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Application of saccharide coupled-1, 2, 3-triazole substituted polycyclic aromatic hydrocarbon derivative in preparation of anti-cancer drug

A polycyclic aromatic hydrocarbon, anticancer drug technology, applied in the field of biopharmaceutical chemical synthesis, can solve problems such as severe cardiotoxicity

Inactive Publication Date: 2018-02-02
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, clinical studies have found that doxorubicin, as an antineoplastic drug, has severe cardiotoxicity in the application process, which can cause delayed severe heart failure (Tex Heart Inst J.2012; 39(3):424-427)

Method used

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  • Application of saccharide coupled-1, 2, 3-triazole substituted polycyclic aromatic hydrocarbon derivative in preparation of anti-cancer drug
  • Application of saccharide coupled-1, 2, 3-triazole substituted polycyclic aromatic hydrocarbon derivative in preparation of anti-cancer drug
  • Application of saccharide coupled-1, 2, 3-triazole substituted polycyclic aromatic hydrocarbon derivative in preparation of anti-cancer drug

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Experimental program
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preparation example Construction

[0058] 1) Preparation of alkynyl-substituted polycyclic aromatic hydrocarbon raw materials

[0059]

[0060] 2) Preparation of target derivatives of the present invention

[0061]

[0062] In general formula 1), starting from commercially available raw material brominated polycyclic aromatic hydrocarbons, according to the aromatic alkynylation method and conditions reported in the literature (Angewandte Chemie-International Edition, 2005, vol.44, #39p.6362-6366 ; Chemistry-A European Journal, 1999, vol.5, #11p.3366-3381; Journal of Organic Chemistry, 1999, vol.64, #8p.2704-2710), can successfully prepare alkynyl-substituted polycyclic aromatic hydrocarbons.

[0063] The coupling reaction between brominated polycyclic aromatic hydrocarbons and trimethylethynyl silane is generally carried out in the presence of metal palladium catalysts and copper salts. The metal palladium catalysts that can be used include tetrakis (triphenylphosphine) palladium, bistriphenylphosphine P...

Embodiment 1

[0074]

[0075] The preparation method of compound I-1: comprises the following steps:

[0076]

[0077] (1) Synthesis of Compound II-1

[0078] Bromocorannene pale yellow solid (198.2 mg), bistriphenylphosphine palladium dichloride (19.6 mg), cuprous iodide (5.1 mg), trimethylethynyl silicon (153.0 mg) were dissolved in dry THF solution (10mL) and triethylamine (5mL) were stirred at 70°C for 3h. After the reaction was completed, 10% hydrochloric acid (3×10mL) was added to the reaction solution, then extracted with ethyl acetate (25mL), washed with distilled water (1×50mL), saturated brine (1×50mL), and then washed with After drying over anhydrous sodium sulfate, the solvent was evaporated to dryness with a rotary evaporator, and the obtained crude product was purified by silica gel column chromatography (mobile phase = 100% double-distilled petroleum ether) to obtain 139.1 mg of a yellow solid. The obtained solid (116.0 mg) and potassium carbonate (9.4 mg) were dissol...

Embodiment 2

[0084]

[0085] The preparation method of compound 1-2, comprises the following steps

[0086]

[0087] Compound II-1 (50.0 mg) and compound III-2 (75.0 mg) (compound III-2 can be purchased commercially, or prepared by a synthetic method reported in the literature. Reference Chemistry-A European Journal, 2013, vol.19 , #45p.15346-15357) was added to a mixture of tert-butanol and water (4mL) with a volume ratio of 1:1, and then copper sulfate pentahydrate (23.0mg) and sodium ascorbate (73.0mg) were added in one go. Stir at 90°C for 24h. After the reaction was completed, 25 mL of dichloromethane was added to the reaction solution, and then washed with distilled water (1×50 mL), the aqueous phase was extracted with dichloromethane (2×25 mL), the organic phases were combined, and then dried over anhydrous sodium sulfate. The solvent was evaporated to dryness with a rotary evaporator, and the obtained crude product was purified by silica gel column chromatography (petroleum ...

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Abstract

The invention discloses the application of a saccharide coupled-1, 2, 3-triazole substituted polycyclic aromatic hydrocarbon derivative in the preparation of an anti-cancer drug. The structure of thesaccharide coupled-1, 2, 3-triazole substituted polycyclic aromatic hydrocarbon derivative is shown as the formula (I). A pharmacology experiment proves that the saccharide coupled-1, 2, 3-triazole substituted polycyclic aromatic hydrocarbon derivative has different degrees of inhibiting effects on lung cancer (H460), gastric cancer (HGC27), myeloma (H929), cervical cancer (Hela), liver cancer (HepG2), prostatic cancer (DU145) and colon cancer (HT29).

Description

technical field [0001] The invention belongs to the technical field of biopharmaceutical chemical synthesis, and in particular relates to the use of sugar-coupling-1,2,3-triazole-substituted polycyclic aromatic hydrocarbon derivatives in the preparation of anticancer drugs. Background technique [0002] PAHs are generally classified as chemicals with chronic toxicity. As π-electron-dense polycyclic aromatic hydrocarbon derivatives, they can interact with DNA macromolecules, causing DNA damage, such as forming DNA adducts, inducing DNA strand breaks, and the like. DNA strand break is an important type of DNA damage. When the base pairs in the DNA chain of cancer cells are broken or melted due to the insertion of π-electron-dense polycyclic aromatic hydrocarbon compounds, cancer cells cannot continue to replicate DNA leads to apoptosis. For example, there are many studies and reports (J.Med.Chem.1997,40,3734-3738; J Immunol.2007Dec 1; 179(11):7415- 7423; Drug Discov Ther. 2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/056C07H1/00A61P35/00
CPCC07B2200/07C07H1/00C07H19/056
Inventor 高清志石蕴丽黄振华
Owner TIANJIN UNIV
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