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Dibenzo iodonium salts and anticancer application thereof

A technology of dibenzoiodonium salt and benzoiodonium salt, which is applied in the field of iodonium salt, and can solve problems such as easy drug resistance, lack of effective cancer treatment methods, and large side effects

Active Publication Date: 2013-06-26
SUN YAT SEN UNIV CANCER CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Over the years, although the scientific community has made great progress in the research on the mechanism of cancer formation and development, effective treatments for cancer are still relatively lacking so far.
At present, almost all antineoplastic drugs in the domestic and foreign markets generally have the disadvantages of slow onset of action, large side effects, and easy drug resistance, so their clinical use is limited to a certain extent.

Method used

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  • Dibenzo iodonium salts and anticancer application thereof
  • Dibenzo iodonium salts and anticancer application thereof
  • Dibenzo iodonium salts and anticancer application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1, the synthesis of 3-methyl-7-nitrodibenzo[b, d]-5-iodonium methylbenzenesulfonate 1:

[0048]

[0049] 4'-Methyl-4-nitro-[1,1'-biphenyl]-2-amine (1b): To a solution of p-methylphenylboronic acid (226 mg, 1.66 mmol) in ethanol (10 mL) was added 2- Bromo-5-nitroaniline (300 mg, 1.38 mmol), K 3 PO 4 (734 mg, 3.4 6 mmol), Pd(PPh 3 ) 4 (80 mg, 69.12 umol). The reaction solution was heated to reflux for 6 hours under the protection of argon, and then the ethanol was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 20 / 1-10 / 1) to obtain 1b as a yellow solid (236 mg, 75% yield). 1 H NMR (400 MHz, DMSO) δ 7.61 (d, J = 2.4 Hz, 1H), 7.41 (d, J = 2.4 Hz, 1H), 7.32 (q, J = 8.2 H...

Embodiment 2

[0052] Example 2, Synthesis of 3-fluoro-7-nitrodibenzo[b,d]-5-iodonium trifluoromethanesulfonate (2):

[0053]

[0054] 4'-Fluoro-4-nitro-[1,1'-biphenyl]-2-amine (2b): To a solution of p-fluorophenylboronic acid (524 mg, 3.87 mmol) in ethanol (15 mL) was added 2-bromo -5-Nitroaniline (700 mg, 3.23 mmol), K 3 PO 4 (1.71 g, 8.06 mmol), Pd(PPh 3 ) 4 (186.36 mg, 161.28 umol). The reaction solution was heated to reflux for 6 hours under the protection of argon, and then the ethanol was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 20 / 1-10 / 1) to obtain 2b as a yellow solid (676 mg, 90% yield).

[0055] 2-iodo-4'-fluoro-4-nitro-1,1'-biphenyl (2a): Add 4M aqueous hydrochloric acid (7.28 mL) to 2b (67...

Embodiment 3

[0057] Example 3, the synthesis of compound 3-nitrodibenzo[b,d]-5-iodonium trifluoromethanesulfonate (3):

[0058]

[0059] 4-Nitro-[1,1'-biphenyl]-2-amine (3b): To a solution of phenylboronic acid (300 mg, 2.46 mmol) in ethanol (5 mL) was added 2-bromo-5-nitroaniline ( 640.76 mg, 2.95 mmol), K 3PO 4 (1.31 g, 6.15 mmol), Pd(PPh 3 ) 4 (142.16 mg, 123.02 umol). The reaction solution was heated to reflux for 6 hours under the protection of argon, and then the ethanol was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent petroleum ether: ethyl acetate = 20 / 1-10 / 1) to obtain yellow liquid 3b (515 mg, 98% yield).

[0060] 2-Iodo-4-nitro-1, 1'-biphenyl (3a): To 3b (515 mg, 2.40 mmol) in tetrahydrofuran (10 mL) was added 4M aqueous hydroc...

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Abstract

The invention relates to dibenzo iodonium salts represented by the following structural formula (I), and discloses a preparation method and an application thereof. In in-vitro experiments, the iodonium salts substantially inhibit the growths of cells of human-sourced pancreatic cancer, stomach cancer, colon cancer and other malignant tumors, and provide substantially killing effects against cells of ovarian cancer, lung cancer, liver cancer, leukemia, glioma, bone marrow cancer and other malignant tumors. In animal experiments, with the salts, the growths of human pancreatic cancer and colon cancer xenografts in nude mice can be substantially inhibited. The compounds can be used in developing novel antitumor medicines. (I) is shown below.

Description

technical field [0001] The present invention relates to iodonium salts, more particularly, to a dibenzoiodonium salt and its analogous compounds and their anticancer application. Background technique [0002] Cancer seriously affects human life and health around the world, and it has replaced cardiovascular disease as the number one disease that causes human death in the world. Over the years, although the scientific community has made great progress in the research on the mechanism of cancer formation and development, effective treatments for cancer are still relatively lacking so far. At present, almost all antineoplastic drugs in the domestic and foreign markets generally have the disadvantages of slow onset of action, large side effects, and easy drug resistance, so their clinical use is limited to a certain extent. Finding new anti-cancer targets and developing highly effective and low-toxic anti-cancer drugs targeting these new targets are currently important scient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D347/00A61K31/33A61P35/00
Inventor 文石军黄蓬朱大潜黎小兵
Owner SUN YAT SEN UNIV CANCER CENT
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