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Vitamin K3 derivatives serving as IDO inhibitor

A technology of derivatives and vitamins, which is applied in the field of synthesis of drugs and intermediates, can solve the problems of lack of high yield and achieve the effects of solvent saving, mild reaction conditions and short reaction time

Inactive Publication Date: 2010-09-15
CONJOIN PHARM SUZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are very few literatures on the synthesis of vitamin K3 derivatives, and there is a lack of high-yield, simple-to-operate synthetic literature reports

Method used

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  • Vitamin K3 derivatives serving as IDO inhibitor
  • Vitamin K3 derivatives serving as IDO inhibitor
  • Vitamin K3 derivatives serving as IDO inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the preparation of compound I

[0037]

[0038] Add 4mL dimethylformamide (DMF) to a 50mL dry round-bottomed flask, add 18mg (0.1mmol) of p-bromophenol and 42mg (0.3mmol) of anhydrous potassium carbonate respectively, track and monitor the generation of potassium salt by TLC, magnetic After stirring for 1 hour, after it generates potassium phenate; 24mg (0.1mmol) 2-bromo-1,4-naphthoquinone was poured into the system, and the system appeared brown. After reacting at room temperature for 3 hours, TLC tracked and monitored the progress of the reaction. Completely quench the reaction with 20 mL of water, add ethyl acetate, separate the organic layer, add saturated sodium bisulfite, and wash with saturated brine, dry with anhydrous sodium sulfate, and use ethyl acetate:petroleum ether=1 : 8 is the eluent and is separated and purified by column chromatography to obtain 40 mg of compound I with a yield of 75%.

[0039] The characterization data are as follows...

Embodiment 2

[0041] Embodiment 2: the preparation of compound II

[0042]

[0043]Add 4mL DMF to the dry round-bottomed flask of 50mL, add the anhydrous potassium carbonate of 16mg (0.15mmol) p-cresol and 62mg (0.45mmol) respectively, TLC follows and monitors potassium salt to generate, after magnetic stirring 2.5 hours, wait for its After the potassium phenate is generated; pour 24mg (0.1mmol) 2-bromo-1,4-naphthoquinone into the system, and the system turns brown. After reacting at room temperature for 4 hours, TLC tracked and monitored the reaction to complete, and quenched it with 20mL of water For post-reaction treatment, add ethyl acetate, separate the organic layer, then add saturated sodium bisulfite and saturated brine to wash, dry over anhydrous sodium sulfate, and use ethyl acetate:petroleum ether=1:8 as the eluent for column After separation and purification by chromatography, 30 mg of compound II was obtained, with a yield of 70%.

[0044] The characterization data are as f...

Embodiment 3

[0046] Embodiment 3: the preparation of compound III

[0047]

[0048] Add 4mL DMF to a 50mL dry round-bottom flask, add 14mg (0.15mmol) of phenol and 62mg (0.45mmol) of anhydrous potassium carbonate respectively, track and monitor the generation of potassium salt by TLC, and wait for it to generate phenol after 1 hour of magnetic stirring. After the potassium salt; 24mg (0.1mmol) 2-bromo-1,4-naphthoquinone was poured into the system, and the system showed a reddish-brown color. After 1.5 hours of reaction at room temperature, the TLC tracking monitoring reaction was completed, and the reaction was quenched with 20mL of water. After treatment, add ethyl acetate, separate the organic layer, then add saturated sodium bisulfite and saturated brine to wash, dry over anhydrous sodium sulfate, and use ethyl acetate:petroleum ether=1:7 as eluent for column layer 24 mg of compound III was obtained through separation and purification, with a yield of 81%.

[0049] The characterizat...

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Abstract

The invention belongs to the technical fields of medicaments and intermediate synthesis, and in particular relates to vitamin K3 derivatives and a preparation method thereof. The 1,4-naphthoquinone derivatives are conveniently synthesized by using 2-bromine-1,4-naphthoquinone as raw materials through one-step reaction. The vitamin K3 derivatives synthesized by the method contain vitamin K3 structures and can be used as medicaments and important synthesized intermediates. The method for preparing the vitamin K3 derivatives has the characteristics of simple operation, mild condition, low cost, high yield, and the like, has wide application prospect, and is easy for industrialized production. An IDO inhibitor synthesized by the method and containing the vitamin K3 structure can be applied to the treatment of diseases with IDO-mediated tryptophan metabolic pathway pathologic features, wherein the diseases at least comprise tumor diseases, cancers, Alzheimer, autoimmune diseases, cataracts, mood disorders, depression, and anxiety disorder.

Description

technical field [0001] The invention belongs to the technical field of medicine and intermediate synthesis, and in particular relates to a vitamin K3 derivative and an IDO inhibitor thereof. Background technique [0002] Indoleamine 2,3-dioxygenase (Indoleamine 2,3-dioxygenase, IDO) is widely distributed in many tissues and cells of humans and animals, and is the only enzyme that catalyzes the decomposition of tryptophan along the kynurenine pathway outside the liver metabolic rate-limiting enzyme [1] . IDO is expressed at low levels under normal conditions and significantly increased under inflammatory or infectious conditions [2] . IDO is closely related to the pathogenesis of many diseases, and has been proven to be the target of cancer, Alzheimer's disease, depression, cataract and other major diseases [3-9] . Therefore, IDO inhibitors are very potential drugs, and finding highly active IDO inhibitors has important theoretical significance and application value. ...

Claims

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Application Information

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IPC IPC(8): C07C50/32C07C46/00A61K31/122A61P35/00A61P25/28A61P37/02A61P27/12A61P25/24A61P25/22A61P25/00
Inventor 匡春香杨青
Owner CONJOIN PHARM SUZHOU CO LTD
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