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G1/G0-phase blocked pentacyclic indol-quinolizidine and compound, antineoplastic activity and application thereof

A technology of cell block and compound, applied in the field of biomedicine, can solve the problem of no blocker successful case and so on

Inactive Publication Date: 2015-12-30
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no successful cases of G1 / G0 phase blockers so far

Method used

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  • G1/G0-phase blocked pentacyclic indol-quinolizidine and compound, antineoplastic activity and application thereof
  • G1/G0-phase blocked pentacyclic indol-quinolizidine and compound, antineoplastic activity and application thereof
  • G1/G0-phase blocked pentacyclic indol-quinolizidine and compound, antineoplastic activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1 prepares L-tryptophan methyl ester hydrochloride (1)

[0021] Add 3.75ml (50mmol) thionyl chloride dropwise to 50ml of anhydrous methanol under ice bath. After the dropwise addition is completed within 30min, add 9.20g (42mmol) L-tryptophan in batches, stir at room temperature for 24h, TLC (CHCl 3 : MeOH=2:3) monitor until the disappearance of the raw material to terminate the reaction. The water pump pumps away the unreacted thionyl chloride SOCl 2 and HCl, and repeatedly triturated with ether to obtain a white solid, recrystallized from methanol-ether to obtain L-tryptophan methyl ester hydrochloride as a colorless solid. The yield is between 85-99%. ESI-MS(m / e)219[M+H] + , physical constants such as melting point and optical rotation are consistent with the reported data.

Embodiment 2

[0022] Example 2 Preparation of 1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline carboxylic acid methyl ester (2)

[0023] In a 250ml round bottom flask, add 20g (78.6mmol) of L-tryptophan methyl ester hydrochloride, 100ml of methanol, add 20ml of trifluoroacetic acid, activate for half an hour, then add 1,1,3,3-tetramethoxy 16ml (97.6mmol) of propane, heated to 80°C with stirring, kept the temperature for 10 hours, and the spots of the raw materials disappeared as monitored by TLC. The reaction solution was cooled to room temperature, and saturated NaHCO was added dropwise. 3 Adjust the pH of the aqueous solution to neutral, recover methanol under reduced pressure, add 100ml of dichloromethane to the residue, and extract the aqueous layer with dichloromethane (50ml×3) after separation, combine the organic layers, dry over anhydrous sodium sulfate, filter, and the filtrate It was concentrated to dryness under reduced pressure, and the residue was purified by silica gel co...

Embodiment 3

[0024] Example 3 Preparation of 1-(2,2-dimethoxyethyl)-3-hydroxymethyl-1,2,3,4-tetrahydrocarboline (3)

[0025] Add 50ml of anhydrous tetrahydrofuran into a 250ml round bottom flask, add LiAlH in batches under stirring 4 0.9g (23.6mmol), activated for half an hour. Dissolve 5g (15.7mmol) of compound (2) in 50ml of anhydrous tetrahydrofuran, then slowly drop it into the reaction flask, raise the temperature to 40°C, keep the reaction for 3 hours, and monitor the disappearance of raw material spots by TLC. Cool the reaction solution to room temperature, add 0.5ml of 15% NaOH aqueous solution, quench the reaction, filter with a Bush funnel to remove the aluminum salt, concentrate the filtrate to dryness under reduced pressure, add ethyl acetate, grind and wash with ether to obtain 2.52g (54%) Compound 3 is a colorless powder. ESI-MS(m / e)291[M+H] + .

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Abstract

The invention discloses G1 / G0-phase blocked pentacyclic indol-quinolizidine which is (6S)-3-acetyl-6-(N-phenylacetyl amino acyl)-oxidative methyl-4,6,7,12-tetrahydro-4-oxoindole-[2,3-1] quinolizidine, and discloses a compound, cell proliferation resistance activity, antineoplastic activity and application thereof.

Description

field of invention [0001] The present invention relates to G1 / G0 phase arrest pentacyclic indoquinazines, i.e. (6S)-3-acetyl-6-(N-phenylacetylaminoacyl)-oxymethyl-4,6,7,12- Tetrahydro-4-oxindole[2,3-a]quinazines, related to their synthesis, related to their anti-cell proliferative activity, and further related to their anti-tumor activity on a mouse transplanted tumor model. The present invention thus relates to (6S)-3-acetyl-6-(N-phenylacetamidoacyl)oxymethyl-4,6,7,12-tetrahydro-4-oxindole[2,3-a] Prospect of clinical application of quinozine as a G1 / G0 phase blocker. The invention belongs to the field of biomedicine. Background technique [0002] Cells produce new cells through proliferation to replace cells lost due to aging, death and trauma, providing the basis for the growth and development of the body and the continuation of the race. The process of cell proliferation is called the cell cycle. Or the cell cycle refers to the process that cells go through from the e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14A61K31/4375A61P35/00
Inventor 彭师奇赵明李春钰
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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