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Tetrahydro-beta-carbolinyl-3-formyl aliphatic chain amines, and preparation, nano structure, immunosuppression action and application thereof

An immunosuppressive, fatty amine technology, applied in the field of biomedicine, can solve problems such as toxicity

Inactive Publication Date: 2015-07-08
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the 1980s, the discovery and application of effective immunosuppressants such as cyclosporin A and FK506 further prolong the survival time of transplanted organs. However, many effective immunosuppressants have extensive toxicity. Therefore, the development of new immunosuppressants has been a research hotspot in the medical field

Method used

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  • Tetrahydro-beta-carbolinyl-3-formyl aliphatic chain amines, and preparation, nano structure, immunosuppression action and application thereof
  • Tetrahydro-beta-carbolinyl-3-formyl aliphatic chain amines, and preparation, nano structure, immunosuppression action and application thereof
  • Tetrahydro-beta-carbolinyl-3-formyl aliphatic chain amines, and preparation, nano structure, immunosuppression action and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Preparation of 3S-1,1-dimethylol-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid (1)

[0025] Add 6.12 g (30 mmol) of L-tryptophan to 100 mL of water, slowly add concentrated sulfuric acid dropwise in an ice-water bath until the tryptophan is completely dissolved, and then add 3.24 g (36 mmol) of 1,3-dihydroxyacetone. After 24 hours, the reaction solution became turbid, and a solid substance was observed to precipitate out. It was filtered under reduced pressure and washed with distilled water several times to obtain 5.73 g (69%) of the title compound. ESI-MS(m / e): 275[M-H] -

Embodiment 2

[0026] Example 2 Preparation of N-(3S-1,1-dimethylol-2,3,4,9-tetrahydro-β-carboline-3-formyl)-NHC 8 h 17 (2a)

[0027] 1.38g (5.0mmol) 3S-1,1-dimethylol-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid and 1.29g (6.0mmol) CH 3 (CH 2 ) 6 CH 2 NH 2 Dissolve in 20ml of dichloromethane, sonicate. To the resulting solution were added 0.75 g (5.0 mmol) of N-hydroxybenzotriazole (HOBt) and 1.55 g (4.50 mmol) of dicyclohexylcarbodiimide (DCC) under ice cooling. Adjust the pH to 8-9 with N-methylmorpholine (NMM) in an ice bath. Stirred under ice bath for 1 h, then stirred at room temperature for 12 h, TLC (dichloro / methanol=20:1) showed that the product was formed. Dicyclohexylurea (DCU) was filtered off, and 50ml of dichloromethane was added to the filtrate. The resulting solution was sequentially washed with saturated NaHCO 3 Washing with aqueous solution, washing with saturated NaCl aqueous solution, 5% KHSO 4 Washing with aqueous solution and saturated NaCl aqueous solut...

Embodiment 3

[0028] Example 3 Preparation of N-(3S-1,1-dimethylol-2,3,4,9-tetrahydro-β-carboline-3-formyl)-NHC 10 h 21 (2b)

[0029] According to the method of embodiment 2 by 1.38g (5.0mmol) 3S-1,1-dimethylol-2,3,4,9-tetrahydro-beta-carboline-3-carboxylic acid and 1.17g (7.5mmol )CH 3 (CH 2 ) 8 CH 2 NH 2 Obtained 0.32 g (15%) of the title compound as a colorless gum. ESI-MS(m / e): 415[M-H] - .Mp 127-129℃. 1 H-NMR (DMSO-d 6 , 300MHz): δ / ppm=10.58(s, 1H), 8.02(s, 1H), 7.38(d, J=6.0Hz, 1H), 7.32(d, J=3.0Hz, 1H), 7.01(dd, J=6.0Hz, J=3.0Hz, 1H), 6.93(dd, J=3.0Hz, J=6.0Hz, 1H), 4.72-4.62(m, 2H), 3.86-3.83(m, 1H), 3.64- 3.62(m, 1H), 3.58-3.53(m, 3H), 3.14-3.10(m, 2H), 2.88-2.84(m, 1H), 1.52-1.39(m, 2H), 1.38-1.18(m, 14H ), 0.87(t, J=3.0Hz, 3H).

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Abstract

The invention relates to 6 aliphatic chain amine modified carbolinyl carboxylic acid analogs disclosed as general formula I, wherein n is equal to 6, 8, 10, 12, 14 or 16. The invention also relates to a preparation method of the 6 aliphatic chain amine modified carbolinyl carboxylic acid analogs disclosed as general formula I. The invention further relates to a nano structure of the 6 aliphatic chain amine modified carbolinyl carboxylic acid analogs disclosed as general formula I. By researching the inhibiting action of the saturated fatty chain amine modified carbolinyl carboxylic acid analogs on the spleen lymphocyte mitogen breeder reaction and the survival time after transplanting the mouse postotic cardiac muscle, the invention further relates to excellent immunosuppression action of the 6 aliphatic chain amine modified carbolinyl carboxylic acid analogs disclosed as general formula I. The 6 aliphatic chain amine modified carbolinyl carboxylic acid analogs with immunosuppressive activity disclosed as general formula I have wide application prospects in preparing immunosuppressive drugs.

Description

technical field [0001] The present invention relates to six aliphatic chain amine-modified carboline carboxylic acid analogues having immunosuppressive activity, wherein n=6, 8, 10, 12, 14 or 16. The invention also relates to a process for their preparation. The invention further relates to their nanostructures. The present invention further relates to their excellent properties by studying the inhibitory effect of the saturated fatty chain amine-modified carboline carboxylic acid analogs on the mitogen proliferation response of spleen lymphocytes and the survival time of mice after myocardial transplantation. Immunosuppressive effect. The six aliphatic chain amine-modified carboline carboxylic acid analogs of the general formula I having immunosuppressive activity have broad application prospects in the preparation of immunosuppressive drugs. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Thousands of years ago, people had i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/437A61P37/06
Inventor 赵明彭师奇吴建辉王玉记王轶
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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