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Charles ketone oxime and its composition , preparation method and uses

A composition and technology of dimethyl chalcone are applied in the directions of oxime preparation, drug combination, amine active ingredients, etc., which can solve the problems of poor solubility and low oral bioavailability of chalcone, and achieve good solubility. Effect

Inactive Publication Date: 2006-07-26
SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, natural chalcones are generally poorly soluble, difficult to administer by injection, and have low oral bioavailability

Method used

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  • Charles ketone oxime and its composition , preparation method and uses
  • Charles ketone oxime and its composition , preparation method and uses
  • Charles ketone oxime and its composition , preparation method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: the preparation of the compound of formula (1)

[0021] Take 100mg of 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone and 100mg of hydroxylamine hydrochloride, add 7mL of pyridine to dissolve, heat and reflux for 2 hours, pour the reaction solution into In 50mL of 1mol / L hydrochloric acid aqueous solution, filter to collect the precipitate, dissolve it with ethyl acetate, transfer the ethyl acetate solution into a separating funnel, wash with water three times, concentrate under reduced pressure to dryness, put on a silica gel column, and dissolve with petroleum ether-acetone (Volume ratio 6:1) was eluted and isolated to obtain the product.

Embodiment 2

[0022] Embodiment 2: the identification of embodiment 1 product

[0023] Yellow powdery solid. Positive ion HRTOFMS (m / z): 314.1398[C 18 h 19 NO 4 +H] + (calculated value: 314.1392). Positive ion ESIMS: 352[M+K] + , 336[M+Na] + , 314[M+H] + , 296[M-H 2 O+H] + , 280, 220, 208, 193, 103. 1 H NMR (400MHz, acetone-d 6 ): 7.42 (2H, d, J = 8.0Hz, H-2 and H-6), 7.30 (2H, t, J = 8.0Hz, H-3 and H-5), 7.22 (1H, t, J = 8.0Hz, H-4), 7.05(1H, d, J=16Hz, H-β), 6.41(1H, d, J=16Hz, H-α), 3.53(3H, s, OCH3), 2.11(3H ,s,CH 3 ), 2.09 (3H, s, CH 3 ); 13 C NMR (100MHz, acetone-d 6 ): 155.8(C×2), 155.1(C), 151.2(C), 137.6(C), 134.6(CH), 129.4(CH×2), 128.8(CH), 127.5(CH×2), 127.0( CH), 110.0(C), 108.4(C), 107.0(C), 61.0(OCH 3 ), 9.3 (CH 3 ), 9.2 (CH 3 ). By analysis, it is confirmed that the product obtained in Example 1 is a compound of formula (1), i.e. 2′, 4′-dihydroxy-6′-methoxyl group-3′, 5′-dimethylchalcone oxime (DMDO ).

Embodiment 3

[0024] Example 3: Inhibitory Effect of DMDO on Phosphorylation of Receptor Tyrosine Kinases

[0025] Take ECV304 (VEGFR2 or KDR), MDA-MB-453 (HER2), C6 (PDGFR) cells in the logarithmic growth phase, and make 5×10 5 / mL, then add it to a 12-well plate, add 1mL to each well. On the second day, the culture solution was aspirated, and serum-free culture solution was added, and then different concentrations of DMDO were added for treatment for 30 minutes, and anti-KDR, anti-HER2, and anti-PDGFR antibodies were used for immunoprecipitation, and then anti-phosphotyrosine Antibody Western blot was used to detect the phosphorylation levels of KDR, HER2 and PDGFR. see attached results Figure 1~3 .

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Abstract

The related chalketoxime shown as the formula (1) is prepared by heating and reflux reacting the 2', 4'-dihydroxy -6'-methoxyl-3', 5'-dimethylchalcone and hydroxylamine hydrochloride in pyridine, which has well solvability, fit to direct inject for drug, restrains obviously all of the activity of blood vessel endothelium growth factor receptor, HER2 receptor and Tyr kinase as PDGFR receptor, the external growth of cells for breast cancer and liver cancer, and the phosphorylation of KDR in ECV304 cell, HER2 in MDA-MB-453 cell and PDGFR receptor in C6 cell, and benefit to treat tumor.

Description

technical field [0001] The present invention relates to a chalcone oxime, specifically to 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone oxime, and to a preparation method thereof , a composition using it as an active ingredient and its application in medicine for treating tumors. Background technique [0002] Malignant tumor is a common disease that seriously endangers human health and has become the second cause of death after cerebrovascular disease. Cytotoxic tumor chemotherapy drugs have been developed for decades, and the treatment of tumors has approached or reached a plateau, and new therapeutic drugs or methods are urgently needed. [0003] There are abnormalities in signal transduction pathways in many tumors, such as vascular endothelial growth factor receptor (VEGFR), which plays an important role in the occurrence and development of various tumors, and the overexpression of EGFR family receptors is common in epithelial cell tumors , Amplification and overex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/48C07C249/08A61K31/15A61P35/00
Inventor 魏孝义张凤仙朱孝峰
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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