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Cyclopropane compound as well as preparation method and application thereof

A technology of compound, cyclopropane, which is applied in the field of cyclopropane compounds and their preparation, to achieve the effects of wide sources, low cost and mild conditions

Active Publication Date: 2017-05-10
ZHEJIANG ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compounds reported so far all show affinity for ERβ, and even the pure anti-estrogen substance Fulvestrant (ICI 182780) shows affinity for ERβ, and no specific ligand that only shows affinity for ERα has been found. report

Method used

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  • Cyclopropane compound as well as preparation method and application thereof
  • Cyclopropane compound as well as preparation method and application thereof
  • Cyclopropane compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] 1, Synthesis of 4-benzyloxybenzaldehyde

[0058]

[0059] Add 45g of 4-hydroxybenzaldehyde and 55g of potassium carbonate into a 500ml three-necked flask, perform anhydrous and oxygen-free operation, add 350ml of anhydrous acetone, and stir to dissolve. 52.3ml of benzyl bromide was added into the syringe, and the mixture was refluxed at 65°C for 8h. After the reaction was complete, distilled water was added to quench the reaction. The liquid was separated, the aqueous phase was extracted three times with Ea, the organic phase was washed once with water, dried by adding anhydrous sodium sulfate, concentrated to a small volume, and crystallized by adding Hex. 70.79 g of white crystals were obtained, with a yield of 90.88%.

[0060] 2. Synthesis of 1-(4-(3-chloropropoxy)phenyl)ethanone

[0061]

[0062] Add 34.04g of 4-hydroxyacetophenone and 41.37g of potassium carbonate into a 500ml three-neck flask, perform anhydrous and anaerobic operation, add 250ml of anhydr...

Embodiment 2

[0069] Synthesis of Example 2 (2-(4-(phenylmethoxy)phenyl)-3-phenylcyclopropyl) (4-(3-chloropropoxy)-phenyl)methanone

[0070]

[0071] The obtained (E)-3-(4-(benzyloxy)phenyl)-1-(4-(3-chloropropoxy)phenyl)propenone 19.90g and rhodium acetate 0.22g were added to 500ml three Neck bottle, carry out anhydrous and oxygen-free operation, add 200ml of toluene and stir to dissolve, add 5g of sulfurized cyclohexane, and slowly add 100ml of the toluene solution of diazomethylbenzene obtained dropwise through the constant pressure low liquid funnel, at room temperature 25°C The reaction was stirred for 5 days, and after the reaction was completed, the mixture was filtered through a floxacin funnel, washed with dichloromethane several times, and concentrated to dryness. Column purification, developer: petroleum ether: ether = 5:1. Dichloromethane:petroleum ether=2:1 for recrystallization. Obtained white solid: 7.49g, yield 30.83%.

[0072] The characterization data of this compound...

Embodiment 3

[0073] Example 3 (4-(3-(azetidinyl)propoxy)phenyl)(2-(4-(benzyloxy)phenyl)-3-phenylcyclopropyl)methanol (8a) Synthesis

[0074]

[0075] (2-(4-(Benzyloxy)phenyl)-3-phenylcyclopropyl)(4-(3-chloropropoxy)-phenyl)methanone 740mg, potassium carbonate 221.14mg, iodine Sodium chloride 27mg was placed in a 50ml three-necked bottle, and anhydrous and oxygen-free operation was carried out. 2 Add 5ml of freshly distilled acetonitrile under protection, stir to dissolve, add 0.16ml of arididine into the syringe, and react at 60°C for 24h, TLC (petroleum ether: ethyl acetate: triethylamine = 10:1:0.3%) monitors that the reaction is complete. to room temperature 25°C. Add 10ml of methanol, 32mg of sodium borohydride, stir the reaction at room temperature 25°C for 12h, TLC (petroleum ether: ethyl acetate: triethylamine = 2:1:0.3%) monitors the completion of the reaction, add ice water to quench under ice bath React, let it stand for half an hour, filter, wash the filter cake with disti...

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Abstract

The invention discloses a cyclopropane compound as well as a preparation method and application thereof. The cyclopropane compound has a structure shown as formula I. The cyclopropane compound is prepared by taking a diazo compound and unsaturated ketone as raw materials, reacting in an organic solvent in the presence of a catalyst to obtain a cyclopropane ketone compound, and taking the cyclopropane ketone compound to further react. The preparation method of the cyclopropane compound, disclosed by the invention, has the characteristics of low cost, simplicity in method operation, moderate conditions and the like. The cyclopropane compound disclosed by the invention has affinity on an ER (Oestrogen Receptor) or has selective affinity on different subtypes; the cyclopropane compound is applied to preparation of pharmaceutical preparations for preventing or treating diseases caused by excessive expression and lack or relative shortage of the oestrogen receptor. (The formula I is shown in the description.).

Description

technical field [0001] The invention relates to the technical field of cyclopropane derivatives, in particular to a cyclopropane compound and its preparation method and application. Background technique [0002] The pleiotropic effects of estrogens in mammalian tissues have been documented, and estrogens are now found to affect many organ systems. In addition to the direct effects on the female reproductive system such as ovaries, uterus, and breasts, estrogen can protect the female cardiovascular system, regulate blood lipids, prevent and delay the formation of atherosclerosis, reduce the morbidity and mortality of coronary heart disease (CHD) and improve the Survival rate and quality of life of CHD patients. Estrogen can also improve the activity of bone cells, increase calcium absorption and deposition on bones, reduce bone loss, and promote bone density. [0003] Estrogen exerts its physiological function mainly through the mediation of estrogen receptor (Estrogen Rece...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/088C07D205/04C07D211/14C07D231/12A61P35/00A61P15/00A61P19/10A61P9/10A61P25/00A61P5/28A61P5/30A61P15/08A61P25/16A61P25/28
CPCC07D205/04C07D211/14C07D231/12C07D295/088
Inventor 沈正荣杨叶伟王尊元郑晓亮黄文海马臻
Owner ZHEJIANG ACAD OF MEDICAL SCI
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