Application of O-(1H-tetrazolyl) ethyl derivative of cleistanone in preparation of medicines for treating or preventing renal fibrosis
A technology of ethyl derivatives and cleusenone, applied in drug combinations, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of low safety and high toxicity, and achieve good anti-renal fibrosis effect
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Embodiment 1
[0017] Example 1 Preparation of the compound Cleistanone
[0018] The preparation method of compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. (Van Trinh Thi Thanh et al., 2011. Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a New Carbon Skeleton. Volume 2011, Issue 22 , pages 4108–4111, August 2011).
[0019]
Embodiment 2
[0020] Example 2 Synthesis of O-bromoethyl derivative (II) of Cleistanone
[0021] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and to the solution was added tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25°C for 24h. After 24 h, the reaction solution was poured into ice water, immediately extracted twice with dichloromethane, and the organic phase solutions were combined. Then, the organic phase solution was washed with water and saturated brine three times in turn, dried over anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the yellow concentrated elution bands were collected to obtain compound II as a yellow solid (344 mg, 63%).
[0022] 1H NMR (500MH...
Embodiment 3
[0026] Example 3 Synthesis of O-(1H-tetrazolyl)ethyl derivative (III) of Cleistanone
[0027] Compound II (273 mg, 0.5 mmol) was dissolved in 15 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and 1H-tetrazolium (1401 mg, 20 mmol) were added thereto, and the mixture was heated Reflux for 10h. After the reaction, the reaction solution was poured into ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. Due to tautomerism, two substitution products, 1H-tetrazolyl and 2H-tetrazolyl, are formed under the reaction conditions. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), the yellow conce...
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