An acylated derivative of resiquimod, its preparation method and application
A technology for resiquimod and derivatives, which is applied in the field of anti-melanoma acylated derivatives of resiquimod and its preparation, and achieves the effects of strong selectivity, good clinical application value and good activity
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Embodiment 1
[0028] This embodiment provides an acylated derivative (B) of Resiquimod, the structure is as follows:
[0029]
[0030] The acylated derivative of the Resiquimod is prepared by the following method, the method comprising the steps of:
[0031] 1) Under ice-bath conditions, dissolve 47.2mg (0.15mMol, mw=314) resiquimod in 10ml of chloroform, add 51mg of triethylamine and 2mg of 4-dimethylaminopyridine to it, and then slowly drop Acetyl chloride in chloroform to obtain a mixed solution;
[0032] Wherein, in the chloroform solution of described acetyl chloride, 40mg acetyl chloride is dissolved in 1ml chloroform;
[0033] 2) Stir the mixture at a temperature of 25° C. until new spots appear on the TLC spot plate during TLC detection, and then add ice water to quench the reaction;
[0034] 3) In the reaction liquid of quenching reaction, adopt 10ml ethyl acetate to extract reaction liquid 3 times respectively, after liquid separation, take organic phase; After adopting anhyd...
Embodiment 2
[0038] Oral squamous cell carcinoma cells SCC-15 and human tongue carcinoma cell carcinoma cells CAL-27 were subjected to RPMI containing 10% fetal bovine serum, 1 million units of penicillin and 800,000 units of streptomycin at 37°C, 5% CO2 and saturated humidity. Cultured in 1640 complete culture medium, subcultured (frozen storage if necessary). Take two lines of oral squamous cell carcinoma SCC-15 and human tongue squamous cell CAL-27 in the logarithmic growth phase, digest with trypsin, collect the suspension, centrifuge (1000r, 4min), discard the supernatant, add the culture medium and count the cells , diluted to a concentration of 5×104 cells / ml, added to a 96-well plate, 100ul per well.
[0039] After cultivating overnight, the original culture solution was removed, and Resiquimod and Resiquimod acylated derivative B (the Resiquimod acylated derivative made in Example 1) were added to the experimental group respectively. The final concentration was 200ug / ml, 100ug / ml,...
Embodiment 3
[0047]Human melanoma cells A875 and malignant melanoma cells WM 451Lu were fully cultured in RPMI 1640 containing 10% fetal bovine serum, 1 million units of penicillin and 800,000 units of streptomycin at 37°C, 5% CO2 and saturated humidity. Cultivate and subculture in liquid (frozen storage if necessary). Take two strains of human melanoma cells A875 and malignant melanoma cells WM451Lu in the logarithmic growth phase, digest with trypsin, collect the suspension, centrifuge (1000r, 4min), discard the supernatant, add the culture medium and count the cells, dilute to a concentration of 5×104 cells / ml, add to 96-well plate, 100ul per well.
[0048] After culturing overnight, remove the original culture medium, and add Resiquimod and Resiquimod acylated derivative B culture medium with final concentrations of 200ug / ml, 100ug / ml, 50ug / ml, 25ug / ml, and 10ug / ml to the experimental group respectively, and the negative control group Add complete medium. After acting for 48 hours, r...
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