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Amino Acid Modified s,r-Heptacyclic Aldehyde, Its Synthesis, Activity and Application

A technology based on residues and ethyl groups, which can be used in drug combinations, blood diseases, extracellular fluid diseases, etc., and can solve problems such as increasing adverse reactions

Inactive Publication Date: 2020-10-16
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But precisely because of the high concentration, they quickly reach the plasma and tissues and increase the risk of adverse reactions

Method used

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  • Amino Acid Modified s,r-Heptacyclic Aldehyde, Its Synthesis, Activity and Application
  • Amino Acid Modified s,r-Heptacyclic Aldehyde, Its Synthesis, Activity and Application
  • Amino Acid Modified s,r-Heptacyclic Aldehyde, Its Synthesis, Activity and Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of 1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)

[0018] Under stirring in an ice bath, 150mL CH was added to 5g (17.0mmol) L-Trp-OBzl 2 Cl 2, 5mL 1,1,3,3-tetramethoxypropane, 5mL trifluoroacetic acid. After reacting for 14h, point TLC plate to monitor the disappearance of the raw material point, and a new point is produced (CH 2 Cl 2 :CH 3 OH=30:1), the reaction was terminated. The reaction solution was washed with saturated NaHCO 3 Extract and wash 3 times, extract and wash 3 times with saturated NaCl, combine CH 2 Cl 2 layer, anhydrous NaSO 4 Dry for 2h, filter under reduced pressure, and purify the filtrate with silica gel column chromatography after concentrating under reduced pressure (CH 2 Cl 2 :CH 3 OH=100:1), to obtain 5.87 g (87%) of the title compound as a brown-red oil. ESI-MS(m / e):393[M+H] - .

Embodiment 2

[0019] Example 2 Preparation of 1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid (2)

[0020] In 3.96g (10.0mmol) of 1, add 150mL CH 3 Dissolve OH, add 400mg Pd / C, fill with hydrogen and stir the reaction at room temperature. After 18 hours of reaction, point the TLC plate to monitor the disappearance of the raw material point, and a new point is generated (CH 2 Cl 2 :CH 3 OH=30:1), the reaction was terminated. After vacuum filtration, the filtrate was concentrated under reduced pressure to obtain 2.726 g (8.9 mmol) of a yellow solid, with a yield of 89%. ESI-MS(m / e):303[M-H] - .

Embodiment 3

[0021] Example 3 Preparation of (2S,5S)-tetrahydropyrazine[1,2:1,6]bis{(1S,R)-[1-dimethoxyethyl-2-yl]-2,3, 4,9-tetrahydro-1H-pyridino[3,4-b]indole}-1',4'-dione (3)

[0022] In 886mg (2.91mmol) 2, add 50mL of anhydrous DMF to dissolve, add 1.29g (3.4mmol) HATu, then use collidine to adjust the pH of the reaction solution to 8-9, after 24 hours of reaction, point the TLC plate to monitor the raw materials The point becomes shallower, and a new point is generated (CH 2 Cl 2 :CH 3 OH=60:1), the reaction was terminated; the reaction solution was concentrated under reduced pressure, dissolved in ethyl acetate, and successively washed with saturated NaHCO 3 solution, saturated NaCl solution, 5% KHSO 4 solution, saturated NaCl solution, 5% NaHCO 3 solution, washed with saturated NaCl solution for 3 times, combined the ethyl acetate layers, dried with anhydrous sodium sulfate for 2 h, filtered under reduced pressure, and concentrated the filtrate under reduced pressure to obtain a...

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Abstract

The invention discloses S,R-heptacyclic aldehyde-AA represented by the formula defined in the specification (wherein AA represents L-Ala residue, L-Phe residue, L-Ile residue, L-Leu residue, L-Trp residue, L-Cys residue, L-Asp residue, L-Pyr residue, Gly residue, L-His residue, L-Lys residue, L-Met residue, L-Asn residue, L-Pro residue, L-Gln residue, L-Arg residue, L-Ser residue, L-Thr residue, L-Val residue, and L-Tyr residue), and a preparation method, antiarterial thrombosis activity and activity thereof in inhibition of P-selectin expression in vivo. Therefore, the invention discloses applications of S,R-heptacyclic aldehyde-AA in preparation of antiarterial thrombosis drugs and in preparation of P-selectin antagonists.

Description

technical field [0001] The present invention relates to (2S,5S)-tetrahydropyrazine[1,2:1,6]bis{(1S,1R)-[ethyl-AA]-2,3,4,9-tetrahydro-1H -Pyrido[3,4-b]indole}-1,4-dione, related to its preparation method, related to its anti-arterial thrombosis activity, related to its activity of inhibiting the expression of P-selectin in vivo. Therefore, the present invention relates to their application in the preparation of anti-arterial thrombosis drugs, and their application in the preparation of coagulation P-selectin antagonists. The invention belongs to the field of biomedicine. Background technique [0002] Arterial thrombosis has become a disease with high morbidity and mortality. Since the incidence of arterial thrombosis increases exponentially with age, it poses a particularly serious threat to the health of people in an aging country like my country. If the population base is taken into consideration, the absolute negative impact on my country's national economy and people's...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22A61P7/02
CPCA61P7/02C07D471/22
Inventor 赵明桂琳蒋雪云彭师奇康继勇
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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