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1-oxy-2,8-diazacyclononane derivatives and synthetic method thereof

A synthesis method and alkyl technology, applied in the field of medicine, can solve the problems of complex use of raw materials, application limitations, substrate limitations, etc., and achieve the effects of short cycle and simple and easily controllable synthesis method.

Active Publication Date: 2017-02-22
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the diaza nine-membered ring skeleton has always been a difficulty and challenge in organic synthesis, the application of this type of compound has been greatly limited.
The current strategy for synthesizing this nine-membered heterocyclic skeleton can be through a palladium-catalyzed cascade reaction (R.Shintani, K.Ikehata, T.Hayashi, J.Org.Chem.2011,76,4776-4780), multicomponent Tandem reactions (A.F.De la Torre, D.G.Rivera, O.Concepción, R.Echemendia, A.G.Correa, M.W.Paixao, J.Org.Chem.2016, 81, 803-809), etc., but these methods all have limited substrates, functional groups Poor compatibility, and the use of raw materials is more complex and other deficiencies

Method used

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  • 1-oxy-2,8-diazacyclononane derivatives and synthetic method thereof
  • 1-oxy-2,8-diazacyclononane derivatives and synthetic method thereof
  • 1-oxy-2,8-diazacyclononane derivatives and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The 1-oxo-2,8-diazacyclononane derivatives of the present invention were synthesized according to the following synthetic route.

[0052]

[0053] in,

[0054] R 1 stands for hydrogen, C 1～4 Alkyl, C 1～4 Alkoxyl, C 1～4 perfluoroalkyl or halogen atom, or unsubstituted, monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted phenyl, or unsubstituted furyl, or unsubstituted thienyl, or Unsubstituted naphthyl; where the substituent is C 1～4 Alkoxyl, C 1～4 Perfluoroalkyl, C 1～4 Alkyl, cyano or halogen atoms;

[0055] R 2 stands for hydrogen, C 1～4 Alkyl, C 1～4 Alkoxyl, C 1～4 perfluoroalkyl or halogen atom, or unsubstituted, monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted phenyl, or unsubstituted furyl, or unsubstituted thienyl, or Unsubstituted naphthyl; where the substituent is C 1～4 Alkoxyl, C 1～4 Perfluoroalkyl, C 1～4 Alkyl, cyano or halogen atoms;

[0056] R 3 stands for hydrogen, C 1～...

Embodiment 2

[0097] The 1-oxo-2,8-diazacyclononane derivatives of the present invention were synthesized according to the following synthetic route.

[0098]

[0099] in,

[0100] R 1 stands for hydrogen, C 1～4 Alkyl, C 1～4 Alkoxyl, C 1～4 perfluoroalkyl or halogen atom, or unsubstituted, monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted phenyl, or unsubstituted furyl, or unsubstituted thienyl, or Unsubstituted naphthyl; where the substituent is C 1～4 Alkoxyl, C 1～4 Perfluoroalkyl, C 1～4 Alkyl, cyano or halogen atoms;

[0101] R 2 stands for hydrogen, C 1～4 Alkyl, C 1～4 Alkoxyl, C 1～4 perfluoroalkyl or halogen atom, or unsubstituted, monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted phenyl, or unsubstituted furyl, or unsubstituted thienyl, or Unsubstituted naphthyl; where the substituent is C 1～4 Alkoxyl, C 1～4 Perfluoroalkyl, C 1～4 Alkyl, cyano or halogen atoms;

[0102] R 3 stands for hydrogen, C 1～...

experiment example 1

[0117] Experimental example 1: In vitro inhibitory activity test of the 1-oxo-2,8-diazacyclononane derivatives of the present invention on various human tumor strains:

[0118] (1) Cell culture: culture T24, HepG2, NCI-H460, 7702 cells in DMEM medium containing 10% (volume ratio) fetal bovine serum and 1% (volume ratio) double antibody (containing penicillin and streptomycin) , at a temperature of 37°C, 5% CO 2 and 95% air incubator, and change the medium every other day. After the cells were confluent, they were passaged and frozen.

[0119] (2) Seed plate: Take cells in the logarithmic growth phase, remove the old medium, wash twice with PBS, digest the cells with trypsin, add new medium after the cells become round, stop the digestion of the cells and pipette the suspended cells to prepare into a single cell suspension. Take an appropriate amount of cell suspension, add a certain amount of medium to dilute, inoculate into a 96-well plate, 180 μL per well, and the number ...

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Abstract

The invention discloses a series of 1-oxy-2,8-diazacyclononane derivatives and a synthetic method thereof. The 1-oxy-2,8-diazacyclononane derivatives have structures shown by the following formula (I). The synthetic method of the derivatives comprises the following steps of: taking a compound shown by the following formula (II) and a compound shown by the following formula (III), and putting the compounds into an organic solvent to react in the presence of oxygen, thereby preparing a target crude product. The method disclosed by the invention is simple and easy to control, is short in period, and does not need a condition without water and oxygen. The compounds with structures shown by the formulas (I), (II) and (III) are shown in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 1-oxo-2,8-diazacyclononane derivative and a synthesis method thereof. Background technique [0002] The diazacyclononane skeleton is an important core skeleton in natural products and drug molecules, and is an important physiologically active unit, which has important applications in anti-tumor and anti-cancer. Since the diaza nine-membered ring skeleton has always been a difficulty and challenge in organic synthesis, the application of such compounds has been greatly limited. The current strategy for synthesizing this nine-membered heterocyclic skeleton can be through a palladium-catalyzed cascade reaction (R.Shintani, K.Ikehata, T.Hayashi, J.Org.Chem.2011,76,4776-4780), multicomponent Tandem reactions (A.F.De la Torre, D.G.Rivera, O.Concepción, R.Echemendia, A.G.Correa, M.W.Paixao, J.Org.Chem.2016, 81, 803-809), etc., but these methods all have limited substrates, functiona...

Claims

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Application Information

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IPC IPC(8): C07D273/02A61K31/395A61P35/00
CPCA61P35/00C07B2200/07C07D273/02
Inventor 莫冬亮邹宁陈春华冯钰苏桂发
Owner GUANGXI NORMAL UNIV
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