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4-cyano-6-substituted-2-oxabicyclo[2,2,2]octane derivate and preparation method thereof

A technology for oxabicyclo and derivatives, which is applied in the field of 4-cyano-6-substituted-2-oxabicyclo[2,2,2]octane derivatives and its preparation, and can solve complex and unfavorable rapid screening of compounds Active SAR analysis and other issues to achieve the effect of changing physiological activity, improving drug-like properties, and improving diversity

Active Publication Date: 2012-04-18
SHANGHAI STA PHARMA R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the technical problems that the current oxabicyclic structure is relatively complex, which is not conducive to rapid screening of compound activity and SAR analysis

Method used

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  • 4-cyano-6-substituted-2-oxabicyclo[2,2,2]octane derivate and preparation method thereof
  • 4-cyano-6-substituted-2-oxabicyclo[2,2,2]octane derivate and preparation method thereof
  • 4-cyano-6-substituted-2-oxabicyclo[2,2,2]octane derivate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 : Preparation of ethyl 1-cyano-3-cyclohexene-1-carboxylate

[0039]

[0040]Procedure: Add 20 g of ethyl 2-cyanoacrylate (0.16 mol), 13 g of 1,3-dibutene (0.24 mol) and 200 mg of catalytic amount of hydroquinone in a 100 ml metal can , the mixed solution was heated to 80°C for 5 hours. The mixture was concentrated, and the crude product was purified by column chromatography to obtain 15 g of ethyl 1-cyano-3-cyclohexene-1-carboxylate. (Yield 53%) (wherein petroleum ether ethyl acetate is used as eluent).

[0041] HNMR (400 MHz, CDCl 3 ): δ 5.77~5.80 (m, 1H), 5.63~5.66 (m, 1H), 4.25 (q, J = 7.2 Hz, 2H), 2.49 ~ 2.65 (m, 2H), 2.33~2.37 (m, 1H), 2.14~2.22 (m, 2H), 1.91~2.08 (m, 1H), 1.35 (t, J = 7.2 Hz, 3H).

Embodiment 2

[0042] Example 2 : Preparation of 1-hydroxyethyl-3-cyclohexene-1-carbonitrile

[0043]

[0044] Operation steps: under the condition of nitrogen protection at 0°C, add 61.6 grams of calcium chloride (0.56 moles) to 500 milliliters of ethanol containing 50 grams of ethyl 1-cyano-3-cyclohexene-1-carboxylate (0.28 moles) in solution. Then, at 0°C, 42 g of sodium borohydride (1.1 mol) was added in portions to the reaction solution. After the addition, the mixture was stirred at room temperature (25±5°C, the same hereinafter) for 5 hours, then concentrated hydrochloric acid was added to quench the reaction, the reaction solution was concentrated, and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated to give the crude product. The crude product was purified by column chromatography to obtain 30 g of 1-hydroxyethyl-3-cyclohexene-1-carbonitrile (yield 79%) (with petroleum ether ethyl acetate as eluent).

[0045] HNMR (400 MHz, CDCl ...

Embodiment 3

[0046] Example 3 : Preparation of 1-cyano-3-cyclohexene-1-methyl acetate

[0047]

[0048] Operation steps: 30 grams of 1-hydroxyethyl-3-cyclohexene-1-carbonitrile (0.22 moles) are dissolved in 300 milliliters of pyridine, then the reaction solution is cooled to 0 ° C, and then 45 grams of acetic anhydride (0.44 moles ) was added dropwise to the reaction solution. After the mixture was stirred at room temperature for 5 hours, water was added to quench the reaction. The reaction solution was concentrated and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated to obtain a crude product. The crude product was purified by column chromatography to obtain 35 g of 1-cyano-3-cyclohexene-1-methyl acetate (90% yield) (with petroleum ether ethyl acetate as eluent).

[0049] HNMR (400 MHz, CDCl 3 ): δ 5.79~5.82 (m, 1H), 5.60~5.63 (m, 1H), 4.10 (q, J = 11.2 Hz, 2H), 2.30~2.48 (m, 2H), 2.15~2.20 (m, 1H), 2.14 (s, 3H), 2.04~2.08 (m, 1H), 1....

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PUM

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Abstract

The invention relates to a 4-cyano-6-substituted-2-oxabicyclo[2,2,2]octane derivate and a preparation method thereof, which mainly solve the technical problems that the existing oxabicyclo compounds have complicated structures and are not beneficial to the fast screening of compound activities and an SAR (structure-activity relationship ) analysis. The chemical structural formula is shown in the specification, wherein R1 is a substituted functional group or hydroxy protecting group, and is selected from H, C1-C10 straight chain or one of alkyl, benzyl and alkanoyl containing a substituent side chain. The compound provided by the invention is a medical template compound, and can better satisfy the structural diversity of various enzymes and receptors.

Description

technical field [0001] The invention relates to a 4-cyano-6-substituted-2-oxabicyclo[2,2,2]octane derivative and a preparation method. Background technique [0002] Bridged ring compounds are a class of molecules with special structures, which can effectively link and integrate key pharmacophore units into their rigid structures to form molecules with special spatial configurations / conformations, which can match different biological macromolecules in vivo Many bridged ring compounds have different biological activities, so they have broad application value, especially as template compounds in the process of drug research. Bridged ring compounds containing 2-oxabicyclic structures have been proved by many experiments to have various biological activities. The following are some examples that have been disclosed in some patents and literatures and are closely related to the technology of the present invention. [0003] 2-Oxabicyclo[2,2,2]octane compounds have fragrance and ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61K31/35A61P35/00
CPCY02P20/55
Inventor 郝飞彭宣嘉蔡亚仙胡利红刘君沈余红董径超吴颢吕强马汝建陈曙辉
Owner SHANGHAI STA PHARMA R&D CO LTD
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