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Erythromycin derivative and application thereof

A technology of erythromycin derivatives and structural formula, applied in the field of medicine, can solve the problem that the activity of erythromycin derivative tumor cell proliferation has not been reported in literature and the like

Inactive Publication Date: 2009-12-09
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The relationship between erythromycin derivatives and tumor therapy has attracted people's attention, but the activity of erythromycin derivatives to directly inhibit tumor cell proliferation has not been reported in the literature

Method used

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  • Erythromycin derivative and application thereof
  • Erythromycin derivative and application thereof
  • Erythromycin derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0152] Embodiment 1: the preparation of compound 1

[0153] Step A

[0154] Dissolve erythromycin (6.00 g, 8.18 mmol) in 100 mL of methanol, then add NaBH 4 (0.93g, 24.54mmol), stirred at room temperature for 24h. Then 10 mL of distilled water was added and methanol was distilled off, then the solution was poured into water and extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. The solution was then concentrated and evaporated to dryness, and the resulting crude product was purified by silica gel column chromatography (chloroform:methanol:ammonia=10:0.5:0.01~10:1:0.05) to obtain 4.38g of 9(S)-hydroxyerythromycin in a yield of 70 %.

[0155] Step B

[0156] The product obtained in step A (3.00 g, 4.08 mmol), sodium acetate (2.80 g, 20.4 mmol) were dissolved in 100 mL of methanol and 20 mL of water. Then iodine (1.24 g, 4.90 mmol) was added, the reaction was stirred at 50°C for 6 h, and the pH of the solution was controlled to 8.0-9.0 with...

Embodiment 2

[0159] Embodiment 2: the preparation of compound 2

[0160] Using roxithromycin as a raw material, the title compound was prepared in the same manner as steps B and C in Example 1, with a yield of 88%; MS 837.4[M / 2+H] + ; compound 13 See Table-1 for C-NMR.

Embodiment 3

[0161] Embodiment 3: the preparation of compound 3

[0162] Step A

[0163] Erythromycin (12.00g, 16.36mmol), triethylamine (5.71mL, 40.90mmol) and hydroxylamine hydrochloride (5.70g, 81.98mmol) were dissolved in 12mL of methanol, stirred and refluxed for 24h. Then the reaction solution was cooled to 0° C., at which time a solid precipitated out, which was filtered and the filter cake was washed twice with cold methanol. Dissolve the solid in 10 mL of methanol, add 4 mL of ammonia water to the solution, stir for 30 minutes, and then add 4 mL of distilled water. Subsequently, crystals were precipitated, and 10 mL of distilled water was added, filtered with suction, and dried to obtain 6.36 g of 9(E)-erythromycin oxime as a white solid, with a yield of 52%.

[0164] Step B

[0165] The product obtained in Step A (0.85 g, 1.13 mmol) was dissolved in 10 mL of anhydrous ether and 1 mL of DMF, and NaH (95%) (42.69 mg, 1.69 mmol) was added to the solution. When no more gas was ge...

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Abstract

The invention belongs to the technical field of medicine, which relates to an erythromycin derivative. The structure of the erythromycin derivative is shown as formula (I): in the structural formula (I), a and e can be selected from 0 and 1, b, c and d can be selected from 0, 1, 2 and 3, but a, b, c, d and e can not be 0 simultaneously. The invention also provides innoxious salt and a hydrated substance thereof which are formed by the derivative shown in the structural formula and are acceptable in pharmacy. The derivative has better tumour-suppressing activity, and can be used for the application of a tumour cell propagation suppressor in the aspect of preparing anti-tumour medicines.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to an erythromycin derivative, a preparation method thereof, and an application as a tumor cell proliferation inhibitor in the preparation of antitumor drugs. Background technique [0002] Malignant tumor is a serious disease that threatens human health and life, and it is an important cause of death in China. [0003] Erythromycin (erythromycin) is the first macrolide antibiotic with clinical practical value discovered by human beings. It is mainly used to treat various infections caused by Gram-positive bacteria; ), telithromycin (telithromycin) and other erythromycin derivatives have good antibacterial activity, and are commonly used clinical anti-infective drugs. In addition to antibacterial activity, erythromycin derivatives also exhibit other biological activities, including promoting digestive tract motility, anti-inflammatory activity, antagonizing luteinizing hormone releas...

Claims

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Application Information

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IPC IPC(8): C07H17/08A61K31/7048A61P35/00
Inventor 张为革包凯吴英良梁隆祝华军程志鹏张传良田亮
Owner SHENYANG PHARMA UNIVERSITY
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