Polyethyleneglycol modified scutellarin compound and preparation thereof
A technology of scutellarin and polyethylene glycol, which is applied in the field of PEG-modified prodrugs and its preparation, can solve the problems of research, low solubility, no pharmacokinetics and pharmacodynamics, etc., to improve water solubility, The effect of enhancing biological activity
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[0110] Example 1: Synthesis of scutellarin-polyethylene glycol (400) monomethyl ether-6"-ester (compound I-400)
[0111]
[0112] Add scutellarin 9.24g, mPEG(400)12g, HOBt4.05g, DCC6.18g (molar ratio 1:1.5:1.5:1.5) into 80mL DMF to dissolve, pass nitrogen to protect the reaction system, and heat to 40℃ Reaction for 6 hours, TLC detects the end of the reaction (CH 2 Cl 2 :CH 3 OH:HCOOH=10:1:0.2). After the reaction is complete, add water to terminate the reaction, filter out part of the solid, and concentrate the filtrate under reduced pressure to distill off DMF and water. The crude product of viscous substance is subjected to CH 2 Cl 2 :CH 3 The eluent of OH:HCOOH=10:1:0.1 was separated and purified through a silica gel column three times to obtain 7.65 g of a pale yellow powdered solid with a yield of 45.3%.
[0113] 1H NMR (DMSO-d6, 300MHz): δH 6.81 (1H, S, C 3 -H), 7.00(1H, S, C 8 -H), 7.93 (2H, d, J=8.9 Hz, C 2’,6’ -H), 6.96 (2H, d, J=8.9 Hz, C 3’,5’ -H), 5.20 (1H, d, J=6.8...
Example Embodiment
[0115] Example 2: Synthesis of scutellarin-polyethylene glycol (600) monomethyl ether-6"-ester (compound I-600)
[0116] Add scutellarin 13.86g, mPEG(600)27g, HOBt6.07g, DCC9.27g (molar ratio 1:1.5:1.5:1.5) into 120mL of DMF to dissolve, protect the reaction system with nitrogen, and heat to 45℃ Reaction for 8 hours, TLC detects the end of the reaction (CH 2 Cl 2 :CH 3 OH:HCOOH=10:1:0.2). After the reaction is completed, add water to terminate the reaction, filter out part of the solid, concentrate the filtrate under reduced pressure to distill off DMF and water, and pass the crude product of viscous substance to CH 2 Cl 2 :CH 3 The eluent of OH:HCOOH=10:1:0.1 was separated and purified through a silica gel column three times to obtain 12.62 g of light yellow powdery solid, with a yield of 40.3%.
[0117] 1 H NMR (DMSO-d6, 300MHz): δH 6.81 (1H, S, C3-H), 7.00 (1H, S, C 8 -H), 7.93 (2H, d, J=8.9 Hz, C 2’,6’ -H), 6.96 (2H, d, J=8.9 Hz, C 3’,5’ -H), 5.20 (1H, d, J=6.8, C 1” -H), 4.21...
Example Embodiment
[0119] Example 3: Synthesis of scutellarin-polyethylene glycol (1000) monomethyl ether-6"-ester (compound I-1000)
[0120] Add scutellarin 9.24g, mPEG(1000)30g, HOBt4.05g, DCC6.18g (molar ratio 1:1.5:1.5:1.5) into 150mL DMF to dissolve, pass nitrogen to protect the reaction system, and heat to 50℃ Reaction for 10 hours, TLC detects the end of the reaction (CH 2 Cl 2 :CH 3 OH:HCOOH=10:1:0.2). After the reaction is complete, add water to terminate the reaction, filter out part of the solid, concentrate the filtrate under reduced pressure to distill off DMF and water, and pass the viscous crude product through CH 2 Cl 2 :CH 3 The eluent of OH:HCOOH=10:1:0.1 was separated and purified through a silica gel column three times to obtain 10.54 g of a light yellow powdered solid with a yield of 36.5%.
[0121] 1 H NMR (DMSO-d6, 300MHz): δH 6.82 (1H, S, C3-H), 7.03 (1H, S, C8-H), 7.94 (2H, d, J=8.9 Hz, C2', 6'- H), 6.95 (2H, d, J=8.9 Hz, C3', 5'-H), 5.27 (1H, d, J=6.8, C1"-H), 4.21 (1H, d, ...
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