Low-oxygen activated joint chloroethane nitrourea compound and preparation method and application
A compound and composition technology, applied in the field of pharmacy, can solve the problems of non-targeting, increased toxicity and side effects of chemotherapy drugs, and enhanced damage to normal cells, etc.
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[0061] Example 1: N-(2-chloroethyl)-N’-3-(O 6 -Benzyl-N 2 -(((4-nitrobenzyl)oxy)carbonyl)9-guaninyl)ethyl-N-nitrosourea (compound 1)
[0062] 1)N9-Bromoethyl-O 6 -Synthesis of benzylguanine
[0063] Weigh O 6 -Benzylguanine (0.96g, 4mmol), anhydrous potassium carbonate (1.66g, 12mmol) were added to a three-necked flask, 100mL acetone was added, the temperature was slowly raised to 50℃, and 1,2-dibromoethane (1.4 mL, 16mmol), continue to react for 60h after the completion of dripping, filter the reaction solution, collect the filtrate, and then spin dry the solvent under reduced pressure at 40°C, and then separate and purify by silica gel column chromatography. The eluent is petroleum ether and ethyl acetate. Gradient elution, the volume ratio of petroleum ether / ethyl acetate gradually increased from 1:2 to 1:4, and dried under vacuum at 40°C to obtain white solid N9-bromoethyl-O 6 -Benzylguanine (1.11g, 3.2mmol), yield 80%.
[0064] UVλ: 250,283nm. IR(KBr tablet)v / cm -1 :3468.6(N-(...
Example Embodiment
[0080] Example 2: N-(2-chloroethyl)-N’-3-(O 6 -Benzyl-N 2 -(((4-nitrobenzyl)oxy)carbonyl)9-guaninyl)propyl-N-nitrosourea (compound 2) synthesis
[0081] 1)N9-Bromopropyl-O 6 -Synthesis of benzylguanine
[0082] Weigh O 6 -Benzylguanine (1.44g, 6mmol), anhydrous potassium carbonate (3.32g, 24mmol) were added to a three-necked flask, 150mL acetone was added, the temperature was slowly raised to 55℃, and 1,3 dibromopropane (3.03mL, 30mmol), continue to react for 65h after dripping, filter the reaction solution, collect the filtrate, and distill under reduced pressure at 40°C to remove the solvent, and then separate and purify by silica gel column chromatography. The eluent is petroleum ether and ethyl acetate, and gradient elution is adopted. , The volume ratio of petroleum ether / ethyl acetate gradually increased from 1:2 to 1:4, vacuum dried at 40°C to obtain white solid N9-bromopropyl-O 6 -Benzylguanine (1.59g, 4.4mmol), yield 73%.
[0083] UVλ: 250,284nm. IR(KBr tablet)v / cm -1 :345...
Example Embodiment
[0099] Example 3: N-(2-chloroethyl)-N’-3-(O 6 -Benzyl-N 2 Synthesis of -(((4-nitrobenzyl)oxy)carbonyl)9-guaninyl)butyl-N-nitrosourea (compound 3)
[0100] 1)N9-Bromobutyl-O 6 -Synthesis of benzylguanine
[0101] Weigh O 6 -Benzylguanine (0.72g, 3mmol), anhydrous potassium carbonate (1.66g, 12mmol) were added to a three-necked flask, 80mL acetone was added, the temperature was slowly raised to 55℃, and 1,4 dibromobutane (1.8mL) , 15mmol), continue the reaction for 70h after the completion of dripping, filter the reaction solution, collect the filtrate, after the solvent is distilled off under reduced pressure at 40°C, it is separated and purified by silica gel column chromatography. The eluent is petroleum ether and ethyl acetate. After removing, the volume ratio of petroleum ether / ethyl acetate gradually increased from 1:2 to 1:4, and dried under vacuum at 40°C to obtain white solid N9-bromobutyl-O 6 -Benzylguanine (0.79g, 2.1mmol), yield 70%.
[0102] UVλ: 250,284nm. IR(KBr tablet...
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