Lappaconitine acetal derivative with antineoplastic activity and synthetic method thereof

A technology with anti-tumor activity and high urine, which is applied in the field of medicinal chemistry, can solve problems such as the influence of drug absorption, side effects of bromide ions, and slow analgesic onset, and achieve low production costs, reduced experimental steps, and high conversion rates. Effect

Active Publication Date: 2018-01-05
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, homogenin hydrobromide is insoluble in water, so that the absorption of the drug in the human body is affected, resulting in slow analgesic onset, and free bromide ions have certain side effects in the human body

Method used

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  • Lappaconitine acetal derivative with antineoplastic activity and synthetic method thereof
  • Lappaconitine acetal derivative with antineoplastic activity and synthetic method thereof
  • Lappaconitine acetal derivative with antineoplastic activity and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Condensation products of quinine and 3,4,5-trimethoxybenzaldehyde

[0033] In a 50mL round-bottomed flask, add 100mg of quinine and 67.11mg of 3,4,5-trimethoxybenzaldehyde according to the feeding ratio of 1:2, add a catalytic amount of trimethyl orthoformate and a catalytic amount of phosphotungsten acid, add 25mL toluene as a solvent, stir magnetically at room temperature, and monitor the reaction with thin-layer chromatography. After the reaction is complete, add an appropriate amount of triethylamine to neutralize the reaction solution to neutrality, concentrate the solvent under reduced pressure, and separate and purify by column chromatography to obtain the target compound.

[0034]

[0035] Light yellow amorphous powder 64.91 mg, yield 47.98%. m.p.248~250℃. 1 H-NMR (400MHz, DMSO-d 6 )δ (ppm): 10.55 (1H, s), 8.27 (1H, d, J = 8.3Hz), 7.85 (1H, d, J = 6.4Hz), 7.57 (1H, t, J = 7.1Hz), 7.27 (2H,s),7.17(1H,t,J=8.1Hz),5.80(1H,s),3.87(12H,s),3.77(3H,s),3.41(1H,d,J...

Embodiment 2

[0036] Condensation product of quinine and p-hydroxybenzaldehyde

[0037] In a 50mL round-bottomed flask, add 100mg of quinine and 41.77mg of p-hydroxybenzaldehyde according to the feeding ratio of 1:2, add a catalytic amount of trimethyl orthoformate and a catalytic amount of phosphotungstic acid, and add 25mL of toluene as a solvent , magnetically stirred at room temperature, and monitored the reaction by thin-layer chromatography. After the reaction was complete, an appropriate amount of triethylamine was added to neutralize the reaction solution to neutrality, the solvent was concentrated under reduced pressure, and separated and purified by column chromatography to obtain the target compound.

[0038]

[0039] White amorphous powder 67.32mg, yield 57.15%. m.p.208~210℃. 1 H-NMR (400MHz, DMSO-d 6 )δ (ppm): 10.55 (1H, s), 8.27 (1H, d, J = 8.6Hz), 7.85 (1H, d, J = 8.0Hz), 7.76 (2H, d, J = 8.8Hz), 7.57 (1H,t,J=7.9Hz),7.17(1H,t,J=7.7Hz),6.92(2H,d,J=7.8Hz),5.83(1H,s),5.25(...

Embodiment 3

[0041] Condensation product of quinine and m-hydroxybenzaldehyde

[0042] In a 50mL round-bottomed flask, add 100mg of quinolin and 41.77mg of m-hydroxybenzaldehyde according to the feeding ratio of 1:2, add a catalytic amount of trimethyl orthoformate and a catalytic amount of phosphotungstic acid, and add 25mL of toluene as a solvent , magnetically stirred at room temperature, and monitored the reaction by thin-layer chromatography. After the reaction was complete, an appropriate amount of triethylamine was added to neutralize the reaction solution to neutrality, the solvent was concentrated under reduced pressure, and separated and purified by column chromatography to obtain the target compound.

[0043]

[0044] Light yellow amorphous powder 68.92 mg, yield 56.21%. m.p.218~220℃. 1 H-NMR (400MHz, DMSO-d 6 )δ (ppm): 10.55 (1H, s), 8.27 (1H, d, J = 8.3Hz), 7.85 (1H, d, J = 8.0Hz), 7.58 (1H, dd, J = 6.8, 6.8Hz) ,7.42(1H,t,J=7.7Hz),7.36(1H,d,J=7.5Hz),7.25(1H,m),7.17(1H,t,...

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PUM

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Abstract

A lappaconitine acetal derivative with antineoplastic activity and a synthetic method thereof are disclosed. By using lappaconitine and an aromatic aldehyde derivative as raw materials, an unreportedlappaconitine acetal derivative is synthesized under catalysis of phospho-tungstic acid and trimethyl orthoformate. The synthetic method of the lappaconitine acetal compound has high operational safety and mild reaction conditions, and is suitable for industrial production. It shows through preliminary biological activity tests that the compound has good antineoplastic activity and can be used inthe research on antineoplastic drugs.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a homogenate acetal derivative with antitumor activity and a synthesis method thereof. Background technique [0002] Tumors have seriously threatened human health, and finding effective, safe, and less toxic anti-tumor drugs has always been the goal pursued by tumor drug researchers. With the development of medicinal chemistry, finding natural anti-tumor compounds with high efficiency and low toxicity or carrying out structural modification to synthesize their derivatives has become an important trend in the current anti-tumor drug research. [0003] Hicontin [(1α,14α,16β)-20-ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-[2-(acetylamino)]benzidine Lappaconitine, also known as lappaconitine, is a diterpene alkaloid extracted from the root of Aconitum sinomontanum Nakai, a plant of the Ranunculaceae family. See 1 for its structure. Pharmacological experiments have proved that...

Claims

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Application Information

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IPC IPC(8): C07D491/08A61P35/00
Inventor 梁承远田丹妮贾敏一宋慧慧
Owner SHAANXI UNIV OF SCI & TECH
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