Compound for inducing expression of anti-aging gene KLOTHO and application thereof

A compound and alkyl technology, applied in the field of expressed compounds, can solve problems such as the reduction of klothomRNA expression, achieve excellent effects, prevent skin aging, and inhibit cell aging

Pending Publication Date: 2022-05-13
KLOTHO SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The expression of Klotho mRNA in kidney tissue was significantly higher than that in other tissues, but the expression of klotho

Method used

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  • Compound for inducing expression of anti-aging gene KLOTHO and application thereof
  • Compound for inducing expression of anti-aging gene KLOTHO and application thereof
  • Compound for inducing expression of anti-aging gene KLOTHO and application thereof

Examples

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preparation example Construction

[0141] The present invention provides the preparation method of the compound represented by chemical formula 1A, it is as following reaction formula 1, comprises the following steps:

[0142] Step 1, after dissolving compound 2 in an organic solvent, adding compound 3, reacting at a temperature of 10°C to 50°C for 12 hours to 20 hours to obtain compound 4; and

[0143] Step 2, add dropwise the organic solvent in which compound 4 obtained in the above step 1 is dissolved in the organic solvent in which potassium superoxide is dissolved, and react at a temperature of 15°C to 30°C for 10 hours to 16 hours to obtain compound 1A .

[0144] Reaction 1:

[0145]

[0146] In the above reaction formula 1,

[0147] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 As defined in the chemical formula 1 of claim 1,

[0148] The above compound 1A is contained in the chemical formula 1 of claim 1 .

[0149] In the preparation method of the present invention, as examples of the above-ment...

Embodiment 1

[0233] Example 1: N-(Benzo[d]oxazol-2-yl)-2-chloro-4-nitrobenzamide (N-(Benzo[d]oxazol-2-yl)-2-chloro- 4-nitrobenzamide, FCCS-17064) preparation

[0234]

[0235] Step 1: Dimethyl(2-chloro-4-nitrobenzoyl)iminodithiocarbonate (Dimethyl(2- Preparation of chloro-4-nitrobenzoyl)carbonimidodithioate, 17064-2-1)

[0236] 2-Chloro-4-nitrobenzamide (2-Chloro-4-nitrobenzamide) (500mg, 2.49mmol), carbon disulfide (Carbon disulfide, CS 2 ) (759mg, 9.97mmol), iodomethane (1.13g, 7.97mmol) were dissolved in dimethylformamide (N,N-dimethylformamide) (7mL), and 60% sodium hydride (200mg, 4.98mmol) was added, and Stir at room temperature for 5 hours.

[0237] Ice-cold water was slowly added to the reaction mixture and ethylacetate was extracted. The organic layer was washed with brine, and Na 2 SO 4 After drying, the solvent was removed under reduced pressure. Purification of the reaction mixture by Silica-gel column chromatrography (10% Ethyl acetate / n-hexane) afforded dimethyl(2-...

Embodiment 2

[0243] Example 2: 8-Methyl-2-[N-(3,4-dichlorophenyl)]aminobenzoxazole (8-Methyl-2-[N-(3,4-dichlorophenyl)]aminobenzoxazole, FCCS-17065) Preparation

[0244]

[0245] Step 1: 1-(3,4-dichlorophenyl)-3-(2-hydroxy-5-methylphenyl)thiourea (1-(3,4- Preparation of Dichlorophenyl)-3-(2-hydroxy-5-methylphenyl)thiourea, 17065-2-1)

[0246] After dissolving 2-amino-p-cresol (2-Amino-p-cresol) (300mg, 2.44mmol) in methanol (methanol) (12mL), add 3,4-dichlorophenylisothiocyanate ( 3,4-dichlolrophenyl isothiocyanate) (497 mg, 2.44 mmol) and stirred at room temperature for 18 hours. After confirming the completion of the reaction by thin layer chromatography (thin layer chromatography, TLC), it was cooled in a refrigerator (0° C. to 4° C.). The precipitated solid was filtered to obtain 1-(3,4-dichlorophenyl)-3-(2-hydroxy-5-methylphenyl)thiourea as a white solid (346 mg), which was used directly in next step.

[0247] 1 H NMR (400MHz, acetone-d 6 ); J = 8.4Hz) 2.24(s, 3H).

[0...

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Abstract

The present invention relates to a compound for inducing the expression of an anti-aging gene klotho, and a method for preparing the same, the compound represented by chemical formula 1 of the present invention having an excellent effect of increasing the expression level of a Klotho gene, which is an aging-related gene. Thus, the compound can be used as a pharmaceutical composition, a cosmetic composition or a food composition for preventing skin aging, inhibiting cell aging, or preventing, treating, or ameliorating diseases induced by vascular aging or kidney diseases.

Description

technical field [0001] The present invention relates to a compound for inducing expression of anti-aging gene klotho and use thereof. Background technique [0002] In the senescence-accelerated mice (SAM) reported in 1981, it was known that there may be genes capable of regulating the aging of animals. During the mating of rats of the AKR / J series, the rats produced by chance aged more rapidly than rats of the same series, and it was confirmed that the rats had multiple genetic variations. Subsequently, a group of genes associated with aging was reported in the 1990s. The reporter gene belongs to the RecQ family (RecQ family), a gene expressed called DNA helicase (helicase). Mutations in this gene have been reported to cause premature aging or cancer, which is known to affect DNA repair. The single gene associated with aging is the klotho gene reported in 1997. The Klotho gene was discovered by accident when making a transformed animal model of hypertensive rats. In rats...

Claims

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Application Information

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IPC IPC(8): C07D263/58C07D263/60A61K31/423A23L33/10A61K8/49A61P13/12A61P17/18A61P9/14A61P9/12A61P9/00A61P9/10A61P13/08A61P7/02A61Q19/08
CPCC07D263/58C07D263/60A61K8/49A61P13/12A61P17/18A61P9/14A61P9/12A61P9/00A61P9/10A61P13/08A61P7/02A61Q19/08A23L33/10A23V2002/00A23V2200/30A23V2200/318A61K31/42
Inventor 郑东柱
Owner KLOTHO SCI
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