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Oxazolidinone dehydroabietate derivative as well as preparation method and application thereof

A technology of hydroabietic acid oxazolidinone and dehydroabietic acid, which is applied in the field of medicine, can solve the problem that there are no public reports of dehydroabietic acid and oxazolidinone dehydroabietic acid oxazolidinone derivatives, etc. problems, to achieve the effect of improving anti-tumor activity, short preparation cycle and high purity

Active Publication Date: 2018-07-20
GUILIN MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although it has been reported in the existing literature that many structural modifications have been carried out on the dehydroabietic acid core to obtain a series of dehydroabietic acid derivatives, there is no combination of dehydroabietic acid and oxazolidinone to obtain dehydroabietic acid Public reports of oxazolidinone derivatives

Method used

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  • Oxazolidinone dehydroabietate derivative as well as preparation method and application thereof
  • Oxazolidinone dehydroabietate derivative as well as preparation method and application thereof
  • Oxazolidinone dehydroabietate derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of dehydroabietic acid glycidyl ester (compound 2)

[0036] Weigh compound 1 (9g, 29.95mmol), epibromohydrin (4.10g, 32.5mmol) and anhydrous potassium carbonate (9.4g, 1.39mmol) and dissolve it in 40ml of acetone and place it in a round bottom flask at a temperature of 60°C Down, reflux reaction until complete (TLC tracking detection, about 4h), after natural cooling to room temperature, suction filtration, washed with ethyl acetate several times, combined filtrate, concentrated, purified with silica gel column (petroleum ether: ethyl acetate = 10 : 1), obtain light yellow transparent oily liquid 8.85g, productive rate 82.94%.

[0037] Therefore, above-mentioned compound 2 is dehydroabietic acid glycidyl ester, and its structural formula is as shown in the following formula:

[0038]

Embodiment 2

[0039] Example 2: Preparation of 3'-anilino-2'-hydroxydehydroabietic acid propyl ester (compound 3a)

[0040] Weigh compound 2 (120mg, 0.34mmol), aniline (37.99mg, 0.41mmol) and hexahydrate zinc perchlorate (5mg,) were dissolved in 10ml of absolute ethanol and placed in a round bottom flask, at a temperature of 80 ° C, Reflux the reaction until complete (TLC tracking detection, about 1h), after natural cooling to room temperature, concentrate, add 5ml ethyl acetate and 10ml water for extraction, the organic layer is dried overnight with anhydrous sodium sulfate, concentrate, and purify with silica gel column (petroleum ether : Ethyl acetate=10:1), 112.53 mg of white solid 3a was obtained, yield 74.35%. 1 H NMR (600MHz, DMSO) δ7.16(d, J=8.2Hz, 1H), 7.01(s, 1H), 6.97(d, J=7.4Hz, 2H), 6.81(s, 1H), 6.56(d ,J=3.9Hz,2H),6.50(s,1H),5.13(s,1H),4.07(s,1H),3.97(s,1H),3.84(s,1H),3.11(s,1H) ,3.00(s,1H),2.81–2.72(m,3H),2.50(s,1H),2.28(s,1H),2.12(s,1H),1.73(t,J=8.8Hz,3H), 1.64(s,1H),1.58...

Embodiment 3

[0043] Example 3: Preparation of 3'-o-toluidine-2'-hydroxydehydroabietic acid propyl ester (compound 3b)

[0044] Weigh compound 2 (120mg, 0.34mmol), o-toluidine (43.71mg, 0.41mmol) and hexahydrate zinc perchlorate (5mg) were dissolved in 10ml of absolute ethanol and placed in a round bottom flask at a temperature of 80 ° C , reflux reaction to complete (TLC tracking detection, about 1h), naturally cooled to room temperature, concentrated, added 5ml ethyl acetate and 10ml water for extraction, the organic layer was dried overnight over anhydrous sodium sulfate, concentrated, purified with silica gel column (petroleum ether : Ethyl acetate=10:1), 125.63 mg of white solid 3b was obtained, yield 80.49%. 1 H NMR(600MHz,DMSO)δ7.14(s,1H),7.00–6.89(m,3H),6.80(s,1H),6.48(d,J=7.3Hz,2H),5.16(s,1H) ,4.68(s,1H),4.07(s,1H),4.00(s,1H),3.88(s,1H),3.16(s,1H),3.03(s,1H),2.80–2.72(m,3H ),2.49(s,1H),2.27(s,1H),2.11(s,1H),2.04(s,2H),1.75–1.70(m,3H),1.62(s,1H),1.57(s, 1H), 1.32(d, J=12.2Hz, 2H)...

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Abstract

The invention discloses an oxazolidinone dehydroabietate derivative as well as a preparation method and application thereof. The preparation method comprises the following steps: enabling dehydroabietic acid to react with epoxy propane halide to prepare glycidyl ester dehydroabietate; enabling the glycidyl ester dehydroabietate prepared in the above step to react with aromatic primary amine to prepare 3'-aromatic amino-2'-propyl hydroxydehydroabietate; then enabling the 3'-aromatic amino-2'-propyl hydroxydehydroabietate to react with a cyclization reagent to prepare the oxazolidinone dehydroabietate derivative. The prepared oxazolidinone dehydroabietate derivative can be used as an anti-tumor compound. Compared with the prior art, the invention provides a novel preparation method of the oxazolidinone dehydroabietate derivative, and the preparation method is short in preparation period, easy to operate and low in cost; furthermore, the obtained derivative is high in purity and stable inquality; the applicator also finds that a functional group, namely the oxazolidinone, is introduced onto a dehydroabietic acid skeleton, so that the anti-tumor activity of the compound can be improved, and the oxazolidinone dehydroabietate derivative can be used as the anti-tumor compound.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to dehydroabietic acid oxazolidinone derivatives and their preparation methods and applications. Background technique [0002] Cancer is one of the most serious diseases that endanger human health today, and the incidence rate is on the rise. However, most of the current clinical anti-tumor drugs have shortcomings such as high toxicity, poor effect, and multi-drug resistance. Therefore, the research and development is efficient. New anti-tumor drugs with low toxicity are a major problem to be solved urgently. [0003] Dehydroabietic acid, also known as dehydroabietic acid or dehydroabietic acid, is a natural tricyclic diterpene resin acid isolated from disproportionated rosin. It has a structure similar to or similar to many active natural compounds. It also has Good biocompatibility and biodegradability, it has anti-inflammatory, antibacterial, anti-tumor and other biological act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/24A61P35/00
CPCC07D263/24
Inventor 李芳耀王秀庞富华覃翠颕杨新平周异欢马献力
Owner GUILIN MEDICAL UNIVERSITY
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