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Pharmaceutical uses of sulfur-containing compound

a sulfur-containing compound and compound technology, applied in the field of pharmaceutical uses of sulfur-containing compounds, can solve the problems of malignancy with poor clinical outcome, harmful side effects on normal healthy cells in the human body, etc., and achieve the effects of inhibiting the activity of a factor related, significant inhibiting the functions of inflammatory proteins, and inhibiting lung cancer metastasis and/or growth

Active Publication Date: 2016-01-14
NAT SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent is about a new compound that has the ability to stop the growth and spread of tumors. This compound has been tested in the lab and has been found to inhibit the actions of inflammatory proteins related to cancer. It has also been shown to stop the growth and spread of lung cancer in animal tests. This patent aims to provide uses for this new compound and to protect methods for making it.

Problems solved by technology

Lung Cancer 2005, 7, 92-99), however, these treatments have harmful side effects on normal healthy cells in the human body.
Overgrowth, invasion, and metastasis are the major characteristics of malignancy with poor clinical outcome.

Method used

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  • Pharmaceutical uses of sulfur-containing compound
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  • Pharmaceutical uses of sulfur-containing compound

Examples

Experimental program
Comparison scheme
Effect test

preparation 1

[0059]2-Mercaptoethanol (1.80 g, 98%, 27.14 mmole) and triethylamine (0.53 mL, 3.77 mmole) were added in a round bottom flask containing 22 mL of acetone. Followed by stirring in a 0° C. ice bath, a solution of methyl vinyl ketone (2.31 mL, 27.14 mmole) in 4 mL acetone was dropped into the flask slowly. After the addition, the temperature of the reaction was raised to room temperature, and the reaction was continued for 16 hours. The solvent-free product was subject to silica gel column chromatography to afford a thioether compound represented by the following formula 26 (3.35 g, yield 100%),

[0060]Thioether compound represented by formula 26: colorless oil, IR (KBr) νmax 3405, 1713, 1416, 1362, 1161, 1045, 1010 cm−1; 1H NMR (CDCl3, 300 MHz) δH 3.73 (2H, dt, J=5.6, 5.4 Hz), 2.75 (4H, br s), 2.72 (2H, t, J=5.4 Hz), 2.46 (1H, t, J=5.6 Hz, OH) 2.17 (3H, s); 13C NMR (CDCl3, 75 MHz) δC 207.0 (qC), 60.6 (CH2), 43.7 (CH2), 35.6 (CH2), 30.2 (CH3), 25.4 (CH2); ESIMS m / z 171 [M+Na]+; HRESIMS m...

preparation 2

[0061]The thioether compound represented by formula 26 (1.00 g, 6.76 mmole) prepared as Preparation 1 and MnSO4.H2O (23 mg, 0.14 mmole) were mixed with acetonitrile (156 mL) in a 500 mL round bottom flask (Flask A) and the mixture was stirred vigorously at room temperature. The aqueous solutions of sodium hydrogen carbonate buffer (115 mL, 0.2 M, pH=8.0) and 30% hydrogen peroxide solution (3.38 mL) were charged into a 250 mL flask at 0° C. and stirred well, and then added slowly into Flask A. After reacting for 2 hours, ethyl acetate / isopropyl alcohol (3:1) was added for extraction (200 mL×6). The combined organic extract was concentrated under reduced pressure and the residue was purified over a silica gel column (eluted with hexane / EtOAc=1:3) for obtaining the compound represented by formula 3 (1.03 g, yield 84%). Compound represented by formula 3: colorless crystals, mp 59-60° C.; IR (KBr) νmax 3416, 1715, 1416, 1366, 1311, 1120, 1009 cm−1; 1H NMR (CDCl3, 300 MHz) δH 4.02 (2H, t,...

preparation 3

[0062]To a stirring solution of the thioether compound represented by formula 26 (1.00 g, 6.76 mmole) prepared as Preparation 1 in dichloromethane (64 mL) in a 125 mL round bottom flask was slowly added m-chloroperoxybenzoic acid (2.92 g, 16.90 mmole) in batches. After the addition, the reaction was monitored with TLC until the thioether compound was completely consumed. Then, dichloromethane was removed, and the resulted mixture was added with 100 mL of saturated sodium hydrogen carbonate solution and stirred vigorously. The resulted crude product was extracted with ethyl acetate (100 mL×10) and the combined extract was concentrated under reduced pressure. The obtained product was purified with a silica gel column (eluted with hexane / EtOAc=1:3) to afford the compound represented by formula 3 (1.00 g, yield 82%).

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Abstract

The invention relates to uses of the sulfur-containing compound in inhibiting activities of a factor related to cancer metastasis and / or growth. Preferably, the invention relates to uses of the sulfur-containing compound in inhibiting lung cancer metastasis and / or growth.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]The invention relates to uses of a sulfur-containing compound. Said sulfur-containing compound has ability to inhibit activities of a factor related to cancer metastasis and / or growth and to inhibit lung cancer metastasis and / or growth.[0003]2. Description of the Related Art[0004]Non-small cell lung cancer (NSCLC) is one of the main causes of cancer death, and its incidence is increasing. Surgery, radiotherapy, and chemotherapy are the major treatment methods to reduce lung cancer mortality (Saba, N. F.; Khuri, F. R. Chemoprevention strategies for patients with lung cancer in the context of screening. Clin. Lung Cancer 2005, 7, 92-99), however, these treatments have harmful side effects on normal healthy cells in the human body. Therefore, it is important to discover new agents to treat lung cancer safely without affecting the body's healthy cells. The deregulation of signaling pathways such as PI3K / Akt is often implica...

Claims

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Application Information

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IPC IPC(8): C07C317/24C07C317/28C07C317/44C07C323/22C07C323/41C07C323/52C07D295/185
CPCC07C317/24C07C323/52C07C323/41C07C317/28C07C323/22C07C317/44C07D295/185A61K31/121A61K31/19A61K31/22
Inventor WU, CHIEH-HSISHEU, JYH-HORNGCHEN, CHIH-YICHIEN, YI-CHUNGCHEN, SHUO-CHUEHPAN, CHUN-HSUHUANG, CHIUNG-YAO
Owner NAT SUN YAT SEN UNIV
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