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Application of O-(pyrrolidin)ethyl derivatives of Cleistanone to preparation of anti-osteoporosis drug

A technology of tetrahydropyrrolyl and ethyl derivatives, which can be used in drug combinations, medical preparations containing active ingredients, bone diseases, etc., and can solve the problems of high toxicity and low safety.

Inactive Publication Date: 2014-12-10
路春芝
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The existing drugs for the treatment of osteoporosis 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-(pyrrolidin)ethyl derivatives of Cleistanone to preparation of anti-osteoporosis drug
  • Application of O-(pyrrolidin)ethyl derivatives of Cleistanone to preparation of anti-osteoporosis drug
  • Application of O-(pyrrolidin)ethyl derivatives of Cleistanone to preparation of anti-osteoporosis drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of Example 1 Compound Cleistanone

[0023] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. –4111, August 2011).

[0024]

Embodiment 2

[0025] Synthesis of O-bromoethyl derivatives (II) of cleistanone Cleistanone of embodiment 2

[0026] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and 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 24 h. After 24 hours, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed with water and saturated brine three times successively, then dried with 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 band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0027] 1H NMR ...

Embodiment 3

[0031] Example 3 Synthesis of O-(tetrahydropyrrolyl) ethyl derivatives (III) of cleistanone Cleistanone

[0032]Compound II (273 mg, 0.5 mmol) was dissolved in 20 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and pyrrolidine (1420 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 8 h. After the reaction was completed, 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 successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and 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 light yellow concentrated elution band was collected to obtain the O-(tetrahydropyrrolyl)ethyl deriv...

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry and particularly relates to O-(pyrrolidin)ethyl derivatives of Cleistanone, a preparation method of the O-(pyrrolidin)ethyl derivatives of Cleistanone and an application of the O-(pyrrolidin)ethyl derivatives of Cleistanone to preparation of an anti-osteoporosis drug. The invention discloses novel O-(pyrrolidin)ethyl derivatives of Cleistanone and a preparation method of the novel O-(pyrrolidin)ethyl derivatives of Cleistanone. Pharmacological experiments prove that the O-(pyrrolidin)ethyl derivatives of Cleistanone have an anti-osteoporosis effect and has a value of developing the anti-osteoporosis drug.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(tetrahydropyrrolyl)ethyl derivatives of cleistanone, a preparation method and uses thereof. Background technique [0002] Osteoporosis is a systemic, metabolic bone disease characterized by reduction and loss of bone mass, bone fragility and increased risk of fracture. With the aging of the population, the incidence of osteoporosis has also increased rapidly, and it has become an important disease that endangers human health and has brought a huge social and economic burden to the world. Although relevant experts and scholars at home and abroad attach great importance to the prevention and treatment of this disease, there is still a lack of effective therapeutic drugs for this disease. [0003] At present, commonly used clinical drugs for the prevention and treatment of osteoporosis include estrogen replacement drugs, bisphosphonates, selective estrog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58C07J63/00A61P19/10
Inventor 黄蓉江春平吴俊华
Owner 路春芝
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