Novel antitumor compounds
A compound, selected technology, applied in the field of disease and tumor-related diseases, can solve the problem of no curative effect, etc.
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Embodiment 1
[0067]
[0068] Take compound 22 methyl vanillate (73g, 0.4mol) and 1-bromo-3-chloropropane (94g, 0.6mol) mixed into a 1L three-necked round bottom flask, measure 500ml of N,N-methylformamide ( DMF) was stirred and dissolved, and 80g potassium carbonate was added with heating and stirring at 40°C. The reaction progress was detected by TLC (petroleum ether: ethyl acetate=2:1, UV color development). The reaction was basically completed in 4 to 5 hours to obtain the reaction solution of compound 23. It can be used directly in the next reaction.
[0069] Take 30g potassium carbonate, 20g potassium iodide and 70g morpholine directly into the reaction solution of compound 23, heat and stir overnight at 75°C, TLC detection (petroleum ether: ethyl acetate=2:1, UV color), the raw materials are basically reacted and filtered To remove insoluble matter, the filter cake was washed with dichloromethane, the filtrate was concentrated to remove most of DMF, diluted with about 800ml of water, ex...
Embodiment 7
[0079]
[0080] Weigh 0.2g of compound 30 and 0.23g of compound 35 and mix them with about 50mL of absolute ethanol. Add 0.07g of triethylamine, 0.02g of KI at 80°C and heat and stir, react for 72h, monitor by TCL (dichloromethane: methanol: ammonia = 10: 1:0.1) To the end of the reaction, 0.09 g of compound 36 was purified by column chromatography.
[0081] MSm / z(ESI): 638[M+H] +1 ; H-NMR(500MHz, deuterated DMSO: δ:8.45(d.2H), 8.26(m.1H), 7.92(m.1H), 7.38(m.2H) 4.62(s.2H), 4.21(t .2H), 4.01(s.3H), 3.61~3.70(m.4H), 3.58(m.2H), 2.83(t.2H), 2.46~2.48(t.4H), 1.96(m.2H).
Embodiment 8
[0083]
[0084] Weigh 2.7g of compound 30 and 4g of anhydrous piperazine and mix them with about 50mL of absolute ethanol. Add 1g of triethylamine, 0.2g of potassium iodide and heat and stir at 80°C, react for 48h, and monitor by TCL (dichloromethane: methanol: ammonia = 10:1:0.1) to the end of the reaction, then concentrate to remove the ethanol, add 100mL water, extract with 50mL*3 dichloromethane, combine the organic phases, wash the organic phase with 100mL*2 saturated ammonium chloride solution and then use 100mL*2 It was washed twice with water, dried over anhydrous sodium sulfate, and concentrated to obtain 1.5 g of compound 37.
[0085] MSm / z(ESI): 464;
[0086] 1 H-NMR (500MHz, deuterated DMSO: δ: 8.45(d.2H), 8.26(m.1H), 7.92(m.1H), 7.38(m.2H), 4.62(s.2H), 4.21(t .2H), 4.01(s.3H), 3.61(t.2H), 3.29(t.2H), 2.83(t.2H), 2.46~2.48(t.4H).
[0087] Compound 38, compound 39, compound 40, compound 42, compound 43, and compound 44 have structural units similar to compound 37 or comp...
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