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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

Inactive Publication Date: 2015-07-08
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The existing drugs for the treatment of renal fibrosis have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain potential drugs with high efficiency and low toxicity

Method used

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  • Application of O-(1H-tetrazolyl) ethyl derivative of cleistanone in preparation of medicines for treating or preventing renal fibrosis
  • Application of O-(1H-tetrazolyl) ethyl derivative of cleistanone in preparation of medicines for treating or preventing renal fibrosis
  • Application of O-(1H-tetrazolyl) ethyl derivative of cleistanone in preparation of medicines for treating or preventing renal fibrosis

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry and specifically relates to an O-(1H-tetrazolyl) ethyl derivative of cleistanone, a preparation method and application thereof in preparation of medicines for treating or preventing renal fibrosis. The invention synthesizes a new O-(1H-tetrazolyl) ethyl derivative of cleistanone and discloses the preparation method thereof. Pharmacological experiments show that the O-(1H-tetrazolyl) ethyl derivative of cleistanone has an effect for preventing or treating the renal fibrosis and has the value of developing the medicines for preventing or treating the renal fibrosis.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to an O-(1H-tetrazolyl) ethyl derivative of Cleistanone, a preparation method and use thereof. Background technique [0002] Renal fibrosis (including renal interstitial fibrosis and glomerulosclerosis) is the main pathological basis of the final stage of renal damage caused by various reasons. The proliferation and activation of stromal cells are related to the imbalance of vasoactive substances, cytokines and extracellular matrix turnover. Renal interstitial fibrosis is almost a common pathway for all primary or secondary renal diseases to progress to end-stage renal failure. There is an urgent need to develop high-efficiency and low-toxicity anti-renal fibrosis drugs. [0003] The existing drugs for the treatment of renal fibrosis have problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P13/12C07J63/00
Inventor 吴俊华江春平黄蓉
Owner NANJING UNIV
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