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Method for improving water solubility of tryptanthrin (TRYP), tryptanthrin derivative, as well as preparation method and application of tryptanthrin derivative

A technology of tryptanthrin activity and tryptanthrin, which is applied in drug combinations, nervous system diseases, sensory diseases, etc., can solve the problems of increasing the water solubility of tryptanthrin, shorten the reaction time, increase the fat solubility, and increase the yield. high effect

Active Publication Date: 2019-07-23
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, increasing the aqueous solubility of tryptanthrin remains challenging

Method used

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  • Method for improving water solubility of tryptanthrin (TRYP), tryptanthrin derivative, as well as preparation method and application of tryptanthrin derivative
  • Method for improving water solubility of tryptanthrin (TRYP), tryptanthrin derivative, as well as preparation method and application of tryptanthrin derivative
  • Method for improving water solubility of tryptanthrin (TRYP), tryptanthrin derivative, as well as preparation method and application of tryptanthrin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Step (1): Synthesis of 5-methylisatoic anhydride

[0044]

[0045] Please refer to the above formula, suspend 1000.0mg (6.213mmol) of 5-methylisatin 1 in 20mL of dry dichloromethane, add 2522.8mg (14.62mmol) of m-chloroperoxybenzoic acid at 0°C, and Stirred under 4 hours; After TLC detects that the reaction is completed, the orange solid obtained by the filtration reaction is washed with (5mL x 3) ethyl acetate to obtain 5-methylisatoic anhydride 2;

[0046] Step (2): Synthesis of 2-methyl-8-fluorotryptanthrin

[0047]

[0048] Please refer to the above formula, suspend 1000.0mg (5.650mmol) of 5-methylisatoic anhydride 2 and 932.9mg (5.650mmol) of 5-fluoroisatin in 10mL of dry acetonitrile solvent, add 2.35mL of triethylamine , heated and stirred at 82°C to 90°C for 4 to 4.5 hours, cooled to room temperature, filtered, and the filter cake was washed with (5mL×3) methanol to obtain a yellow-green solid, namely 2-methyl-8-fluorotryptanthrin 3;

[0049] Characteriz...

Embodiment 2

[0057] Step (1): Synthesis of 5-methylisatoic anhydride

[0058]

[0059] Please refer to the above formula, suspend 1000.0mg (6.213mmol) of 5-methylisatin 1 in 20mL of dry dichloromethane, add 1261.4mg (6.213mmol) of m-chloroperoxybenzoic acid at 0°C, and Stirred under 4 hours; After TLC detects that the reaction is completed, the orange solid obtained by the filtration reaction is washed with (5mL x 3) ethyl acetate to obtain 5-methylisatoic anhydride 2;

[0060] Step (2): Synthesis of 2-methyl-8-fluorotryptanthrin

[0061]

[0062] Please refer to the above formula, suspend 1000.0mg (5.650mmol) of 5-methylisatoic anhydride 2 and 932.9mg (5.650mmol) of 5-fluoroisatin in 10mL of dry acetonitrile solvent, add 0.94mL of triethylamine , heated and stirred at 82°C to 90°C for 4 to 4.5 hours, cooled to room temperature, filtered, and the filter cake was washed with (5mL×3) methanol to obtain a yellow-green solid, namely 2-methyl-8-fluorotryptanthrin 3;

[0063] Step (3): S...

Embodiment 3

[0067] Step (1): Synthesis of 5-methylisatoic anhydride

[0068]

[0069] Please refer to the above formula, suspend 1000.0mg (6.213mmol) of 5-methylisatin 1 in 20mL of dry dichloromethane, add 1261.4mg (6.213mmol) of m-chloroperoxybenzoic acid at 5°C, and Stirred under 4 hours; After TLC detects that the reaction is completed, the orange solid obtained by the filtration reaction is washed with (5mL x 3) ethyl acetate to obtain 5-methylisatoic anhydride 2;

[0070] Step (2): Synthesis of 2-methyl-8-fluorotryptanthrin

[0071]

[0072] Please refer to the above formula, suspend 1000.0mg (5.650mmol) of 5-methylisatoic anhydride 2 and 1865.8mg (11.30mmol) of 5-fluoroisatin in 10mL of dry acetonitrile solvent, add 2.35mL of triethylamine , heated and stirred at 82°C to 90°C for 4 to 4.5 hours, cooled to room temperature, filtered, and the filter cake was washed with (5mL×3) methanol to obtain a yellow-green solid, namely 2-methyl-8-fluorotryptanthrin 3;

[0073] Step (3): ...

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Abstract

The invention discloses a method for improving water solubility of tryptanthrin (TRYP). The method is characterized by modifying the tryptanthrin under the condition of not changing active groups of the tryptanthrin; modifying the tryptanthrin by adopting benzyl halide of the tryptanthrin as an intermediate. The invention further discloses a method for synthesizing a mono-bromo-tryptanthrin derivative, an N-benzyl-cyclo-N-tryptamine alkanate derivative, as well as a preparation method and application of the N-benzyl-cyclo-N-tryptamine alkanate derivative. The N-benzyl-cyclo-N-tryptamine alkanate derivative disclosed by the invention has superior indoleamine-2,3-dioxygenase (IDO) inhibitor activity, has wide application prospect, and can be applied to treatment of diseases, such as cancer,alzheimer disease, depressive disorder and cataract, having the pathological features of IDO-mediated tryptophan metabolic pathways. According to the method for improving water solubility of the tryptanthrin, the water solubility of the tryptanthrin is improved greatly under the condition of not changing the active groups of the tryptanthrin. The method for improving water solubility of the tryptanthrin, disclosed by the invention, has the advantages of easy operation, mild condition and the like, and is easy for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a method for synthesizing monobromotryptanthrin, N-benzylcyclo-N-alkanoic acid tryptanthrin derivatives and a preparation method and application thereof. Background technique [0002] Indoleamine-2,3-dioxygenase (IDO) is the only rate-limiting enzyme other than the liver that can mediate the degradation of human tryptophan along the kynurenine pathway. When IDO is overactive, the content of tryptophan in the local environment decreases significantly, making the proliferation of T cells stagnate at G 1 Expect. Moreover, the metabolites of tryptophan, uridine and quinolinic acid, also have a direct killing effect on T cells. Many studies have found that IDO is closely related to the pathogenesis of various diseases, and it has been confirmed as the target of major diseases such as cancer, Alzheimer's disease, cataract and depression. Therefore, the study of IDO inhibit...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P35/00A61P25/28A61P25/24A61P27/12
CPCC07D487/04A61P35/00A61P25/28A61P25/24A61P27/12
Inventor 匡春香李缘圆
Owner TONGJI UNIV
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