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Pseudolarix acid derivatives as well as preparation method and application thereof

A technology of hibiscus bark and its derivatives, applied in the field of medicine, can solve the problems of low bioavailability and poor water solubility, and achieve the effects of stable chemical structure, improved water solubility, and broad-spectrum anti-tumor activity

Inactive Publication Date: 2012-04-11
宋云龙 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as a natural product of traditional Chinese medicine, PAB has poor water solubility and low bioavailability. Therefore, it is necessary to improve its water solubility through chemical structure modification, maintain or even improve its medicinal activity. Research direction of drugs and antifungal drugs

Method used

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  • Pseudolarix acid derivatives as well as preparation method and application thereof
  • Pseudolarix acid derivatives as well as preparation method and application thereof
  • Pseudolarix acid derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Synthesis of SYN-21

[0043] step 1:

[0044] In a 50ml reaction bottle, add 150mg (0.35mmol) of hibiscus bark acetic acid and 2ml of anhydrous dichloromethane, stir to dissolve, then add 4ml of thionyl chloride dropwise at room temperature, install a reflux condenser and CaCl 2 Dry the tube, reflux for 4 hours, evaporate excess thionyl chloride and solvent under reduced pressure, and the residue is dissolved with 2ml of anhydrous dichloromethane to make solution A.

[0045] Step 2:

[0046] In another 50ml reaction bottle, add 410mg (3.5mmol) of N,N-diethylethanolamine and 2ml of anhydrous dichloromethane and stir, then add solution A drop by drop at room temperature, install a drying tube, and stir at room temperature Reacted for 2 hours, detected by TCL, showed that the reaction was complete, and evaporated the low boilers on the rotary evaporator, and the residue was distributed with ethyl acetate and water, and first used NaHCO 3 The solution was was...

Embodiment 2

[0048] Example 2: Synthesis of SYN-22

[0049] At room temperature, add 3ml dimethylformamide, 110mg (0.25mmol) hibiscus bark acetic acid, 69mg (0.5mmol) K 2 CO 3 , 409 mg (2.5 mmol) 4-(3-chloropropyl) morpholine and 0.5 mg of potassium iodide and stirred, loaded with CaCl 2 Dry the tube, raise the temperature to 50°C overnight, and use TCL to detect that the reaction is complete. Pour it into 50 mL of ethyl acetate, wash 20 mL*5 times with saturated brine, and evaporate the ethyl acetate to dryness to obtain the title compound (SYN-22). Crude. The crude product was subjected to column chromatography on a silica gel column with petroleum ether: ethyl acetate: formic acid = 3:1:0.1, and 120.3 mg of the title compound (SYN-22) was isolated (86.1% yield).

[0050] SYN-22: 1 H NMR (CDCl 3 )δ (ppm): 7.21 (m, 1H), 7.15 (1H, d, J = 11.4Hz), 6.54 (1H, dd, J = 15.1, 11.4Hz), 5.88 (1H, d, J = 15.1Hz) , 4.22(2H, t, J=6.5Hz), 3.72(3H, s), 3.71(4H, m), 3.30(1H, d, J=5.0Hz), 3.09(1H, ...

Embodiment 3

[0051] Example 3: Synthesis of SYN-23

[0052] At room temperature, add 110mg (0.25mmol) hibiscus bark acetic acid, 4ml dimethylformamide, 80mg (0.50mmol) of 2-(2-diethylaminoethoxy) ethanol, triphenyl Phosphorus 131mg (0.50mmol), stir to dissolve, slowly add 101mg (0.50mmol) of diisopropyl azodicarboxylate dropwise, connect calcium chloride drying tube, stir at room temperature for 3 hours, use TCL detection to show that the reaction is complete, pour into 50mL In ethyl acetate, wash 20 mL*5 times with saturated brine, and evaporate the ethyl acetate phase to dryness to obtain the crude product of the title compound. The crude product was subjected to column chromatography on a silica gel column, and 122 mg of the title compound was obtained with a yield of 85%.

[0053] SYN-23: 1 H NMR (CDCl 3 )δ (ppm): 7.21 (m, 1H), 7.18 (1H, d, J = 11.4Hz), 6.54 (1H, dd, J = 15.1, 11.4Hz), 5.87 (1H, d, J = 15.1Hz) , 4.30(2H, t, J=4.9Hz), 3.71(3H, s), 3.72(2H, overlapped), 3.59(2H, t, J...

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Abstract

The invention relates to the technical field of medicines and particularly relates to pseudolarix acid derivatives with the structure shown in a formula (1) (the detailed definitions of all groups are shown in the specification). The compounds have favorable activity for various tumor cells such as human lung cancer, colon cancer, breast cancer and the like; besides, the compounds show better antifungal activity. The invention also discloses a composition and preparation method of the pseudolarix acid derivatives as well as the application of the seudolarix acid derivatives in preparation of antitumor medicaments, antifungal medicaments or anti-angiogenesis medicaments.

Description

technical field [0001] The present invention relates to the field of medical technology, more specifically, the present invention relates to a class of hibiscus acid derivatives, and the present invention also relates to the composition and preparation method of such compounds and their use in the preparation of antineoplastic and antifungal drugs the use of. Background technique [0002] Malignant tumors are one of the major diseases that seriously threaten human life and quality of life. At present, most antineoplastic drugs are synthetic drugs, which have the disadvantages of large adverse reactions and immunosuppression. Therefore, finding new anticancer drugs and methods, reducing adverse reactions of chemotherapy, and improving the quality of life of patients has become a hot spot in medical research. Because of their ability to inhibit tumor growth and have less toxic and side effects, traditional Chinese medicines and herbal medicines have received widespread attent...

Claims

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Application Information

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IPC IPC(8): C07D311/94C07D405/12A61K31/366A61K31/5377A61K31/4433A61P35/00A61P31/10A61P9/00
Inventor 邵志宇闫中良宋云龙陈秀华王娟
Owner 宋云龙
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