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Dehydrogenation zaluzanin C derivative and preparation method and application thereof

A technology for dehydro mesothrin and derivatives, applied in the field of medicine, can solve the problem of no dehydro mesothrin C derivatives and the like

Active Publication Date: 2016-06-08
SHANGHAI UNIV OF T C M
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are relatively few reports about it, so there is no relevant report about dehydromesthrin C derivatives

Method used

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  • Dehydrogenation zaluzanin C derivative and preparation method and application thereof
  • Dehydrogenation zaluzanin C derivative and preparation method and application thereof
  • Dehydrogenation zaluzanin C derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the preparation of compound II-5

[0046] In a 25mL double-necked flask, add dehydromethrin C (24.4mg, 0.1mmol / Lol), 4-(trifluoromethyl)piperidine (16.9mg, 0.11mmol / Lol), and then add 2mL of acetonitrile, Under the condition of stirring, triethylamine (0.11mmol / Lol, 16.0μL) was added to the reaction system, and the reaction was refluxed for 12h under the protection of argon to complete the reaction. The reaction solution was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was added Dichloromethane 10mL, stirred to obtain a mixed solution, then the mixed solution was washed successively with 0.5mol / L hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine each 5mL, the organic phase was separated and dried with anhydrous sodium sulfate, filtered , and the filtrate was concentrated to obtain a crude product, which was purified by column chromatography with a mixed solvent of DCM:methan...

Embodiment 2

[0050] Embodiment 2: the preparation of compound III-6

[0051]

[0052] a) Add dehydromethrin C (24.4mg, 0.1mmol / Lol) and 5mL methanol solvent into a 25mL double-necked flask, and add NaBH to the reaction system under stirring 4 (6mg, 0.15mmol / L), stirred at room temperature for 2h under argon protection, ended the reaction, and added 1mL, 1.0mol / L NaHSO 4 The solution was quenched, and after stirring for 10 min, the organic phase was separated, the aqueous phase was extracted with ethyl acetate (4×5 mL), the organic phases were combined, washed with 5 mL of saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated , to obtain the crude product, the crude product was purified by column chromatography with a mixed solvent of petroleum ether:ethyl acetate=3:2 (volume ratio), to obtain 22.7 mg of white solid compound, i.e. intermediate III-A (molar yield was 92.3 %);

[0053] b) Add intermediate III-A (20.0mg, 0.08mmol / Lol) and 1mL py...

Embodiment 3

[0058] Embodiment 3: Preparation of Compound II-5 and Compound III-6 Tablets

[0059] After mixing each 10 g of compound II-5-HCl and compound III-6-MA in the dehydromethrin C derivative with 87.5 g (Baihujing: lactose=7:3, mass ratio), add 95 % ethanol granulation, drying, granulation (screening), adding 2.5g of sodium stearate and mixing evenly, then tableting to obtain a weight of 200 mg per tablet, the content of compound II-5-HCl or compound III-6-MA is equal to In the form of 10mg tablets.

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PUM

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Abstract

The invention discloses a dehydrogenation zaluzanin C derivative and a preparation method and application thereof. The dehydrogenation zaluzanin C derivative is a compound of a structure as indicated in formula I or medically acceptable salt of the compound, tautomer, stereisomer or a precursor compound. The dehydrogenation zaluzanin C derivative is obtained by conducting chemical modification on dehydrogenation zaluzanin C. It is indicated by experiments that the dehydrogenation zaluzanin C derivative has a remarkable anti-inflammatory function, especially for acute peritonitis, is expected to be developed as an anti-inflammatory drug, especially as the anti-inflammatory drug for treating acute peritonitis and has medicinal value.

Description

technical field [0001] The invention relates to a dehydrosemithrin C derivative, a preparation method and application thereof, and belongs to the technical field of medicine. Background technique [0002] Natural products are of great significance for the discovery, design and synthesis of new drugs, and are also an important source of biologically active substances and innovative drugs. According to literature reports: Since 1940, 42% of the anticancer chemotherapy drugs marketed in the world are directly derived from natural products, such as: Taxol, Docetaxel, Vinorelbine, Hydroxycamptothecin (camptothecin), artemisinin (Artemisinin), etc., 30% are derivatives or analogs of natural products. The advantage of developing natural products as drug sources is that biosynthesized natural product small molecule SMNPs have better biocompatibility with enzymes and receptors, and are more likely or suitable to become lead compounds for therapeutic drugs. my country's traditional ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93C07D405/06A61P29/00
CPCC07D307/93C07D405/06
Inventor 郑月娟季光秦向阳何伟刚姜昕秦艺菲王于莉
Owner SHANGHAI UNIV OF T C M
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