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Preparation method of tryptanthrin compound and new application of tryptanthrin compound in preparing indoleamine-2,3-dioxygenase (IDO) inhibitor

A compound and inhibitor technology, applied in the field of medicinal chemistry, can solve the problems of low extraction rate, difficult to meet research and clinical medication, long separation process, etc., and achieve good research and development results.

Active Publication Date: 2012-07-18
SHENYANG XINMA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although tryptanthrin can be extracted from indigo plants such as Polygonum indigo, Isatis indigo, and other indigo plants and metabolites of microorganisms, the separation process is long and the extraction rate is low, which is difficult to meet the needs of research and clinical medicine.

Method used

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  • Preparation method of tryptanthrin compound and new application of tryptanthrin compound in preparing indoleamine-2,3-dioxygenase (IDO) inhibitor
  • Preparation method of tryptanthrin compound and new application of tryptanthrin compound in preparing indoleamine-2,3-dioxygenase (IDO) inhibitor
  • Preparation method of tryptanthrin compound and new application of tryptanthrin compound in preparing indoleamine-2,3-dioxygenase (IDO) inhibitor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of tryptanthrin (formula I)

[0024]

[0025] Add 3mL toluene, 163mg (1mmol) isatoic anhydride (purchased from Shanghai Kangtuo Chemical Co., Ltd.), 147mg (1mmol) isatin (purchased from Aladdin Reagent Co., Ltd.), 505mg (5mmol) to a 25mL dry round bottom flask ) triethylamine, then heated up to 110°C, refluxed and stirred for 3-4h, after TLC detection showed that the reaction was complete, the solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol to obtain 228 mg of compound of formula I with a yield of 92%.

[0026] The characterization data are as follows: 1 H-NMR (400MHz, CDCl 3 )δ=8.64(d, 1H), 8.45(d, 1H), 8.04(d, 1H), 7.92(d, 1H), 7.88(t, 1H), 7.80(t, 1H), 7.69(t, 1H ), 7.44(t, 1H).

Embodiment 2

[0027] Embodiment 2: the preparation of 8-methyl tryptanthrin (formula II)

[0028]

[0029] Add 3 mL of toluene, 163 mg (1 mmol) isatoic anhydride, 161 mg (1 mmol) 5-methyl isatin (purchased from Qingdao Hexing Fine Chemical Co., Ltd.), 505 mg (5 mmol) triethylamine into a 25 mL dry round bottom flask , and then heated up to 110° C., refluxed and stirred for 3-4 hours. TLC showed that after the reaction was complete, the solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol to obtain 235 mg of the compound of formula II with a yield of 90%.

[0030] The characterization data are as follows: 1 H-NMR (400MHz, CDCl 3 )δ=8.49(d, 1H), 8.43(d, 1H), 8.02(d, 1H), 7.84(t, 1H), 7.67(m, 2H), 7.59(d, 1H), 2.46(s, 3H ).

Embodiment 3

[0031] Embodiment 3: the preparation of 8-fluorotryptanthin (formula III)

[0032]

[0033] Add 3 mL of toluene, 163 mg (1 mmol) isatoic anhydride, 165 mg (1 mmol) 5-fluoroisatin (see step (2) of Example 5 for its preparation method, 505 mg (5 mmol) three Ethylamine, then warmed up to 110°C, refluxed and stirred for 3-4 hours, TLC showed that after the reaction was completed, the solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol to obtain 242 mg of compound of formula III, with a yield of 91%.

[0034] The characterization data are as follows: 1 H-NMR (400MHz, CDCl 3 )δ=8.64(m, 1H), 8.44(d, 1H), 8.03(d, 1H), 7.87(t, 1H), 7.70(t, 1H), 7.58(m, 1H), 7.49(m, 1H ).

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Abstract

The invention relates to a preparation method of tryptanthrin compound and a new application of tryptanthrin compound in preparing indoleamine-2,3-dioxygenase (IDO) inhibitor, in particular to an application of tryptanthrin compound in preparing IDO inhibitor and in preparing medicine for preventing and / or treating diseases having pathological characteristics of tryptophan metabolic disturbance mediated by IDO. The structure of the tryptanthrin compound is shown in formula A in the description, wherein R1 and R2 are respectively and independently selected from hydrogen, nitryl, C1 to C5 alkyl, halogen or piperazinyl. The tryptanthrin compound can be used as an IDO inhibitor with high activity and is used for treating diseases having pathological characteristics of tryptophan metabolic disturbance mediated by IDO such as tumor, cancer, Alzheimer disease, autoimmune disease, cataract, mental block, tristimania, anxiety neurosis, acquired immure deficiency syndrome (AIDS) and other serious diseases, and as a medicinal resource which is very difficult to get, the tryptanthrin compound has good potential on researching and developing new medicine.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of tryptanthrin compounds and their new application in preparing IDO inhibitors. Background technique [0002] Indoleamine 2,3-dioxygenase (Indoleamine 2,3-dioxygenase, IDO) is an enzyme containing heme in cells, and it is the only one outside the liver that can catalyze the metabolism of tryptophan to make it along the path of kynurenine The rate-limiting enzyme of the acid pathway breaks down to a series of metabolites including quinolinic acid (MacKenzie, C. R. et. al. Current Drug Metabolism, 2007, 8: 237-244.). Since the 1990s, indoleamine 2,3-dioxygenase (IDO) and its kynurenine pathway (Kynurenine pathway, KP), which catalyzes tryptophan metabolism, have been The important role it plays in various disease processes is attracting increasing attention. [0003] IDO is related to many physiological and pathological processes. Studies on p...

Claims

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Application Information

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IPC IPC(8): A61K31/519A61P35/00A61P25/28A61P37/02A61P27/12A61P25/00A61P25/24A61P25/22A61P31/18A61P35/02
Inventor 匡春香王勇王淑君陈斌关玉晶刘莹田宁
Owner SHENYANG XINMA PHARMA
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