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Novel alpha-hederin derivative and preparation method and use thereof

A technology of hedera saponins and derivatives, applied in the field of natural medicine, can solve the problems of unclear hemolytic mechanism, and achieve the effect of reducing hemolytic toxicity

Inactive Publication Date: 2015-07-08
JIANGXI HERBFINE HI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, the mechanism by which saponins cause hemolysis is unclear

Method used

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  • Novel alpha-hederin derivative and preparation method and use thereof
  • Novel alpha-hederin derivative and preparation method and use thereof
  • Novel alpha-hederin derivative and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: 3-O-α-L-rhamnose-(1 → 2)-α-L-arabinose ivy saponin 28-carboxamide (1)

[0041] 1) Synthesis of intermediate A2

[0042]

[0043] The raw material α-hedera saponins (A1) (1.00 g, 1.36 mmol) was dissolved in anhydrous pyridine (10 mL), acetic anhydride (1.3 mL, 13.6 mmol) was added with stirring, and the mixture was stirred at room temperature for 4 hours. After the reaction is over, add 100ml ethyl acetate, adjust pH 4-5 with 10% HCl; wash the organic layer with saturated brine (50 mL×3), dry with anhydrous sodium sulfate, filter, concentrate under reduced pressure to remove the solvent, silica gel column layer After analysis (100 g, petroleum ether-ethyl acetate 2:1), intermediate A2 (white solid 1.30 g) was obtained with a yield of 95.0%. 1 H-NMR (500MHz, CDCl 3 ): δ 5.21(brs, 1H, H-12), 4.97(s, J = 5.0 Hz,1H, H-1''), 4.44(d, J =5.0 Hz, H-1'), 2.14, 2.11, 2.09, 2.05, 2.02, 1.97 (s each, 3H each, 7×CH 3 CO), 1.21(d, J = 5.0 Hz, 3H, H-6``), 1.11, 0.99, 0.95, 0.93...

Embodiment 2

[0051] Example 2: 3-O-α-L-rhamnose-(1 → 2)-α-L-arabinose ivy saponin 28-cyclopropanamide (2)

[0052]

[0053] Intermediate A3 (510.8 mg, 0.5 mmo) was dissolved in anhydrous dichloromethane (10 mL), and cyclopropylamine (44 mg, 0.75 mmol) and triethylamine (101.2 mg, 1.0 mmol) were added under ice cooling, and reacted at room temperature for 12 hours. After the reaction is complete, add 50 mL of dichloromethane, wash with saturated brine (50 mL×3), dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure to remove the solvent to obtain a white solid. The white solid was dissolved in anhydrous methanol (20 mL), sodium methoxide (20 mg) was added, and the mixture was stirred at room temperature for 12 h. After the reaction was completed, the solvent was removed under reduced pressure, and silica gel column chromatography (60 g, dichloromethane: methanol = 8:1) was used to obtain compound 2 (330.2 mg). The yield of the two steps was 81.2%.

[0054] White soli...

Embodiment 3

[0055] Example 3: 3-O-α-L-rhamnanopyranos-(1 → 2)-α-L-arabinose ivy saponin 28-morpholinocarboxamide (3)

[0056]

[0057] The preparation method of compound 3 is similar to that of Example 2, and the yield is 81.4%.

[0058] Compound 3, white solid, melting point 195-197°C. 1 H-NMR (500MHz, pyridine- d 6 ): δ 6.17(s, 1H, H-1''), 5.51(brs, 1H, H-12), 5.06(d, J = 5.0 Hz, H-1'), 3.68-3.86(m, 8H, H-morpholine) 1.73(3H, d, J = 5.0 Hz, H-6``), 1.31, 1.14, 1.10, 1.08, 1.00, 0.96( s each, 3Heach, 6×CH 3 ); 13 C-NMR(125MHz, pyridine- d 6 ): 38.8(C-1), 26.1(C-2), 82.0 (C-3), 44.2(C-4), 48.6(C-5), 18.8(C-6), 33.3 (C-7) , 39.8(C-8), 48.8(C-9), 37.1(C-10), 23.9 (C-11), 122.1(C-12), 145.4(C-13), 42.6(C-14), 28.3(C-15), 24.3(C-16), 46.8(C-17), 42.3(C-18), 46.6(C-19), 30.7(C-20), 34.3(C-21), 33.3 (C-22), 65.2(C-23), 13.5(C-24), 16.2(C-25), 17.4(C-26), 26.1(C-27), 170.7(C-28), 33.4( C-29), 23.9(C-30), 104.7(C-1'), 76.2(C-2'), 74.2(C-3'), 68.9(C-4'), 65.9(C-5') ), 101.9( C-1''), 72.4( C-2``), ...

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Abstract

The invention belongs to the technical field of medicines, in particular relates to a novel alpha-hederin derivative and a preparation method and use thereof, and more particularly relates to a novel alpha-hederin derivative shown in general formula (I) and a preparation method and anti tumor use thereof. Compared with alpha-hederin, the novel alpha-hederin derivative has significant cytotoxicity, hemolytic toxicity is greatly reduced, and the novel alpha-hederin derivative has certain antitumor activity on a tumor-bearing mice model, and can be used for preparing anti-tumor drugs or tumor adjuvant treatment drugs.

Description

technical field [0001] The invention relates to a novel α-hedera saponin derivative and its preparation method and application, belonging to the field of natural medicine. Background technique [0002] In the past 20 years, the incidence of malignant tumors in the world has shown a significant upward trend, and malignant tumors are the main killer of human death. Finding new anti-tumor drugs is the focus and focus of medicinal chemists all over the world, and finding new anti-tumor drugs from natural products is one of the main ways to discover anti-tumor drugs. Triterpene saponins are natural products formed by linking triterpene saponins with sugars, uronic acids, etc. The types of glycoside bonds are mostly ether glycosides formed with C-3 or other hydroxyl groups and ester glycosides formed with 28-position carboxyl groups. Modern research has found that at least 150 natural triterpene saponins derived from more than 100 kinds of plants have potential anti-tumor activit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07H15/256C07H15/26C07H1/00A61P35/00
CPCC07J63/008C07H15/256
Inventor 杨世林陈重朱永明冯育林刘艳丽
Owner JIANGXI HERBFINE HI TECH
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