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Multi-substituted amidine compound as well as preparation method and application thereof

A polysubstituted, cyclic amidine technology, applied in the preparation of sulfonic acid amides, organic chemistry, drug combination, etc., can solve problems such as lack of structural diversity

Active Publication Date: 2014-09-03
山东雪地铝业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] These amidines are relatively simple amidines with no more than two substituents on the nitrogen, lacking structural diversity

Method used

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  • Multi-substituted amidine compound as well as preparation method and application thereof
  • Multi-substituted amidine compound as well as preparation method and application thereof
  • Multi-substituted amidine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Under nitrogen protection, 1.0 mmol of allylamine alkyne 9a (R=CH 2 CHCHCO 2 Et, R 1 = H, R 2 =H, n=1), 1.1 mmoles of p-toluenesulfonyl azide, and 1.0 moles of diisopropylethylamine were mixed in 5 ml of toluene, and 0.01 moles of 2-thiazole formic acid copper was added at -30 degrees, Stir and mix evenly. After 5 hours, add 2 ml of saturated ammonium chloride solution, continue stirring for 5 hours, wash with 5 ml of water and 5 ml of saturated saline successively, separate the organic phase and dry it with anhydrous sodium sulfate, filter and remove the organic solvent , add 1 g of 200-mesh silica gel and 6 ml of dichloromethane and mix well, carefully distill off the solvent, put the remaining silica gel on a silica gel column, elute with ethyl acetate / petroleum ether, collect the fractions, and obtain 43% cyclic amidine 7a.

[0045] 7a: Yellow oil, 43%; 1 H NMR (400MHz, CDCl 3 )δ7 . 77(d, J=8.3Hz, 2H), 7.18(d, J=8.0Hz, 2H), 6.01-5.92(m, 1H), 5.60(ddt, J=16...

Embodiment 2

[0047] Under nitrogen protection, 1.0 mmoles of alkyne 9b Mix 1.1 mmol of p-toluenesulfonyl azide and 10.0 moles of diisopropylethylamine in 50 ml of toluene, add 0.10 moles of copper 2-thiazole formate at 60 degrees Celsius, stir and mix evenly, after 10 minutes, add 2 milliliters of saturated ammonium chloride solution, continued to stir for 5 hours, washed successively with 5 milliliters of water and 5 milliliters of saturated saline, separated the organic phase and dried it with anhydrous sodium sulfate, filtered and removed the organic solvent, added 1 gram of 200 mesh silica gel and 6 Mix a milliliter of dichloromethane evenly, carefully distill off the solvent, put the remaining silica gel on a silica gel column, elute with ethyl acetate / petroleum ether, and collect fractions to obtain 96% cyclic amidine 7b.

[0048] 7b: 94%; 1 h NMR (400MHz, CDCl 3 )δ7 . 79(d, J=8 . 2Hz, 2H), 7.20(d, J=8.0Hz, 2H), 7.07(d, J=8.6Hz, 2H), 6.77(d, J=8.7Hz, 2H), 5.89-5.78(m, 1H), ...

Embodiment 3

[0051]

[0052] 7c: 88%; 1 H NMR (500MHz, CDCl 3 )δ7.76(d, J=8.3Hz, 2H), 7.26-7.25(m, 3H), 7.18(d, J=8.1Hz, 2H), 7.14-7.12(m, 2H), 5.85(dddd, J =16.8,10.1,9.1,5.2Hz,1H),5.13-5.09(m,2H),4.75(d,J=14.5Hz,1H),4.53(d,J=14.4Hz,1H),3.90-3.87( m,1H),3.37-3.25(m,2H),3.04-3.01(m,1H),2.37(s,3H),2.31-2.24(m,1H),1.89-1.86(m,2H),1.75- 1.70(m,2H); 13 C NMR (125MHz, CDCl 3 )δ168.8, 141.8, 141.6, 135.9, 135.5, 129.0, 128.7, 128.0, 127.7, 126.0, 117.70, 53.5, 48.2, 36.8, 36.4, 21.7, 21.4, 17.3; HRMS (ESI) m / z theoretical value C 22 h 26 N 2 o 2 SNa + [M+Na] + 405.1607, measured value 405.1601.

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Abstract

The invention discloses a multi-substituted amidine compound, a preparation method and an application thereof and relates to the technical field of pharmaceutical chemistry. The biological activities of the two types of amidines are also subjected to a simple test. The multi-substituted amidine compound disclosed by the invention provides an idea to design amidines drug molecules, broadens the chemical space and diversity of amidine compounds and provides a technical route for the preparation of functionalized amidine derivatives and the multi-substituted amidine compound has vast applications in the technical fields such as biochemical pharmacy and fine chemical industry.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, and relates to two novel amidine compounds, including the preparation and application of the compounds. Background technique [0002] Amidines are an important class of organic compounds. The amidine functional group has special chemical and biological activities, exists in many natural products and drug molecules, and is also used in functional materials. Due to its unique structure, amidines have unique properties and potential uses. However, most of the amidines currently used in the field of medicinal chemistry are simple aromatic amidines with simple and single structures. for example, [0003] (1) Diaryl ethers 1 and 2 have antifungal activity (Molecules2013, 18, 11250-11263; DOI: 10.3390 / molecules180911250). [0004] [0005] (2) Aryl diamidine cations 3 and 4 are effective DNA binding agents (Chem. Sci., 2014, 5, 1901, DOI: 10.1039 / c3sc53317d). [0006] [0007] (3)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/72C07D223/16C07D207/22C07D209/54C07C311/51C07C303/36A61P35/00
CPCC07C311/51C07D207/22C07D209/54C07D211/72C07D223/16
Inventor 徐华栋任杰贾志宏徐科许园元沈美华
Owner 山东雪地铝业科技有限公司
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