Compound containing oxazole and triazole diheterocycles, and preparation method and application method thereof
A compound and biheterocycle technology, applied in the field of compounds containing oxazole and triazole biheterocycles, can solve the problems of non-disclosure
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Embodiment 1
[0098] Prepare R by the following procedure 1 =Ph, R 2 =Ph biheterocyclic compound:
[0099] (1) Add 6mmol of phenylacetylene and 25-30mL of ultra-dry tetrahydrofuran into a 100mL reaction bottle, and then carry out vacuum treatment, N 2 For protection, put the reaction bottle into the ethanol solution at -78°C, and then continue to add 6mmol of n-butyllithium. After reacting for 1-1.5h, insert a carbon dioxide balloon (inserted into the liquid surface), and react for 3-4 hours. Replace the carbon dioxide balloon again and react overnight. Thereafter, the reaction bottle was taken out, and stirred at room temperature to room temperature, 20 mL of saturated ammonium chloride solution was added into the reaction bottle, and stirring was continued for 20-30 minutes. After the reaction, first extract with diethyl ether (2×20mL), take the aqueous phase and adjust the pH to about 3 with dilute hydrochloric acid, then use ethyl acetate (2×20mL) and spin dry under low pressure to o...
Embodiment 2-20
[0111]With reference to the specific process of Example 1, the target product (I) of Examples 2-20 can be prepared respectively through the aforementioned preparation process as shown in Table 1 below:
[0112] The target product (I) of table 1 embodiment 2-20
[0113]
[0114] Characterization by NMR and high-resolution mass spectrometry can verify that the above product has the structure shown in formula (I), and the yield of the obtained product is between 55-86%.
[0115] Taking the product of Example 9 as an example, it is a light yellow solid, and its melting point is 81.2-83.5°C as measured by a SGW X-4 digital melting point apparatus.
[0116] The NMR characterization results are:
[0117] 1 H NMR (400MHz, CDCl 3 ):δ7.56–7.52(m,1H),7.44–7.41(m,1H),7.38–7.30(m,7H),6.53(s,1H),6.14(s,1H),6.03(s,2H ),1.44(s,9H),0.97(s,9H)ppm;
[0118] 13 C NMR (100MHz, CDCl 3 ): δ163.3, 156.8, 143.5, 138.6, 135.6, 134.3, 131.9, 130.3, 130.2, 129.8, 128.8, 128.2, 127.5, 126.9, 123...
Embodiment 21
[0127] Carry out tumor inhibition test on the product:
[0128] Take MGC-803 (human gastric cancer cells), T24 (human bladder cancer cells), HepG-2 (liver cancer cells), and A549 (human non-small cell lung cancer cells) in DMEM containing 10% fetal bovine serum and 1% double antibody medium, and at a temperature of 37 °C, 5% CO 2 and 95% air CO 2 cultured in an incubator. Take the cells in the logarithmic growth phase, wash with PBS three times, digest the cells with 0.25% trypsin, and stop digesting the cells with 10% serum medium. Suspend the cells with medium containing 10% serum, and gently pipette the cells to make a single cell suspension. Through cell counting, appropriate amount of cell suspension was diluted with 10% culture medium, and inoculated into 96-well plate, 180 μL per well, and the number of cells per well was 2×10 4 -4×10 4 . The sample to be tested was added to a 96-well plate with different tumor cells, 20 μL per well, so that the final concentratio...
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