Cembratriene-4-ol-6-carboxylate and its preparation method and application
A technology of cembratriene and carboxylate, applied in the direction of carboxylate preparation, carboxylic acid amide preparation, organic chemical methods, etc., can solve the problem of no anti-tumor activity, etc., achieve rich content, easy to obtain, and simple synthesis method Effect
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Embodiment 1
[0028] Synthesis of compound 1
[0029]
[0030] Compounds 1a-1c were synthesized using the following method
[0031] Weigh α-cembratriene-4,6-diol (95mg, 0.310mmol) into a flask, place it on a magnetic heating stirrer, add 0.5ml of pyridine dropwise to dissolve, and then slowly add 0.5ml during stirring ml of acid anhydride, reacted at room temperature for 12 hours, and monitored by TLC during the reaction. After the reaction, the saturated NaHCO 3 Wash to adjust the pH value to be close to 7, then wash and extract with dichloromethane 50ml×3, combine the organic phases, wash with saturated sodium chloride 50ml×2, pure water 50ml×2, and use anhydrous sodium sulfate for the organic phase Let dry overnight. Suction filter and spin dry. The product was subjected to silica gel column chromatography, 200-300 mesh silica gel, eluted with eluent (petroleum ether / ethyl acetate=10:1), 10 ml of each fraction, monitored by TLC, and the fractions containing the target compound wer...
Embodiment 2
[0035] Compound 1d-1r was synthesized using the following method
[0036] Add EDC (59mg, 0.31mmol) in 10ml of dry dichloromethane solution in the round-bottomed flask, stir under ice-bath conditions, acid (40mg, 0.29mmol) is slowly added dropwise in the round-bottomed flask, then in the ice-bath Slowly add DMAP (2.6mg, 0.02mmol) under stirring condition, after activation in ice bath for 2h, add α-cembratriene-4,6-diol (60mg, 0.2mmol), react for 30min, then place at room temperature The reaction was carried out for 4 h and monitored by TLC during the reaction. After the reaction was completed, saturated NaHCO was used successively 3 , dichloromethane 50ml×3, sodium chloride 50ml×2, pure water 50ml×2 for washing and extraction, and combine the organic phases. Add about 30 g of anhydrous sodium sulfate to the organic phase, seal it and put it in the refrigerator, dry it overnight, filter and spin dry with suction. The product was subjected to silica gel column chromatography, ...
Embodiment 3
[0042] For in vitro anti-tumor screening, SMMC-772 was used as liver cancer cell line, A-549 lung cancer cell line, MCF-7 breast cancer cell line, and SW480 colon cancer cell line for testing; the detection method was MTT method.
[0043]MTT method: use 10% fetal calf serum culture medium (DMEM or RMPI1640) to prepare a single cell suspension, inoculate 10000-20000 cells per well into a 96-well plate with a volume of 100 μL per well, and inoculate adherent cells 12 hours in advance nourish. Add the compound solution to be tested (fixed concentration of 40 μM for primary screening, at which concentration the compound that inhibits tumor cell growth near 50% is set to enter gradient rescreening at 5 concentrations), the final volume of each well is 200 μL, and 3 complexes are set for each treatment. hole. After culturing at 37°C for 48 hours, add 20 μL of MTT solution to each well. Continue to incubate for 4 hours, terminate the culture, carefully discard 100 μL of the culture...
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