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Banisterine derivant and uses thereof

A technology of dehydrohalampine and its derivatives, which is applied in the direction of drug combinations, medical preparations containing active ingredients, organic active ingredients, etc., and can solve problems such as high neurotoxicity, high tumor inhibition rate, and no clinical application prospects

Active Publication Date: 2009-05-13
XINJIANG HUASHIDAN PHARMA RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, CN1552711A and WO / 2004 / 106335 disclosed that the chemical structure of dehydrocamelides has been systematically modified, and found that the anti-tumor activity in vivo is significantly improved and the neurotoxicity is significantly reduced. However, these modified compounds The tumor-inhibitory rate of the experimental model of tumor-bearing mice is only 46.9%.
[0005] In summary, most of the existing dehydrohalamine derivatives have no clinical application prospects due to their low antitumor activity or high neurotoxicity. Therefore, an improved dehydrohalamine derivative is urgently needed to meet the clinical need

Method used

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  • Banisterine derivant and uses thereof
  • Banisterine derivant and uses thereof
  • Banisterine derivant and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0323] Example 1 7-Hydroxy-9-ethyl-1-methyl-β-carboline (1)

[0324] Step A: 7-Methoxy-9-ethyl-1-methyl-β-carboline

[0325] Harmline (2.12g, 10mmol), DMF (50ml), 60% NaH (0.6g, 15mmol) were mixed, stirred at room temperature for 10min, added ethyl iodide (15mmol), stirred at room temperature, followed by TLC detection. After the reaction was completed, the reaction mixture solution was poured into 100 ml of ice water, stirred at room temperature for 2 hours, filtered, and washed with a large amount of water to obtain a light yellow solid. Dissolve the above solid in absolute ethanol, adjust the pH to 2 with concentrated hydrochloric acid, then concentrate under reduced pressure to dryness, add water to the absolute ethanol three times to obtain a yellow oil, recrystallize from acetone, and filter to obtain white crystals. Hydrochloride. It was directly used in the next reaction without further purification.

[0326] Step B: 7-Hydroxy-9-ethyl-1-methyl-β-carboline

[0327] ...

Embodiment 2

[0331] Example 2 7-hydroxyl-9-n-butyl-1-methyl-β-carboline (2)

[0332] The operation is the same as in Example 1, but in step A, n-butane iodide is used as the alkylating agent. 2.2 g of white crystals were obtained, yield 87%, mp 205-206°C;

[0333] FAB-MS m / e(M+1)255;

[0334] IR (KBr) 3500-1750, 1618, 1566, 1492, 1451, 1413, 1325, 1238, 1187, 1137, 1112, 980;

[0335] 1 H-NMR (500MHz, DMSO-d 6 )δ 9.72 (1H, s, OH); 8.12-8.13 (1H, d, J=5.0Hz, H-3); 7.95-7.97 (1H, d, J=8.5Hz, H-4); 7.78-7.79 (1H, d, J=5.0Hz, H-5); 6.90-6.91 (1H, m, H-6); 6.72-6.75 (1H, m, H-8); 4.41-4.44 (2H, m, NCH 2 CH 2 CH 2 CH 3 ); 2.91 (3H, s, CH 3 ); 1.67-1.74 (2H, m, NCH 2 CH 2 CH2 CH 3 ); 1.36-1.40 (2H, m, NCH 2 CH 2 CH 2 CH 3 ); 0.92-0.94 (2H, m, NCH 2 CH 2 CH 2 CH 3 ).

Embodiment 3

[0336] Example 3 7-Hydroxy-9-isobutyl-1-methyl-β-carboline (3)

[0337] The operation was the same as in Example 1, except that 1-iodo-2-methylpropane was used as the alkylating agent in step A. 2.0 g of white crystals were obtained, yield 79%, mp 246-248°C;

[0338] FAB-MS m / e(M+1)255;

[0339] IR (KBr) 3500-1750, 1626, 1568, 1447, 1392, 1203, 1136, 977, 820;

[0340] 1 H-NMR (500MHz, DMSO-d 6 )δ 9.70 (1H, s, OH); 8.13-8.14 (1H, d, H-3); 7.95-7.97 (1H, d, H-4); 7.79-7.80 (1H, d, H-5); 6.93 (1H, s, H-6); 6.72-6.74 (1H, d, H-8), 4.26-4.27 (2H, d, NCH 2 CH[CH 3 ] 2 ); 2.90 (3H, s, CH 3 ); 2.11-2.17 (1H, m, NCH 2 CH[CH 3 ] 2 ); 0.85-0.87 (6H, s, NCH 2 CH[CH 3 ] 2 ).

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Abstract

The invention relates to a yageine derivative and salts of compounds. The invention synthesizes the novel yageine derivative compounds which can strengthen the antineoplastic activity and reduce the toxicity of a nervous system through the structural modification to locus 1, 2, 3, 7 and 9 of beta-carboline parent nuclei of yageine. The compounds can be used for preparing drugs used to treat various tumor diseases through the screening study of in vivo and in vitro anti-tumor experimental models.

Description

Technical field [0001] The present invention belongs to the field of pharmaceutical compounds, which relates to β-carboline alkaloid compounds and their applications, and more specifically, to dehydrocameline derivatives and their applications in anti-tumor drugs. Background technique [0002] Dehydrocameline and its analogues have a wide range of pharmacological effects, mainly in two aspects: neural activity and anti-tumor activity. The neuroactivity of dehydrocameline and its derivatives is mainly manifested in its excitatory effect on the cerebral cortex, motor center, spinal cord, etc., which can cause hallucinations, tremors, paroxysmal convulsions, excitement of the pons, and certain specific movements and limbs. Stiffness; In the study of the anti-tumor effect of total alkaloids extracted from Camelina seeds, it was found that two mixed alkaloids, dehydrocameline and cameline, had significant effects on six types of human tumor cell lines cultured in vitro. It has a...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61P35/00
Inventor 曹日晖武嘉林于富生王子厚彭文烈
Owner XINJIANG HUASHIDAN PHARMA RES
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