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N-substituted benzothiazolyl-1-substituted phenyl-0, 0-dialkyl-alpha-amino phosphonate ester derivatives preparation and application

An aminophosphonate and substituent technology, applied in the fields of N-substituted benzothiazolyl-1-substituted phenyl-O,O-dialkyl-α-aminophosphonate derivatives and their preparation and use , which can solve the problems of low product yield, reduced amine nucleophilicity, and failure to obtain

Active Publication Date: 2005-10-26
GAUNGXI TIANYUAN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the experiment, it was found that in the α-amino phosphonate, the larger the volume of another substituent at the α-position, the smaller the nucleophilicity of the α-amino group, and the electron-withdrawing substituent will reduce the nucleophilicity of the amine group. When the substituent is an aryl group and there is a nitro substituent on the aryl group, the yield of the product is significantly lower than that of the product in other cases, and when the ortho position of the aryl group is a nitro group, the reaction fails to obtain the expected product

Method used

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  • N-substituted benzothiazolyl-1-substituted phenyl-0, 0-dialkyl-alpha-amino phosphonate ester derivatives preparation and application
  • N-substituted benzothiazolyl-1-substituted phenyl-0, 0-dialkyl-alpha-amino phosphonate ester derivatives preparation and application
  • N-substituted benzothiazolyl-1-substituted phenyl-0, 0-dialkyl-alpha-amino phosphonate ester derivatives preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1, the synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)-O, O-dimethyl-α-aminophosphonate (compound number for a)

[0032] (1) Synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)imine

[0033] Put 2-amino-6-methoxybenzothiazole (4mmol), 4-fluorobenzaldehyde (4mmol) and 15mL toluene into a 25mL three-necked round-bottomed flask with a water trap device, heat to reflux after stirring at room temperature, and Boiling dehydration, followed by TLC (petroleum ether: ethyl acetate = 2:1 volume ratio), the reaction raw material point disappeared after about 1-2h, stop the reaction, directly go to the next step reaction, the resulting solution is N-(6-formazan Oxybenzothiazol-2-yl)-1-(4-fluorophenyl)imine solution. After purification, light yellow crystals were obtained with a yield of 82.4%, m.p.110-112°C, 1 H NMRδ: 3.70(s, 3H, OCH 3 ), 4.05-4.10 (m, 1H, CH), 7.01-7.53 (m, 7H, Ar-H).

[0034] Using the same synthesis method, different sol...

Embodiment 2

[0037] Embodiment two, the synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)-O, O-diethyl-α-aminophosphonate (compound number for b)

[0038] (1) Synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)imine was synthesized according to the method and conditions of Example 1 (1).

[0039] (2) Synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)-O, O-diethyl-α-aminophosphonate

[0040] Synthesized according to the method and conditions of Example 1 (2), only dimethyl phosphite was replaced by diethyl phosphite, the yield was 72.3%, m.p.198-200°C.

Embodiment 3

[0041] Embodiment three, the synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)-O, O-di-n-propyl-α-aminophosphonate (compound number c)

[0042] (1) Synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)imine

[0043] Synthesize as in Example 1 (1) method and conditions.

[0044] (2) Synthesis of N-(6-methoxybenzothiazol-2-yl)-1-(4-fluorophenyl)-O, O-di-n-propyl-α-aminophosphonate

[0045] Synthesized according to the method and conditions of Example 1 (2), only replacing dimethyl phosphite with di-n-propyl phosphite, yield 71.6%, m.p.130-131.5°C.

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Abstract

The present invention discloses a medicine with actions of resisting plant virus and resisting tumor-N-substituted benzothiazolyl-1-substituted phenyl-0.0-dialkyl-alpha- aminophosphonates derivative, its preparation method and biological activity. Said invention also provides its structure formula, and also provides its extensive application for inhibiting tobacco mosaic virus (TMV) activity and inhibiting activity of human body prostatic cancer cell PC3 and others.

Description

technical field [0001] The present invention is N-substituted benzothiazolyl-1-substituted phenyl-O, O-dialkyl-α-aminophosphonate derivatives with anti-plant virus and anti-tumor effects and a preparation method thereof. Background technique [0002] α-aminophosphonate was initially isolated from sheep, and later attracted the attention of researchers. There are a large number of research papers on the synthesis and biological activity of derivatives such as α-aminophosphonate, and its biological activity has also expanded to For details on various aspects of pesticides and medicines, see the review literature on α-aminophosphonates and their synthesis (such as Song Baoan, etc., Research Progress in New Optically Active α-aminophosphonates, Organic Chemistry, 2003, 23 (9) : 933; Song Baoan et al., Synthesis and Biological Activity Research Progress of α-aminophosphonate, Organic Chemistry, 2004, 24(8): 843.). [0003] Yuan Chengye and others reported in 1993, 1998, and 2000...

Claims

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Application Information

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IPC IPC(8): C07F9/6553
Inventor 宋宝安张国平胡德禹逄丽丽杨松刘刚汪华
Owner GAUNGXI TIANYUAN BIOCHEM
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