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Chirality oliopeptide phosphonate thiourea derivatives and application and preparation method thereof

A technology of thiourea derivatives and peptide phosphonates, applied in the field of chemistry, can solve problems such as unreported synthesis methods, and achieve the effects of good symmetry selectivity, good reliability and simple sources

Inactive Publication Date: 2016-05-25
GUIZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no report on the direct synthesis of chiral oligopeptide phosphonate thiourea derivatives

Method used

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  • Chirality oliopeptide phosphonate thiourea derivatives and application and preparation method thereof
  • Chirality oliopeptide phosphonate thiourea derivatives and application and preparation method thereof
  • Chirality oliopeptide phosphonate thiourea derivatives and application and preparation method thereof

Examples

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Embodiment 1

[0033] Example 1 of the present invention: Synthesis of compound O,O'-diethyl (3-(benzylamino-glycine-L-phenylglycine)-α-thioureido) phenylmethyl phosphate (compound number a):

[0034] (1) Synthesis of O,O'-diethylamino (phenyl) methyl phosphate:

[0035] Benzaldehyde (30mmol, 3.18g) and ammonia (28%, 60mL) were added dropwise to a 100mL dry three-necked flask, and stirred at room temperature for 3h. During this process, white precipitates are produced, which are filtered, washed with dilute ammonia and dried. Under reflux at 75°C and stirring for the reaction, the white solid was transferred to a dry three-necked flask containing diethyl phosphite (15mmol, 2.08g). The solid slowly dissolved, and an intermediate was formed after 8 hours of reaction. Then a mixture of p-toluenesulfonic acid (10mmol, 1.72g) and 50mL of THF was added dropwise to this intermediate, and the reaction was stirred for 10h at below 0°C. A large amount of white solid is generated, filter it, and wash the ...

Embodiment 2

[0054] Example 2 of the present invention: The compound's inhibitory activity test against tobacco mosaic virus (TMV):

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Abstract

The invention provides chirality oliopeptide phosphonate thiourea derivatives and application and a preparation method thereof. A series of chirality oliopeptide phosphonate thiourea derivatives of novel structures are designed and synthesized. Each derivative comprises an amino acid skeleton, a thiourea-based functional group and an amino phosphonate component, and the molecular structure is provided with multiple chirality centers. Meanwhile, the compounds have a good inhibiting effect on plant viruses, and are suitable for preparing plant virus resistant agents and particularly suitable for new pesticide creation and research for tobacco mosaic viruses (TMV). The preparation method is good in reliability, good symmetry selectivity and high yield are achieved, and the material basis is provided for follow-up research. The material source is simple, and the material is easy to obtain, low in cost and good in use effect.

Description

Technical field [0001] The invention relates to the field of chemistry, in particular to a chiral oligopeptide phosphonate thiourea derivative and its application and preparation method. Background technique [0002] As an important natural substance, α-amino acid has good compatibility with the environment and organisms. Its molecules not only have multifunctional groups and typical chiral centers, and are ideal building blocks for the synthesis of chiral drugs, but also amino acid drugs have bactericidal and antiviral properties. , Anti-tumor and other important biological activities (Barrett, GC Chemistry and Biochemistry of the Amino Acids. Chapman and Hall: London, 1985) (Seitz, T.; Wollweber, D. Substituted Valinamide Derivatives [P]. DE4026966, 1992), especially anti-tumor oligopeptides containing amino acid backbone Drug-like drugs have become a new hot spot in tumor treatment research due to their small molecular mass, multiple endogenous targets, easy penetration of tum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/065A01N57/22A01N57/24A01P1/00
CPCA01N57/22A01N57/24C07K5/06191
Inventor 刘静姿何彬胡俊锋廖鹏王永林李勇军宋宝安
Owner GUIZHOU MEDICAL UNIV
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