Oleanane derivative with carbonyl and oxygen substituent at C ring and use thereof
A technology for oleanane and derivatives, which is applied in the field of polyoxidatively substituted pentacyclic triterpenoid derivatives and their preparation, can solve the problem of high incidence of adverse reactions of non-steroidal anti-inflammatory drugs, liver failure, and aggravation of digestion. canal ulcers
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preparation example 1
[0030] Preparation Example 1: Preparation of Compound Ii
[0031] The compound 3-methylsulfonyloxy-oleanane-28-acid-12-ene (1.0mmol) was dissolved in 5 ml of DMAC (N,N'-dimethylacetamide), and lithium carbonate ( 2.0 mmol). The reaction mixture was heated to reflux for half an hour. After cooling, excess lithium carbonate was filtered off, the filtrate was added to 10 ml of water, extracted with ether, and the organic phase was washed with water until neutral. Dry over anhydrous sodium sulfate. Silica gel column chromatography (eluent: petroleum ether / ethyl acetate: 8 / 1) gave oleanane-28-acid-2,12-diene as a white solid with a yield of 82%.
[0032] In 20 ml of acetic acid (containing 5% acetic anhydride), the compound oleanane-28-acid-2,12-diene (0.82 mmol) and chromium trioxide (4.92 mmol) were added, and stirred overnight at room temperature. The reaction compound was poured into 20 ml of water, and extracted with chloroform. The organic phase was washed with saturated...
preparation example 2~ preparation example 22
[0034] According to the method of Preparation Example 1, the compounds of Preparation Example 2 to Preparation Example 22 shown below were prepared:
preparation example 2
[0035] Preparation Example 2: Preparation of oleanane-28-acid-2,11,13(18)-triene (Ia), C 30 h 44 O 2 , MS: ESIm / e436 (M + ); Rf (petroleum ether / chloroform / methanol: 4 / 4 / 0.6): 0.63, 1 HNMR (400MHz, CDCl 3 )δ: 2.51(brd, 1H, J=14.2Hz, H-19), 5.31-5.43(m, 3H, H-2, H-3, H-12), 6.35(d, 1H, J=10.4Hz , H-11).
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