Compound and synthesis method and application thereof

A technology of compound and glucose, which is applied in the field of preparation of drugs, can solve problems such as poor effect and side effects

Active Publication Date: 2019-08-09
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many marketed drugs for the treatment of this disease, in clinical use, many drugs, especially external drugs, have the disadvantages of poor efficacy or obvious side effects

Method used

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  • Compound and synthesis method and application thereof
  • Compound and synthesis method and application thereof
  • Compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0184] Embodiment 1: polycarcin V and its synthesis

[0185] Follow the steps below to synthesize polycarcin V:

[0186]

[0187] (1) Synthesis of compound 2:

[0188] Compound 1 (2.34 g, 9.24 mmol) was dissolved in 72 mL of anhydrous N,N-dimethylformamide at room temperature. Then the solution was cooled to 0° C. by ice-water bath, and sodium hydride (60% in mineral oil, 665 mg, 16.63 mmol) was added slowly and carefully. The resulting mixture was stirred for 30 minutes, then isopropyl iodide (1.88 mL, 18.48 mmol) was added via syringe. The reaction solution was heated to 70 °C and stirred overnight, then cooled to room temperature. The reaction solution was quenched by pouring into ice-cold water, and extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product. Separation and purification by silica gel column chromatography (petroleum ether / ethyl acetat...

Embodiment 2

[0220] Embodiment 2: Compound I-4 and its synthesis

[0221] Derivative 1-4 was synthesized according to the following steps:

[0222]

[0223] (1) Synthesis of Compound 23:

[0224] To a solution of aromatic ring 8 (43.7 mg, 0.125 mmol) and sugar donor 22 (49.8 mg, 0.105 mmol) in anhydrous dichloroethane (0.6 mL) was added at room temperature Molecular sieves (1.00g), tin tetrachloride (1.0M dichloroethane solution, 0.31mL, 0.305mmol). The reaction mixture was stirred at room temperature for 18 hours, then dichloromethane and saturated sodium bicarbonate solution were added. After separation of the organic phase, it was washed with water and then concentrated under reduced pressure. The residue was separated and purified by preparative thin layer chromatography (CH 2 Cl 2 / EtOAc=98 / 2) gave compound 8 (29.7 mg, 37%) as a yellow solid. Its characterization information is specifically:

[0225] 1 H NMR (400MHz, CDCl3) δ9.71(s, 1H), 8.22(s, 1H), 8.11–8.01(m, 2H), 7.75...

Embodiment 3

[0229] Embodiment 3: Compound 1-5 and its synthesis

[0230] Derivative 1-5 was synthesized according to the following steps:

[0231]

[0232] (1) Synthesis of Compound 25:

[0233]To a solution of aromatic ring 8 (400 mg, 1.204 mmol) and sugar donor 24 (105.0 mg, 0.301 mmol) in anhydrous dichloroethane (17.7 mL) was added tin tetrachloride (1.0 M dichloroethane solution, 2.7mL, 2.709mmol). The reaction mixture was stirred at room temperature for 46 hours, then dichloromethane and saturated sodium bicarbonate solution were added. After separation of the organic phase, it was washed with water and then concentrated under reduced pressure. The residue was separated and purified by preparative thin layer chromatography (CH 2 Cl 2 / EtOAc=98 / 2) gave compound 25 (15.1 mg, 8%) as a yellow solid. Its characterization information is specifically:

[0234] 1 H NMR (400MHz, CDCl3) δ9.52(s, 1H), 8.01–7.95(m, 3H), 7.68(d, J=8.8Hz, 1H), 7.15(s, 1H), 6.68(dd, J= 17.5,10.9Hz,1H),...

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Abstract

The invention relates to a compound and a synthesis method and application thereof. The compound has the structure shown in the general formula I. The compound has the quite good restraining activityfor different tumor cell lines and has the ideal anti-tumor and anti-skin-disease treatment effect under the illumination condition. The invention further relates to the synthesis method of the compound. A chemical full-synthesis route is adopted in the method; the converging type synthesis route can be applied to the chemical synthesis of similar-structure compounds and related derivatives, and the broad development space is developed for novel anti-tumor and anti-skin-disease medicines.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a light-controlled anti-tumor and anti-skin disease compound, and also relates to a chemical synthesis method of the compound and its application in the preparation of medicines. Background technique [0002] Malignant tumors are one of the leading causes of death in the world, and millions or even tens of millions of people die from such diseases every year [1] . The prevention, control and treatment of malignant tumors is an urgent medical problem to be solved. When genes that control processes such as cell proliferation and cell cycle are mutated, it will cause abnormal cell proliferation and eventually lead to the formation of malignant tumors [2] . Compared with normal cells, the energy metabolism of tumor cells is different, and their uptake of glucose is higher. In order to obtain higher nutrients, tumor tissue can continue to form new blood vessels during the format...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/04C07H19/056C07D311/78C07D405/06C07F9/6558A61P35/00A61P17/00A61P17/06
CPCA61P17/00A61P17/06A61P35/00C07D311/78C07D405/06C07D407/04C07F9/65586C07H19/056
Inventor 雷晓光吴凡岳宗伟郭富生
Owner PEKING UNIV
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