Sulfur-bearing uridine anticancer drug, intermediate and synthesis method
A technology of anticancer drugs and synthetic methods, which is applied in the direction of drug combinations, chemical instruments and methods, and antineoplastic drugs. The effect of easy access to raw materials
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[0056] Example 1: A 4-thio-5-(2-furyl)uridine, its intermediates and synthesis methods, including the following steps:
[0057] (1) Synthesis of 5-iodouridine
[0058]
[0059] Dissolve uridine (0.55 g, 2 mmol) in 10 mL of 0.3mol / L dilute nitric acid, add elemental iodine (0.504 g, 1.98 mmol), and heat at reflux for 100 min until the raw materials are completely reacted (tracking monitoring by thin layer chromatography) . After the reaction was stopped, it was filtered hot to remove excess iodine. The filtrate was extracted with petroleum ether until the solution was clear. Placed at 4°C, a large number of colorless needle-like crystals of 5-iodouridine were obtained. After drying, it was weighed to obtain 0.63 g. Yield 75%. m. p. 205-207℃, (literature value m. p. 208-210℃);
[0060] 1 H NMR (400 MHz, DMSO-d 6 ) (ppm): 11.71(br s,1H, NH), 8.50(s, 1H, 6-H), 5.74(d, 1H, J = 4.0 Hz, 1'-H), 5.10, 5.29, 5.44(d , t, d, 1H, 1H, and 1H, OH), 4.05 (dd, 1H, J = 4.0 Hz, 8.0Hz, 2'-H), 4.00 ...
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[0076] Example 2: A 4-thio-5-(2-thienyl)uridine and its intermediates and synthesis method, including the following steps:
[0077] (1) Synthesis of 5-iodouridine
[0078]
[0079] Dissolve uridine (0.55 g, 2 mmol) in 10 mL of 0.3mol / L dilute nitric acid, add elemental iodine (0.504 g, 1.98 mmol), and heat at reflux for 100 min until the raw materials are completely reacted (tracking monitoring by thin layer chromatography) . After the reaction was stopped, it was filtered hot to remove excess iodine. The filtrate was extracted with petroleum ether until the solution was clear, and placed at 4°C to obtain a large amount of colorless needle-like crystals of 5-iodouridine. After drying, it was weighed to obtain 0.63 g. Yield 75%. m. p. 205-207℃, (literature value m. p. 208-210℃);
[0080] 1 H NMR (400 MHz, DMSO-d 6 ) (ppm): 11.71(br s,1H, NH), 8.50(s, 1H, 6-H), 5.74(d, 1H, J = 4.0 Hz, 1'-H), 5.10, 5.29, 5.44(d , t, d, 1H, 1H, and 1H, OH), 4.05 (dd, 1H, J = 4.0 Hz, 8.0 Hz, 2'-H), 4...
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[0097] Example 3: A 4-thio-5-(2-furyl)-2'-deoxyuridine, its intermediates and synthesis methods, including the following steps:
[0098] (1) Synthesis of 3',5'-O-dioxoacetyl-5-iodo-2'-deoxyuridine
[0099]
[0100] In a 100 mL three-necked flask, add 5-iodo-2'-deoxyuridine (1.0 g, 2.82 mmol) and anhydrous pyridine (15 mL, 183 mmol). After it is fully dissolved, add purified acetic anhydride (3.0 mL, 32 mmol), react in an ice bath for 16 h, remove the solvent under reduced pressure, then add 10 mL each of dichloromethane and benzene, remove the solvent again under reduced pressure, and add dichloromethane (20 mL), remove the solvent under reduced pressure. The crude product was dissolved in dichloromethane (250 mL), and then saturated NaHCO was added 3 (80 mL), extracted three times with dichloromethane. Anhydrous NaSO for organic phase 4 Dry, filter, and remove the solvent from the filtrate under reduced pressure. 1.5 mL of 95% ethanol was added, and then the mixture was placed...
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