ppap hemiketal compound, its preparation method and its use
A compound and hemiketal technology, applied in the field of medicinal chemistry, can solve the problems of large toxic and side effects, limited anti-tumor activity, etc., and achieve the effect of good inhibitory activity
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Embodiment 1
[0026] A preparation method of PPAP compound (compound 1, 2), comprising the following steps:
[0027] (1) 50.0 kg of dried branches and leaves of wood bamboo, pulverized, extracted 4 times through methanol 4 × 50L reflux (the extraction time used was respectively 5 hours, 3 hours, 3 hours and 2 hours), concentrated to obtain 2 kg of extract, and the obtained extract After the paste was suspended in water, it was sequentially extracted 4 times with 10L ethyl acetate, and concentrated to obtain 500 g of ethyl acetate;
[0028] (2) 500 g of the ethyl acetate part was roughly separated by 200-300 mesh silica gel chromatography column, separated by RP-C18 reverse phase column gradient (methanol / water, 2:8→10:0), silica gel column chromatography (chloroform / ethyl acetate) separation and purification to obtain 50 g of compound 1 (structural formula II).
[0029] Compound 1 was identified by NMR spectrum. The NMR data of Compound 1 are shown in Table 2.
[0030]
[0031] (3) A...
Embodiment 2
[0035] A preparation method of PPAP compound (compound 3), comprising the following steps:
[0036] (1) method obtains compound 2 with embodiment 1;
[0037] (2) Add compound 2 (20mg), 3ml dichloromethane and 3.0 equivalents of triethylamine to the reactor in turn, then cool down to 0°C, add 2.5 equivalents of acetyl chloride, then let it slowly warm up to room temperature 25°C for reaction 1 After 1 hour, 10 ml of water was added to quench the reaction, extracted with 20 ml of ethyl acetate, and the ethyl acetate was recovered to obtain a yellow oily crude product. After separation by silica gel column chromatography, compound 3 (structural formula IV) was obtained with a yield of 22%.
[0038]
[0039] Compound 3 was identified by NMR and ESI-MS spectra. ESI-MS: m / z 727[M+Na] + , HRMS (ESI): m / zcalcd.for C 56 h 89 N 2 o 6 [M+Na] + 727.3822found 727.3818. The NMR data of compound 3 are shown in Table 2.
Embodiment 3
[0041] A preparation method of PPAP compounds (compound 4), comprising the following steps:
[0042] (1) method obtains compound 2 with embodiment 1;
[0043](2) Add 50mg of compound 2, 3ml of dichloromethane and 1.5 equivalents of triethylamine to the reactor in sequence, then cool down to 0°C, add 1.2 equivalents of propionyl chloride, then let it slowly warm up to room temperature 25°C, and react 2 After 1 hour, 5 ml of water was added to quench the reaction, extracted three times with 10 ml of ethyl acetate, and the ethyl acetate was recovered to obtain a yellow oily crude product. After separation by silica gel column chromatography, the target compound 4 (structural formula V) was obtained with a yield of 30%.
[0044] Compound 4 was identified by NMR and ESI-MS spectra. Compound 4: ESI-MS: m / z 699 [M+Na] + , HRMS (ESI): m / z calcd.for C 41 h 56 NaO 8 [M+Na] + 699.3862found 699.3873. The NMR data of compound 4 are shown in Table 2.
[0045]
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