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Lactone-containing derivative, its pharmaceutical composition and its preparation method and use

A technology of derivatives and compositions, applied in the field of preparing anti-tumor and anti-inflammatory immune drugs, which can solve problems such as drug resistance and insensitivity of tumor stem cells

Active Publication Date: 2021-09-14
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional chemotherapy drugs for tumor treatment have drug resistance problems, especially cancer stem cells are less sensitive

Method used

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  • Lactone-containing derivative, its pharmaceutical composition and its preparation method and use
  • Lactone-containing derivative, its pharmaceutical composition and its preparation method and use
  • Lactone-containing derivative, its pharmaceutical composition and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1 Milicolactone (MCL)

[0065]

[0066] Add 80ml of dichloromethane and p-toluenesulfonic acid (2.0mmol) into a 200ml three-necked flask, add dropwise a solution of parthenolide (PTL, 50mmol) and 18ml of dichloromethane under stirring, and continue to Stir overnight. After TLC confirms complete conversion of the PTL starting material, use NaHCO 3 (0.35g) and 3.5ml of water to prepare a solution, add the reaction solution and stir for 1 hour, during the stirring process, the reaction solution gradually fades from purple to yellow, separate the water phase, wash the organic phase twice with saturated brine, and concentrate to obtain a yellow solid , recrystallized with acetone and cooled at low temperature to obtain light yellow solid MCL (82%).

[0067] 1 H NMR (400MHz, Chloroform-d)δ6.22(s,1H,H-13),5.50(s,1H,H-13),3.82(t,1H,H-12),2.75-2.64(m, 2H,H-3,H-11),2.62(s,1H,OH),2.50-1.25(m,8H,),1.69(s,3H,CH3),1.33(s,3H,CH3).

Embodiment 2

[0068] Example 2 5-Hydroxymimicrolactone (5-OH MCL)

[0069]

[0070] Michelin lactone (MCL) (1.0mmol), SeO 2 (0.3mmol), tert-butyl hydroperoxide TBHP (2.0mmol), 30ml dichloromethane were placed in a 100ml round bottom flask, and refluxed for 3 hours. After filtration through celite, the filtrate was concentrated and separated by column chromatography (eluent) to obtain a yellow solid (52.6%).

[0071] 1 H NMR (400MHz, Chloroform-d): δ6.22(s,1H,H-13),5.52(s,1H,H-13),4.33(s,1H,H-5),3.90-3.82(m ,1H,H-12),3.37(t,J=9.5Hz,1H,H-3),2.91(d,J=12.8Hz,1H,H-11),2.67-1.58(m,11H),1.29 (s,3H, H-15).

Embodiment 3

[0072] Example 3 5-oxo michelactone

[0073]

[0074] Put 5-hydroxymiglianolide (1.0mmol), Dess-Martin reagent (0.5mmol), sodium bicarbonate (10mmol), and 30ml of dichloromethane in a 100ml round bottom flask, and stir at room temperature for 3 hours. After the raw material reaction was completed, quench the reaction with saturated sodium bisulfite solution, add 30ml methylene dichloride, wash the organic phase with water and saturated sodium chloride solution respectively, dry over anhydrous sodium sulfate, concentrate, and separate by column chromatography (eluent ) gave a white solid (93.6%).

[0075] 1 H NMR(400MHz,Chloroform-d)δ6.34(s,1H,H-13),5.61(s,1H,H-13),4.28(t,J=10.0Hz,1H,H-12),3.16 -3.12(m,1H,H-3),3.00(d,J=10.9Hz,1H,H-11),2.76-1.60(m,10H),1.33(s,3H,H-15).

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Abstract

The invention discloses a new class of michelactone derivatives (formula I, II) or salts, its preparation method, its pharmaceutical composition and its use, especially in the preparation of anti-tumor and immunotherapy drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a new class of mimilactone derivatives, a pharmaceutical composition containing them, and their application in the preparation of anti-tumor and anti-inflammatory immune drugs. Background technique [0002] In the past 30 years, although various diagnosis and treatment levels of tumors have been significantly improved, the morbidity and mortality of tumors are still increasing worldwide. According to the forecast of the World Health Organization (WHO), by 2020, the number of cancer cases worldwide will increase to 20 million, and the death toll will reach 12 million. In 2015, 8.2 million people died of cancer worldwide, including 2.8 million in China. Now 7,500 people die of cancer every day in China. China has the highest number of cancer deaths in the world. In China, the prevalence of cancer is 280 per 100,000, showing a trend of rapid growth year by year. The...

Claims

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Application Information

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IPC IPC(8): C07D307/93C07D407/12C07D409/12C07D405/12A61K31/365A61K31/381A61K31/4709A61K31/506A61K31/4025A61K31/4035A61K31/404A61K31/473A61K31/4725A61K31/4184A61P35/00A61P35/02A61P19/02A61P13/12A61P3/10A61P43/00
Inventor 潘显道李燕刘硕霄沈珑瑛杨亚军黄璐璐陈悦邱传将
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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