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Aromatic iodonium salts as NADH oxidase inhibitors and anti-tumor application thereof

A nicotinamide adenine and oxidase inhibitor technology is applied to the reduced nicotinamide adenine dinucleotide oxidase inhibitor aromatic iodonium salt and its anti-tumor application field, which can solve the problem of slow onset of anti-tumor drugs, slow onset of anti-tumor drugs, Easy to produce drug resistance, clinical use restrictions and other problems

Inactive Publication Date: 2012-08-01
文石军 +2
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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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  • Aromatic iodonium salts as NADH oxidase inhibitors and anti-tumor application thereof
  • Aromatic iodonium salts as NADH oxidase inhibitors and anti-tumor application thereof
  • Aromatic iodonium salts as NADH oxidase inhibitors and anti-tumor application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1, Synthesis of Compound 1:

[0033]

[0034] In an ice-water bath, slowly add the acetic acid solution (1.5mL) of raw material 1-a (50mg, 0.16mmol) to the mixed solution of potassium disulfate (52mg, 0.19mmol) in concentrated sulfuric acid (1mL) and acetic acid (1.5mL). ). After the addition was completed, the reaction solution was stirred under an ice bath for 30 minutes, and then stirred at room temperature for 3 hours. After the completion of the reaction, the reaction solution was poured into an aqueous sodium chloride solution with crushed ice, and the white precipitate obtained was collected by filtration, washed with ice water three times, and dried in vacuo to obtain compound 1 (25 mg, 45%). 1 HNMR (400MHz,) δ 8.54 (d, J = 8.2 Hz, 1H), 8.47 (d, J = 8.0 Hz, 1H), 8.39 (d, J = 9.0 Hz, 1H), 7.96 (d, J = 2.5 Hz, 1H), 7.77 (t, J=7.6 Hz, 1H), 7.58 (t, J=7.7 Hz, 1H), 7.22-7.15 (m, 1H), 3.91 (s, 3H). MS(ESI, m / z)309.0(M + ).

Embodiment 2

[0035] Example 2: Synthesis of Compound 2:

[0036]

[0037] To a dichloromethane solution (4 mL) of 1a-1 (50 mg, 0.16 mmol) was added m-chloroperoxybenzoic acid (75%, 45 mg, 0.19 mmol) and trifluoromethanesulfonic acid (43 uL). After stirring for 1 hour, the reaction solution was concentrated, and then ether (1 mL) was added. After 10 minutes, the precipitated solid was collected by filtration and dried to obtain solid compound 2 (45 mg, 61%). 1 H NMR (400MHz, d6-DMSO) δ 8.56 (d, J = 6.8 Hz, 1H), 8.21 (d, J = 7.7 Hz, 1H), 8.05 (s, 2H), 7.86 (s, 1H), 7.71 (s, 1H), 7.33 (d, J=8.8 Hz, 1H), 3.95 (s, 3H). 13 C NMR (100MHz, d6-DMSO) δ 161.7, 143.3, 141.5, 131.2, 130.6, 127.4, 121.8, 118.4, 111.6, 110.5, 56.2. MS(ESI, m / z)308.9(M + ).

Embodiment 3

[0038] Example 3 Synthesis of Compound 3:

[0039]

[0040] 3 was prepared according to the synthetic strategy of compound 2. 1 H NMR (400MHz, d6-DMSO) δ8.55 (dd, J=7.9, 1.1Hz, 1H), 8.23 ​​(d, J=8.2Hz, 1H), 8.06 (dd, J=14.8, 5.9Hz, 2H) , 7.89-7.81 (m, 1H), 7.73-7.67 (m, 1H), 7.50 (d, J = 8.0 Hz, 2H), 7.32 (dd, J = 9.1, 2.8 Hz, 1H), 7.12 (d, J = 7.8 Hz, 2H), 3.95 (s, 3H), 2.29 (s, 3H). 13 C NMR (100MHz, d6-DMSO) δ 161.6, 145.5, 143.3, 141.5, 137.7, 131.3, 131.0, 130.6, 128.1, 127.3, 125.5, 121.8, 118.3, 111.6, 110.5, 56.1, 20.7. MS(ESI, m / z)308.9(M + ).

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PUM

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Abstract

The invention provides a series of novel aromatic iodonium salt compounds that are used as NADH (reduced form of nicotinamide-adenine dinucleotide) oxidase inhibitors, and discovers the new anti-cancer application of the novel aromatic iodonium salt compounds and a few of other known NADH oxidase inhibitors. The iodonium salts can inhibit the activity of NADH oxidases in in-vitro assays, and can obviously inhibit the growth of malignant cells of humanized pancreatic cancer, multiple myeloma, esophageal carcinoma, intestinal cancer and the like. To aim at new anti-cancer targets, the development of novel anti-tumor drugs can be carried forward.

Description

Technical field [0001] This patent provides a novel reduced nicotinamide adenine dinucleotide oxidase inhibitor aromatic iodonium salt, and discovered that the reduced nicotinamide adenine dinucleotide oxidase inhibitor aromatic iodonium salt has obvious anti- Cancer activity. Background technique [0002] Cancer poses a serious threat to human life and health. It has replaced cardiovascular disease as the world's number one disease causing human deaths. Over the years, although the scientific community has made great progress in the research on the mechanism of cancer formation and development, effective treatment methods for cancer are still lacking so far. At present, almost all anti-tumor drugs on the domestic and foreign markets generally have shortcomings such as slow onset, large side effects, and resistance to drugs, so their clinical use has been limited. Finding new anti-cancer targets and developing high-efficiency and low-toxic anti-cancer drugs for these new target...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D347/00C07D517/04A61K31/33A61P35/00
Inventor 文石军黄蓬
Owner 文石军
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