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Fluorescent retinoid x receptor binding molecules and uses thereof

A receptor binding and binding technology, which is applied in the direction of organic active ingredients, medical preparations containing active ingredients, active ingredients of heterocyclic compounds, etc., can solve the problems of inability to study agonism or antagonism, increased RXR amount, and shorter working time long wait question

Active Publication Date: 2021-05-04
UNIV OKAYAMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the method described in Non-Patent Document 7, unless two types of coactivators and corepressors having fluorophores are used, it is impossible to study the agonism or antagonism of the substance to be evaluated against RXR
Therefore, there is a problem that the amount of RXR used in the experiment increases and the work time becomes longer.

Method used

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  • Fluorescent retinoid x receptor binding molecules and uses thereof
  • Fluorescent retinoid x receptor binding molecules and uses thereof
  • Fluorescent retinoid x receptor binding molecules and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] [Example 1] Synthesis of target compound 10

[0105] The synthesis scheme of the target compound 10 in this example is shown in the following formula.

[0106]

[0107] 1) Synthesis of compound 2

[0108] 2,4-Dihydroxybenzaldehyde (3.3 g, 24 mmol) was dissolved in acetic acid (24 mL), and bromine (1.2 g, 24 mmol) was added dropwise over 10 minutes, followed by stirring at room temperature for 20 hours. Thereafter, it was confirmed that the reaction was complete using a TLC (Thin Layer Chromatography) plate (ethyl acetate:n-hexane=1:3, developed twice). Water (35 mL) was added, and the precipitated solid was collected by filtration and washed with water to obtain crude crystals (5.3 g). Flash column chromatography (ethyl acetate:n-hexane=1:4→1:3), followed by recrystallization (ethyl acetate:n-hexane), gave light brown needle-like crystals of 2 (1.5g, 28%) .

[0109] 1 H NMR (300MHz, CDCl 3 )δ11.25(s,1H),9.70(d,1H,J=0.5Hz),7.66(s,1H),6.63(s,1H),6.11(s,1H)

[01...

Embodiment 2

[0133] [Example 2] Synthesis of target compound 23a-c

[0134] The synthetic schemes of the target compounds 23a-c in this example are shown below.

[0135]

[0136] 1) Synthesis of compound 18

[0137]2,5-Dimethyl-2,5-hexanediol (2.0 g, 14 mmol) was dissolved in concentrated hydrochloric acid (20 mL), and stirred at room temperature for 14 hours. The solid was collected by filtration, washed with water, dissolved in dichloromethane (150 mL), and washed with water (50 mL). After drying the organic layer with magnesium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product (2.4 g) of a white solid. The obtained crude product and 2-bromophenol (2.1 mL, 20 mmol) were dissolved in anhydrous dichloromethane (30 mL), aluminum trichloride (170 mg) was added, and the mixture was stirred at room temperature under an argon atmosphere for 3 hours. The completion of the reaction was confirmed by a TLC plate (ethyl acetate:n-hexane=1:10), the reaction...

Embodiment 3

[0179] [Example 3] Synthesis of target compound 30

[0180] The synthesis scheme of the target compound 30 in this example is shown in the following formula.

[0181]

[0182] 1) Synthesis of Compound 25

[0183] Thymol (150 mg, 1.0 mmol) was dissolved in methanol (4 mL), silver sulfate (370 mg, 1.2 mmol) and iodine (300 mg, 1.2 mmol) were added, and the mixture was stirred at room temperature for 6 hours. Use (ethyl acetate:n-hexane=1:10) to confirm the completion of the reaction, pour the reaction solution into saturated sodium thiosulfate water (30 mL), filter with celite, and extract with ethyl acetate (30 mL×3). The organic layer was washed with water (40 mL×2) and saturated brine (40 mL). The obtained organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product (270 mg) of a yellow solid. Flash column chromatography (ethyl acetate:n-hexane=1:50→1:30) gave 25 (230 mg, 85%) as a yellow solid.

[0...

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PUM

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Abstract

By using a fluorescent retinoid X receptor-binding molecule represented by any one of the following formulas (1) to (3), an evaluation test for binding to RXR can be easily performed. [where, R 1 is methyl, alkoxy or styryl; R 2 Is hydroxyl, alkoxy or alkylamino; A is N or CH; B is NH or O; R 3 Is isopropyl or tert-butyl; R 4 For isopropyl or isobutyl. ]

Description

technical field [0001] The present invention relates to a fluorescent retinoid X receptor-binding molecule. It also relates to a test method for evaluating the binding ability of an evaluation substance to a retinoid X receptor using the binding molecule, a test kit for evaluating the binding ability and function of an evaluation substance comprising the binding molecule, and a test kit comprising the binding molecule. A pharmaceutical composition comprising a binding molecule as an active ingredient. Background technique [0002] Rexinoid is a collective term for substances that exhibit binding properties to retinoid X receptors (retinoid X receptor: RXR). That is, rexinoid is a retinoid X receptor-binding molecule (ligand for retinoid X receptor). [0003] Bexarotene (targretin (registered trademark)), one of the rexinoids, is an activator (agonist) of RXR and is clinically used in the United States for skin infiltrating T-cell lymphoma (CTCL) (Patent Document 1). In ad...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/80A61K31/352A61K31/44A61K31/4433A61K31/4704A61K31/4709A61P3/00A61P3/10A61P7/00A61P25/16A61P25/28A61P35/00A61P43/00C07D215/54C07D311/16C07D401/12C07D405/12G01N33/15G01N33/50
CPCA61K31/352A61K31/4433A61K31/4704A61K31/4709A61K31/498A61P3/00A61P3/10A61P7/00A61P25/16A61P25/28A61P35/00A61P43/00C07D213/80C07D215/54C07D311/16C07D401/12C07D405/12G01N33/533G01N33/582G01N33/6875
Inventor 加来田博贵山田翔也渡边将贵
Owner UNIV OKAYAMA
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