Dimethyl tetrahydrocarboline-3-formyl-Ile-AA, and synthesis, activity and application thereof

A technology of dimethyl and carboline, applied in the field of biomedicine

Inactive Publication Date: 2017-01-11
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

They all have side effects such as bleeding and gastrointestinal irritation

Method used

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  • Dimethyl tetrahydrocarboline-3-formyl-Ile-AA, and synthesis, activity and application thereof
  • Dimethyl tetrahydrocarboline-3-formyl-Ile-AA, and synthesis, activity and application thereof
  • Dimethyl tetrahydrocarboline-3-formyl-Ile-AA, and synthesis, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of (3s)-1,1-dimethyl-tetrahydro-β-carboline-3-carboxylic acid (1)

[0018] Weigh 4.08g (20mmol) of L-Trp into a 250mL eggplant bottle, and slowly add 80mL of acetone. Under ice-bath stirring conditions, 4 mL of concentrated hydrochloric acid was added to the suspension reaction solution, and then 2 mL of distilled water was added, and after stirring for 0.5 h, the ice-bath was removed for 24 h. After 24h, the raw material spot monitored by thin layer chromatography disappeared. The hydrogen chloride gas in the reaction solution was pumped out by a water pump and the reaction solution was concentrated. After adding 100 mL of ether, it was allowed to stand still to obtain 5.22 g (93%) of the title compound as colorless crystals. ESI-MS(m / e)245.1212[M+H] + .

Embodiment 2

[0019] Example 2 Preparation of (3s)-1,1-dimethyl-tetrahydro-β-carboline-3-formyl-Ile-Ala-OBzl(2a)

[0020] Under ice bath and stirring, add 135mg (1mmol) N-hydroxyl to a solution of 281mg (1mmol) (3s)-1,1-dimethyl-tetrahydro-β-carboline-3-carboxylic acid and 20mL anhydrous tetrahydrofuran Benzotriazole, 207 mg (1 mmol) of dicyclohexylcarbonyl diimide and 281 mg (1 mmol) of Ile-Ala-OBzl, the pH of the reaction solution was adjusted to 9 with N-methylmorpholine. The reaction was carried out in an ice bath for 0.5h, and then it was reacted at room temperature until TLC (petroleum ether:acetone, 2:1) to monitor the completion of the reaction. The generated dicyclohexylurea was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue obtained was dissolved in 30 mL of ethyl acetate. The ethyl acetate solution was washed 3 times with saturated sodium bicarbonate aqueous solution and 3 times with saturated sodium chloride aqueous solution. % Potassi...

Embodiment 3

[0021] Example 3 Preparation of (3s)-1,1-dimethyl-tetrahydro-β-carboline-3-formyl-Ile-Asp(OBzl)-OBzl(2b)

[0022] According to the method of Example 2 from 1.12g (4mmol) (3s)-1,1-dimethyl-tetrahydro-β-carboline-3-carboxylic acid and 1.70g (4mmol) Ile-Asp(OBzl)-OBzl This gave 681 mg (26%) of the title compound as a pale yellow solid. Mp: 91-92°C; ESI-MS(m / e)653[M+H] + ; 1 H-NMR(300MHz, CDCl 3 ): δ / ppm = 7.80 (s, 1H), 7.62 (d, J = 9.0 Hz, 1H), 7.51 (d, J = 6.0 Hz, 1H), 7.35 (m, 10H), 7.15 (m, 2H) , 6.90 (d, J = 9.0 Hz, 1H), 5.13 (dd, J = 3.0, 18.0 Hz, 4H), 4.99 (m, 1H), 4.39 (dd, J = 6.0, 9.0 Hz, 1H), 3.76 ( dd, J = 6.0, 12.0 Hz, 2H), 3.31 (dd, J = 6.0, 15.0 Hz, 1H), 3.02 (m, 2H), 2.68 (dd, J = 12.0, 15.0 Hz, 1H), 1.95 (m , 1H), 1.61 (m, 2H), 1.54 (s, 3H), 1.47 (s, 3H), 1.20 (m, 2H), 0.95 (m, 6H).

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PUM

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Abstract

The invention discloses (3s)-1,1-dimethyl-tetrahydro-beta-carboline-3-formyl-Ile-AA represented by the following formula defined in the specification (in the formula, AA represents Ala residues, Asp residues, Phe residues, Ile residues, Leu residues, Met residues, Ser residues, Thr residues, Val residues, Trp residues or The residues). The invention discloses a preparation method and antithrombotic activity of the (3s)-1,1-dimethyl-tetrahydro-beta-carboline-3-formyl-Ile-AA; therefore, an application of the (3s)-1,1-dimethyl-tetrahydro-beta-carboline-3-formyl-Ile-AA in preparation of antithrombotic drugs is disclosed.

Description

Technical field [0001] The present invention relates to (3s)-1,1-dimethyl-tetrahydro-β-carbolinecarboxyl-Ile-AA, relates to their preparation method, relates to their antithrombotic activity in SD rats, and therefore relates to it As an antithrombotic drug application. The invention belongs to the field of biomedicine. Background technique [0002] Coronary heart disease, stroke and vasculitis are very common cardiovascular and cerebrovascular diseases. With the continuous improvement of people's living standards, the number of cardiovascular and cerebrovascular diseases is increasing year by year. Risk factors for cardiovascular and cerebrovascular diseases are prevalent, and the prevalence of cardiovascular and cerebrovascular diseases in my country continues to rise. According to statistics, there is 1 out of 5 adults with cardiovascular disease. Thrombosis is an important cause of cardiovascular and cerebrovascular diseases. The prevention of thrombosis still depends on ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/097A61K38/06A61P7/02
Inventor 赵明彭师奇吴建辉王玉记陈航
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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