Specific indole compound and its preparation and use in treating and preventing cancers

A technology of compounds, indoles, applied in the field of medicinal chemistry

Inactive Publication Date: 2005-05-04
JC (WUXI) CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the compound needs to be improved due to its chemical stability and selectivity, the clinical prospect is still exciting.

Method used

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  • Specific indole compound and its preparation and use in treating and preventing cancers
  • Specific indole compound and its preparation and use in treating and preventing cancers
  • Specific indole compound and its preparation and use in treating and preventing cancers

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0081] Experimental Example 1: Chemical Synthesis and Structure Confirmation of JN-2518

[0082] (1) Materials and methods

[0083] 1. Reagents: 2-keto indole (Oxindole), indoline diketone (Isatin), iodoethane, phosphorus pentachloride, hydroxylamine hydrochloride, acetic anhydride and toluene and other reagents were purchased from Sigma-Aldrich Chemical Reagent Company in the United States .

[0084] 2. Method: 2-ketoindole (3, Oxindole) was refluxed in acetic anhydride to obtain nitrogen acetylated product 5. Indoline dione (4, Isatin) and phosphorus pentachloride reaction in benzene solution obtained chlorinated intermediate 6 and compound 5 in anhydrous toluene immediately backflow 2 hours, after obtaining solid filtration, use toluene and ethanol successively Wash statically, recrystallize in dimethylamide to obtain compound 7, and then react with ethyl iodide under alkaline conditions to obtain nitrogen alkylation reaction product 8, and nitrogen ethylated product 8 is...

experiment example 2

[0087] Experimental example 2: Inhibitory effect of JN-2518 on human cancer cells

[0088] The following are some examples of JN-2518 and other priority compounds in the treatment of tumors. Here again, we reiterate that although we only use the treatment of tumors as an example, it does not mean that these compounds are only used to treat tumors.

[0089] (1) Materials and methods

[0090] Reagent: JN-2518 and its series of compounds, synthesized by our laboratory, confirmed the structure by mass spectrometry, NMR, infrared, and purified by high pressure liquid chromatography (HPLC). The purity was >98.0%. JN-2518 is a dark red crystalline powder with a molecular weight of 305. During the experiment, a solution was prepared with DMSO and stored at -20°C. Retinoic acid, daunorubicin, and paclitaxel were purchased from Sigma Chemical Reagent Company in the United States. NS389, a novel cyclooxygenase II inhibitor, was purchased from Biomol. Research Lab, USA. Unless other...

experiment example 3

[0107] Experimental example 3: The effect of JN-2518 on prostate cancer ascites metastasis cancer cells:

[0108] (1) Materials and methods

[0109] Reagent: JN-2518 see Experimental Example 1. Daunorubicin, paclitaxel, arsenic trioxide (As 2 o 3 ), Triochstatin A (TSA) was purchased from Sigma Chemical Reagent Company, USA. Unless otherwise specified, other chemical reagents used in the experiment were purchased from Sigma Chemical Reagent Company in the United States.

[0110] Cell culture: the primary cultured human cancer cell B1011 transferred from the ascites of prostate cancer was collected from the patient's ascites by centrifugation, and stored at 37°C, 5% CO 2 In an incubator, culture in RPMI1640 medium containing 10% fetal bovine serum and penicillin-streptomycin. After one week in culture, the cells grew rapidly and steadily. B1011 cancer cells in logarithmic growth phase were taken to study the anticancer activity of JN-2518 by MTT method.

[0111] MTT: The...

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Abstract

The invention relates to a series of organic heterocyclic compounds, JN-2518 series compounds and their preparation methods and their application in treating and preventing cancer and other diseases. The series of compounds are prepared through organic synthesis reactions and are used in the field of medicine. This series of compounds can specifically inhibit the activity of cell cycle kinases, block cell proliferation, and induce cell apoptosis, thereby effectively inhibiting the growth of various human tumor cells including colon cancer, prostate cancer, breast cancer, and neuroblastoma. The series of compounds have low toxicity and side effects, and can be used to treat various diseases of humans and animals, including the treatment and prevention of malignant tumors, senile dementia, psoriasis, cardiovascular diseases, glomerulonephritis and AIDS.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a series of indole heterocyclic compounds JN-2518, a preparation method and a medical application thereof. This series of compounds can specifically inhibit the activity of cell cycle kinases, and can be used to treat and prevent various diseases such as human and animal malignant tumors. Background technique [0002] Due to the advances in epidemiology, further improvements in early diagnosis and treatment methods, remarkable achievements have been made in the treatment and prevention of cancer in the past ten years. According to statistics from the American Cancer Society, since 1999, the incidence of cancer in the United States has shown a slight downward trend. Despite this, cancer remains one of the major life-threatening diseases in the United States. In my country, due to environmental pollution and people's bad living habits, the incidence of malignant tumors continues ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P9/10A61P13/12A61P17/06A61P25/28A61P31/18A61P35/00C07D209/40
CPCA61P9/10A61P13/12A61P17/06A61P25/28A61P31/18A61P35/00C07D209/40
Inventor 王龙贵程景才
Owner JC (WUXI) CO INC
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