N-heterocyclic condensed tryptamine-beta-lactam derivative as well as preparation method and application thereof

A technology for synthesizing tryptamine and its derivatives, which is applied in the field of N-heterocyclic fused tryptamine-β-lactam derivatives and its preparation, achieving the effects of mild reaction, simple operation and high yield

Inactive Publication Date: 2020-08-14
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Combining tryptamine and β-lactam to synthesize a new type of tryptamine-β-lactam deriv

Method used

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  • N-heterocyclic condensed tryptamine-beta-lactam derivative as well as preparation method and application thereof
  • N-heterocyclic condensed tryptamine-beta-lactam derivative as well as preparation method and application thereof
  • N-heterocyclic condensed tryptamine-beta-lactam derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] This example describes the N-heterocyclic fused tryptamine-β-lactam derivative 6a and its preparation method, R in compound 6a 1 is phenyl, R 2 For benzyl, the name of compound 6a is 1-(2-(1H-indol-3-yl)ethyl)-N-benzyl-3-methylene-4-oxo-2-phenylazepine Cyclobutane-2-carboxamide, its chemical structural formula is as follows:

[0050]

[0051] The preparation method of compound 6a is as follows:

[0052] At room temperature, add 1.00 mmol benzaldehyde and 1.00 mmol propiolic acid into a microwave bottle (10 mL) containing 2 mL methanol and stir for 5 minutes, then add 1.00 mmol tryptamine and 1.00 mmol benzyl isonitrile and stir the reaction overnight. The isonitrile was determined by layer chromatography to disappear, and the reaction was completed. The solvent methanol was removed under a gentle nitrogen flow, and the obtained residue was dissolved in 3.0 mL of acetonitrile, and 2.0 mmol K 2 CO 3 , sealed and placed in a microwave oven at 120 ° C for 10 min, coo...

Embodiment 2

[0055] This example describes the N-heterocyclic fused tryptamine-β-lactam derivative 6b and its preparation method, R in compound 6b 1 is 4-fluorophenyl, R 2 For benzyl, the name of compound 6b is 1-(2-(1H-indol-3-yl)ethyl)-N-benzyl-2-(4-fluorophenyl)-3-methylene-4 -Oxazetidine-2-carboxamide, its chemical structural formula is as follows:

[0056]

[0057] The preparation method of compound 6b is as follows:

[0058] At room temperature, 1.00 mmol of 4-fluorobenzaldehyde and 1.00 mmol of propiolic acid were added to a microwave bottle (10 mL) containing 2 mL of methanol and stirred for 5 minutes, followed by addition of 1.00 mmol of tryptamine and 1.00 mmol of benzyl isonitrile and stirred overnight, The disappearance of isonitrile was determined by thin-layer chromatography, and the reaction was completed. The solvent methanol was removed under a gentle nitrogen flow, and the obtained residue was dissolved in 3.0 mL of acetonitrile, and 2.0 mmol K 2 CO 3 , sealed and ...

Embodiment 3

[0061] This example describes the N-heterocyclic fused tryptamine-β-lactam derivative 6c and its preparation method, R in compound 6c 1 is 4-chlorophenyl, R 2 For benzyl, the name of compound 6c is 1-(2-(1H-indol-3-yl)ethyl)-N-benzyl-2-(4-chlorophenyl)-3-methylene-4 -Oxazetidine-2-carboxamide, its chemical structural formula is as follows:

[0062]

[0063] The preparation method of compound 6c is as follows:

[0064] At room temperature, 1.00 mmol of 4-chlorobenzaldehyde and 1.00 mmol of propiolic acid were added into a microwave bottle (10 mL) containing 2 mL of methanol and stirred for 5 minutes, followed by addition of 1.00 mmol of tryptamine and 1.00 mmol of benzyl isonitrile and stirred overnight, The disappearance of isonitrile was determined by thin-layer chromatography, and the reaction was completed. The solvent methanol was removed under a gentle nitrogen flow, and the obtained residue was dissolved in 3.0 mL of acetonitrile, and 2.0 mmol K 2 CO 3 , sealed an...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to an N-heterocyclic condensed tryptamine-beta-lactam derivative as well as a preparation method and application thereof. The preparation method comprises the following steps: adding an aldehyde compound and propiolic acid into methanol and stirring; then adding tryptamine and isocyanide, and reacting under stirring;removing the methanol in a nitrogen atmosphere; dissolving obtained residues in acetonitrile, adding K2CO3, sealing the mixture, heating the mixture in a microwave oven, removing the acetonitrile, diluting with ethyl acetate, washing with saline water, drying with sodium sulfate, concentrating, purifying the obtained concentrate by silica gel column chromatography, and drying to obtain the N-heterocyclic condensed tryptamine-beta-lactam derivative. The N-heterocyclic fused tryptamine-beta-lactam derivative has a certain inhibition effect on the cell viability of liver cancer, breast cancer, head and neck squamous cell carcinoma and colon cancer cell lines, can inhibit or kill tumor cells, has antitumor activity, and can be applied to preparation of antitumor drugs.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to N-heterocyclic fused tryptamine-β-lactam derivatives and their preparation methods and applications. Background technique [0002] Tumor has become one of the main culprits of global disease death, a disease that seriously threatens human health and social development. At present, Western medicine has many methods for the treatment of tumors: (1) surgical treatment, which is easy to relapse and difficult to predict; (2) chemical drug treatment, which has the disadvantages of large side effects and damage to liver function; (3) radiotherapy; suitable for cancer conditions Relatively stable, no metastases, and patients without other complications; (4) Biological therapy; some biological response modifiers can enhance the patient's resistance, achieve the purpose of killing and inhibiting cancer cells, and can be used in combination with chemotherapy, although Biological ...

Claims

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Application Information

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IPC IPC(8): C07D403/06A61P35/00
CPCA61P35/00C07D403/06
Inventor 高丽霞李世强唐艳
Owner CHONGQING UNIV OF ARTS & SCI
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