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Dihydrofuran indenoane-imidazole salts compound and preparation method thereof

A technology of dihydrofuranoindenes and salt compounds, which is applied in the field of anti-cancer, and can solve problems such as bone marrow suppression, leukopenia, and nausea in patients

Inactive Publication Date: 2012-11-07
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the chemotherapeutic drugs in clinical use have side effects such as nausea, vomiting, leukopenia, and bone marrow suppression.

Method used

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  • Dihydrofuran indenoane-imidazole salts compound and preparation method thereof
  • Dihydrofuran indenoane-imidazole salts compound and preparation method thereof
  • Dihydrofuran indenoane-imidazole salts compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 1-(dihydrofuranoindan)-3-(naphthoylmethyl)imidazolium bromide

[0033]

[0034] The preparation process is as follows:

[0035] 1. Preparation of 5-formyl dihydrobenzofuran:

[0036] Under ice-water bath, slowly dropwise add phosphorus oxychloride (31.0ml, 0.333mol) into N,N-dimethylformamide (28.4ml, 0.366mol), react for 10 minutes, slowly dropwise add 2,3-di Hydrobenzofuran (1, 20.0g, 0.166mol), remove the ice-water bath, heat and stir at 85°C for 12 hours, pour the reaction system into ice water, add sodium hydroxide solution, adjust the pH value to 8-9, and use acetic acid Ethyl ether extraction, the organic phase washed with saturated brine, anhydrous Na 2 SO 4 After drying, filtering, and concentrating the solvent under reduced pressure, silica gel column chromatography (100-200 mesh) with petroleum ether-ethyl acetate (5:1) as the eluent was used to prepare 5-formyl dihydrobenzofuran ( 2, 22.8g), yield 93%;

[0037] 2. Preparation of 5-acrylic a...

Embodiment 2

[0053] Example 2 1-(Dihydrofuranoindan)-3-(phenacylmethyl)imidazolium bromide

[0054]

[0055] The preparation process is as follows:

[0056] The preparation of 1.5-formyl dihydrobenzofuran: method is the same as embodiment 1;

[0057] The preparation of 2.5-acrylic acid dihydrobenzofuran: method is the same as embodiment 1;

[0058] 3. The preparation of 5-propionic acid dihydrobenzofuran: the method is the same as in Example 1;

[0059] 4. The preparation of dihydrofuranoindanone: the method is the same as in Example 1;

[0060] 5. The preparation of dihydrofuroindanol: the method is the same as in Example 1;

[0061] 6. The preparation of 1-(dihydrofuranoindan) imidazole: the method is the same as in Example 1;

[0062] 7. Preparation of 1-(dihydrofuranoindan)-3-(phenacyl)imidazolium bromide:

[0063] Dissolve 1-(dihydrofuranoindan) imidazole (8a, 226mg, 1mmol) in acetone or toluene or 1,4-dioxane solvent (20ml), add phenacyl bromide (239mg, 1.2mmol), the reactio...

Embodiment 3

[0067] Example 3 1-(Dihydrofuranoindan)-3-(4-methoxyphenacylmethyl) imidazolium bromide

[0068]

[0069] The preparation process is as follows:

[0070] The preparation of 1.5-formyl dihydrobenzofuran: method is the same as embodiment 1;

[0071] The preparation of 2.5-acrylic acid dihydrobenzofuran: method is the same as embodiment 1;

[0072] 3. The preparation of 5-propionic acid dihydrobenzofuran: the method is the same as in Example 1;

[0073] 4. The preparation of dihydrofuranoindanone: the method is the same as in Example 1;

[0074] 5. The preparation of dihydrofuroindanol: the method is the same as in Example 1;

[0075] 6. The preparation of 1-(dihydrofuranoindan) imidazole: the method is the same as in Example 1;

[0076] 7. Preparation of 1-(dihydrofuranoindan)-3-(4-methoxyphenacyl)imidazolium bromide:

[0077] Dissolve 1-(dihydrofuranoindan)imidazole (8a, 226mg, 1mmol) in acetone or toluene or 1,4-dioxane solvent (20ml), add 4-methoxybenzoylform under st...

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Abstract

The invention discloses a series of dihydrofuran indenoane-imidazole salts compounds and a preparation method thereof. The preparation method comprises the following steps of: carrying out Vilsmeier reaction and Perskin reaction on 2,3-dihydrobenzofuran taken as a raw material; reducing palladium / carbon in an acetic acid to 5-propionic acid dihydrobenzofuran and forming acyl chloride with thionyl chloride; carrying out intramolecular Friedel-Crafts reaction and reducing in an alcohol solution by using sodium borohydride to obtain dihydrofuran indenoanol; forming a chloride in a toluene solution with the thionyl chloride; and reflowing and reacting with imidazole or 2-methyl imidazole or 2-ethyl imidazole or benzimidazole in acetonitrile or a toluene solvent to synthesize 1-(dihydrofuran indenoane) imidazole, and reacting with a halide on the above basis to synthesize the compound. According to the dihydrofuran indenoane-imidazole salts compounds and the preparation method thereof, pharmacophores with obvious tumor resisting activity in natural products are used as precursors to carry out designing and synthesizing on anti-tumor medicine molecule, and when an imidazole structure unit in a synthesized compound is the benzimidazole, particularly a naphthoyl methyl imidazole salts compound, the compound has very good in-vitro anticancer physiological activity.

Description

technical field [0001] The present invention relates to a novel dihydrofuranoindan-imidazolium salt compound and its preparation method, and the application of the pharmaceutical composition in which the compound is an active ingredient in anticancer. Background technique [0002] Cancer is a class of diseases that seriously threaten human health. The mainstay currently used to treat cancer is chemotherapy. Most of the chemotherapeutic drugs in clinical use have side effects such as nausea, vomiting, leukopenia, and bone marrow suppression. Therefore, finding highly active, non-toxic or low-toxic anticancer compounds has become an important topic in new drug research. Natural products and their related research are the source of pharmaceutical innovation. Search for physiologically active compounds from natural products, design and synthesize natural product-like libraries based on their molecular structure information, screen and discover lead compounds with high efficie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04A61K31/4184A61K31/4178A61P35/00
Inventor 羊晓东张洪彬陈文汪学全杨丽娟李良
Owner YUNNAN UNIV