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2,4,5-trisubstituted imidazole compounds and its preparing process and pharmaceutical use

A technology of compounds and substituents, applied in organic chemistry and other directions, can solve problems such as affecting functions

Inactive Publication Date: 2003-06-25
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, it has been reported that the compound OC144-093 has a strong reversal activity and may not be a substrate of P-pg. Its mechanism of action is mainly to bind with P-gp, thereby affecting the "drug pump" function of P-gp

Method used

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  • 2,4,5-trisubstituted imidazole compounds and its preparing process and pharmaceutical use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] 0.07g (0.3mmol) Pd(OAc) 2 , 0.37g (1.22mmol) PPh 3 Placed in 60ml of DMF, added 5g (27mmol) p-bromobenzaldehyde, 2.32g (27mmol) methyl acrylate, reacted at 100°C for 14h, separated by column chromatography to obtain a white solid product 1, weighing 4.80g, melting point 82.5°C, product The rate is 93.47%. 1 H-NMR (500MHz, CDCl 3 ): δ3.83(S, 3H), 6.56(d, 1H), 7.67(m, 2H), 7.72(d, 1H), 7.90(m, 2H), 10.04(S, 1H); MS(FAB) (m / z): 191 (base peak, M+H), 159 (M-OCH 3 ), 131 (M-COOCH 3 ), 105 (M-CH=CHCO 2 CH 3 ). Compound 1 Example 2: Synthesis of 1-(p-ethylene glycol formalyl phenyl)-trans-methyl acrylate (compound 2)

Embodiment 2

[0044] Dissolve 1.90g (10mmol) of 1 in 60ml of benzene, add 1.50g (24.2mmol) of ethylene glycol, install a water separator, reflux for 3h, cool to room temperature, add 20ml of ethyl acetate, and then use saturated NaHCO 3 , NaCl solution (each 2 × 20ml), washed with anhydrous Na 2 SO 4 After drying, the solvent was distilled off to obtain a light yellow solid, which was separated by column chromatography to obtain a white solid product 2, weighing 2.25 g, with a yield of 96.15%. 1 H-NMR (500MHz, CDCl 3 ): δ3.81(S, 3H), 4.09(m, 4H), 5.83(s, 1H), 6.46(d, 1H), 7.53(m, 4H), 7.70(d, 1H); MS(FAB) (m / z): 235(M+H), 203(M-OCH 3 ), 175 (M-COOCH 3 ), 149 (base peak, M-CH=CHCO 2 CH 3 ). Compound 2 Example 3: Synthesis of 1-(p-ethylene glycol formalyl phenyl)-trans-propenyl alcohol (compound 3)

Embodiment 3

[0045] At room temperature, add 30ml absolute anhydrous diethyl ether and 0.4gLiAlH 4 (10.54mmol) of 2.34g (10mmol) 30ml of absolute anhydrous ether solution was slowly dropped into the mixed suspension, and the drop was completed in about 20 minutes. Stir for another 60 minutes, add 10 ml of 1M NaOH aqueous solution, stir for 20 minutes, stand to separate layers, wash the ether layer with saturated NaCl solution, wash with anhydrous NaOH 2 SO 4 After drying, the solvent was distilled off to obtain a light yellow thick liquid, which was separated by column chromatography to obtain the white solid product 3, weighing 1.65 g, with a yield of 80.10%. 1 H-NMR (500MHz, CDCl 3 ): δ2.81(br, 1H), 4.09(m, 4H), 4.23(dd, 2H), 5.76(s, 1H), 6.32(dt, 1H), 6.55(d, 1H), 7.37(m, 4H); MS(FAB)(m / z): 207(M+H), 189(M-OH), 149(M-CH=CHCH 2 OH), 73 (base peak). Compound 3 Example 4: Synthesis of p-ethylene glycol formalyl phenyl-trans-allyl chloride (compound 4)

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Abstract

The present invention relates to 2,4,5-trisulbstituted imidazole compounds and their preparation process and their application in preparing medicines for reversing multiple drug resistance of tumor cell mediated by P-glucoprotein, multiple drug resistance relative protein, lung multiple drug resistance relative protein and other membrane transport proteins and restoring the sensitivity of tumor cells with multiple drug resistance to anticancer medicines.

Description

technical field [0001] The present invention relates to 2,4,5-trisubstituted imidazole compounds and their preparation methods, and the preparation of such compounds for reversing the multidrug resistance (MDR) of tumor cells and restoring the sensitivity of tumor cells to anticancer drugs the use of. technical background [0002] Tumor is the main disease that threatens human life and health, and is the second killer of human beings. The main means of treating tumors are surgery, radiotherapy and chemotherapy. Both surgery and radiotherapy cannot remove all tumor cells accurately and tend to recur after treatment, so it is a local treatment. Chemotherapy is a systemic treatment, but the main reasons for the failure of chemotherapy are: first, dose-limiting toxic and side effects. Due to the low selectivity of anticancer drugs to tumor cells, they also have a killing effect on normal tissue cells while killing tumor cells, which limi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64C07D401/06
Inventor 符立梧阮继武古练权
Owner SUN YAT SEN UNIV
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