1 HNMR (400MHz, CDCl 3 ,ppm): δ7.13-7.14(m,1H),6.87-6.89(m,1H),6.75-6.76(d,J=3.2Hz,1H),4.83-4.86(t,J=7.2Hz,2H ),4.14(s,3H),3.55-3.59(t,J=7.2Hz,2H),2.87-2.91(t,J=7.2Hz,2H),1.58-1.65(m,2H),0.99-1.02( t,J=7.2Hz,3H). 13 CNMR (100MHz, CDCl 3 , ppm): δ171.18, 157.92, 149.45, 145.08, 138.36, 131.06, 127.16, 126.08, 124.68, 48.37, 34.83, 33.50, 29.59, 22.17, 13.40. Yield 72%.
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