Anti-tumor compound containing triazole heterocyclic structure and application thereof
An anti-tumor and compound technology, applied in the field of anti-tumor compounds containing a triazole heterocyclic structure, can solve problems such as bone loss and osteoporosis, and achieve strong anti-tumor activity and good selectivity
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Embodiment 1
[0024] Synthesis of N-[3'-(4-phenyl-[1,2,3]-triazole)-propyl]-4-morpholinyl-1,8-naphthalimide (compound 1):
[0025] (1) 2.77 g of 4-bromo-1,8 naphthalene anhydride (0.01 mol) was added to 20 ml of ethylene glycol monomethyl ether, and 2.6 ml of morpholine was added thereto. Heating, reflux, thin-plate chromatography tracking reaction, until the reaction is complete, let stand overnight, filter, and weigh 2.16 grams of solids, yield 76.5%.
[0026]
[0027] (2) Get 2 grams of the product synthesized by step (1), add it to 30 milliliters of absolute ethanol, and then add 0.69 grams of n-propanolamine (0.7 ml) thereto. Raise the temperature, reflux, follow the reaction by thin-plate chromatography until the reaction is complete, let stand, and filter to obtain 2.0 g of a yellow solid.
[0028]
[0029] (3) Take 1.5 grams of the product synthesized by step (2), add it to 15 ml of ethyl acetate, slowly drop 0.8 ml of PBr3 within 20 minutes at room temperature, raise the tem...
Embodiment 2
[0038] Synthesis of N-[3'-(4-phenyl-[1,2,3]-triazole)-propyl]-4-thiomorpholine-1,8-naphthalimide (compound 2) :
[0039] Except that the morpholine ring is replaced by thiomorpholine, other synthesis and purification methods are the same as in Example 1 to obtain the target compound 2
[0040] 1HNMR (d6-CDCl 3 , 400MHz): δ (ppm): 2.46 (m, 2H), 2.97 (t, J 1 = 4Hz,J 2 = 4.4Hz, 4H), 3.50(t, J 1 = 4.4Hz,J 2 = 4.0Hz, 4H), 4.31(t, J 1 =6.4Hz,J 2 =6.8Hz, 2H), 4.54(t, J 1 =6.8Hz,J 2 =7.2Hz, 2H), 7.22(d, J=8.0Hz, 1H), 7.32(t, J 1 =6.8Hz,J 2 =7.6Hz, 1H), 7.42(t, J 1 =7.6Hz,J 2 =7.6Hz, 2H), 7.71(t, J 1 =8.0Hz,J 2 =7.6Hz, 1H), 7.80(d, J=8.0Hz, 2H), 8.04(s, 1H), 8.36(d, J=8.4Hz, 1H), 8.51(d, J=8.0Hz, 1H), 8.59 (d, J=7.2Hz, 1H).
[0041] HR-MS (m / z): C 27 h 25 N 5 o 2 S, calculated value: 483.1729, measured value: 483.1728.
Embodiment 3
[0043] Synthesis of N-[3'-(4-phenyl-[1,2,3]-triazole)-propyl]-4-hexahydropyridine-1,8-naphthalimide (compound 3):
[0044] Except replacing the morpholine ring with hexahydropyridine, other synthesis and purification methods are the same as in Example 1 to obtain the target compound 3
[0045] 1HNMR (d6-CDCl 3 , 400MHz): δ(ppm): 1.89(m, 4H), 2.45(m, 2H), 3.24(t, J 1 = 4.0Hz,J 2 =4.4Hz, 4H), 3.73(m, 2H), 4.31(t, J 1 =6.4Hz,J 2 =6.4Hz, 2H), 4.54(t, J 1 =7.2Hz,J 2 =6.8Hz, 2H), 7.17(d, J=8.4Hz, 1H), 7.32(t, J 1 =7.2Hz,J 2 =7.2Hz, 1H), 7.42(t, J 1 =7.6Hz,J 2 =7.2Hz, 2H), 7.68(t, J 1 =8.0Hz,J 2 =7.6Hz, 1H), 7.80(d, J=8.0Hz, 2H), 8.04(s, 1H), 8.39(d, J=8.4Hz, 1H), 8.49(d, J=8.4Hz, 1H), 8.58 (d, J=7.2Hz, 1H).
[0046] HR-MS (m / z): C 28 h 27 N 5 o 2 , calculated value: 465.2165, measured value: 465.2162.
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