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Perillyl alcohol derivatives and their preparation and application

A derivative, perillyl alcohol technology, applied in the field of perillyl alcohol derivatives, can solve the problems of low bioavailability of oral administration, poor water solubility of perillyl alcohol, limited clinical application and the like, and achieves a simple and feasible preparation method, good resistance Cancer active, easy-to-operate effect

Active Publication Date: 2018-02-16
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Perillyl alcohol has poor water solubility and low oral bioavailability, which limits its clinical application (Liu G, Oettel K, Ummersen L V,, et al. Phase II trial of perilly alcohol (NSC641066) administered daily in patients with metastatic androgen independent prostate cancer[J].Investigational New Drugs,2003,21(3):367-372.Bailey H H,Attia S,Love R R,etal.Phase II trial of daily oral perillyl alcohol(NSC641066)in treatment-refractory metastatic breast cancer[ J]. Cancer Chemother Pharmacol, 2008, 62(1): 149-157.)

Method used

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  • Perillyl alcohol derivatives and their preparation and application
  • Perillyl alcohol derivatives and their preparation and application
  • Perillyl alcohol derivatives and their preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1 perillyl alcohol Synthesis

[0026] Dissolve 0.1 mol perillaldehyde in 100 mL of absolute ethanol, add 0.2 mol NaBH in batches under ice-cooling 4 , After the addition was completed, the reaction was carried out at room temperature for 3h. Distill ethanol off under reduced pressure, add 30mL water and 30mL dichloromethane, transfer to a separatory funnel, separate the organic phase, extract the water phase with dichloromethane, combine the organic phases, wash with water and saturated brine, and dry over anhydrous sodium sulfate . After concentration, perillyl alcohol was obtained as a colorless transparent liquid with a yield of 86.8%.

Embodiment 2

[0027] Example 2 Synthesis

[0028] Add 25 mL of acetic anhydride dropwise to a solution of 0.08 mol of the product of Example 1 in 25 mL of pyridine, and react at room temperature for 4 h. Add 2 mL of methanol and 50 mL of ethyl acetate, transfer to a separatory funnel, separate the organic phase, wash with saturated sodium bicarbonate and saturated brine, and dry over anhydrous sodium sulfate. Concentrate to obtain a colorless transparent liquid with a yield of 95.4%.

Embodiment 3

[0029] Example 3 Synthesis

[0030] Dissolve 0.06mol of the product of Example 2 and 0.09mol of glacial acetic acid in 150mL of dichloromethane, and slowly add 0.24mol of sodium hypochlorite aqueous solution (containing 10% available chlorine) dropwise under ice cooling. After the addition, the reaction was continued for 30 minutes. Add 50mLNa 2 SO 3 aqueous solution, the organic layer was separated, the aqueous layer was extracted with dichloromethane, the organic phases were combined, washed with water and saturated NaCl solution, and dried over anhydrous sodium sulfate. Concentrate to obtain a light yellow liquid with a yield of 85.9%.

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Abstract

The invention belongs to the technical field of medicine, and relates to a series of perilla alcohol derivatives disclosed as Formula I, and preparation and application thereof. The invention also relates to pharmaceutically acceptable salts and solvates of the perilla alcohol derivatives, and a pharmaceutical composition containing the perilla alcohol derivatives or pharmaceutically acceptable salts thereof as active components, which can be used for treating cancers. The perilla alcohol derivatives and pharmaceutical salts thereof have favorable anticancer activity. The preparation method is simple and feasible, and is easy to operate.

Description

Technical field: [0001] The present invention relates to a series of novel perillyl alcohol derivatives, salts of the compound and pharmaceutical compositions containing the compound or the salts as active ingredients, which can be used for treating cancer. The invention also relates to the preparation method of a series of intermediates of perillyl alcohol derivatives. Background technique: [0002] Perillyl alcohol (perillyl alcohol) is the volatile oil of isoprene terpene, which is widely found in perilla leaves, citrus, cherry, mint and other plants. It can induce apoptosis, inhibit tumor cell proliferation, and induce tumor cell redifferentiation. It is one of the few natural products known to have both chemopreventive and chemotherapeutic effects on tumors (Hu Dong, Chen Yan. The anticancer effect of food source monoterpene perillyl alcohol[J]. Clinical Blood Journal , 2001, 14(3):141-143). In the initial stage of tumor formation, perillyl alcohol can not only reduce...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/04C07D295/096C07D209/20C07D213/74C07D239/42C07C215/26C07C213/00
CPCC07C213/00C07C215/26C07D209/20C07D213/74C07D239/42C07D241/04C07D295/096
Inventor 惠子董金华张美慧夏明钰徐莉英
Owner SHENYANG PHARMA UNIVERSITY
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