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Cephalotamannine derivative, its production, its medicinal composition and use

A technology of mannine and derivatives, which can be applied in the preparation of anti-multidrug-resistant tumor drugs, and the application field in the preparation of anti-tumor drugs, and can solve the problems of large toxic and side effects, drug resistance, decreased efficacy and the like. question

Inactive Publication Date: 2013-01-16
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although paclitaxel and docetaxel have good therapeutic effects as anticancer drugs, due to the large toxic side effects and long-term use, drug resistance should be produced. At present, many tumor cell lines have developed drug resistance to paclitaxel and docetaxel. greatly reduce their efficacy

Method used

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  • Cephalotamannine derivative, its production, its medicinal composition and use
  • Cephalotamannine derivative, its production, its medicinal composition and use
  • Cephalotamannine derivative, its production, its medicinal composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1 Preparation of 10-deacetyl-cephalomanine

[0058]

[0059] Step 1: 2'-tert-butyldimethylsilyl-cephalomannine

[0060] Dissolve cephalomannine (600mg, 0.721mmol) in 5ml of DMF, add imidazole (245.5mg, 3.61mmol) and tert-butyldimethylchlorosilane (543.5mg, 3.61mmol), react at 70°C for 5 hours, add saturated NaHCO 3 10ml of the solution was extracted with ethyl acetate 3×50ml, the ethyl acetate layers were combined, dried over anhydrous sodium sulfate, the ethyl acetate layer was evaporated to dryness, silica gel column chromatography, petroleum ether: ethyl acetate = 5:1. Obtained 637 mg (93.4%) of the target product.

[0061] Step 2: 2'-tert-Butyldimethylsilyl-10-deacetyl-cephalomannine

[0062] Dissolve 2'-tert-butyldimethylsilyl-cephalomannine (98 mg, 0.103 mmol) in 6 ml of ethanol, add 85% hydrazine hydrate (0.625 ml), react at room temperature for 2 hours, add saturated NH4Cl solution 10ml, extracted with ethyl acetate 3×50ml, combined the ethyl acet...

Embodiment 2-4

[0066] Embodiment 2-4 is made by reacting following reaction scheme

[0067]

Embodiment 2

[0068] Example 2 Preparation of 2-(3-azidobenzoyl)-10-propionyl-cephalomannine

[0069]

[0070] Step 1-2: the same as the method described in step 1-2 in Example 1.

[0071] Step 3: 2'-tert-Butyldimethylsilyl-10-propionyl-cephalomannine

[0072] Dissolve 2'-tert-butyldimethylsilyl-10-deacetyl-cephalomannine (155mg, 0.171mmol) in 5mlTHF, add CeCl 3 (8.4mg), ice bath, add propionic anhydride (0.22ml, 1.71mmol), react at 30°C for 2 hours, add 300ml ethyl acetate, wash with saturated NaHCO 3 The solution was washed with 2×50ml, washed with 50ml saturated NaCl solution, the aqueous layer was extracted with 150ml ethyl acetate, the ethyl acetate layers were combined, dried over anhydrous sodium sulfate, filtered, the ethyl acetate layer was evaporated to dryness, silica gel column chromatography, acetone: Petroleum ether=1:2. 148.2mg (97%) of the target product was obtained.

[0073] Step 4: 2'-tert-Butyldimethylsilyl-7-triethylsilyl-10-propionyl-cephalomannine

[0074] 2'-...

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Abstract

A cephalotmannine derivative, composition containing it, its production and use are disclosed. It can be used to prepare drug-resisting medicine in treatment of tumor.

Description

technical field [0001] The invention discloses cephalomannine derivatives represented by the general formula (I), a preparation method of such cephalomannine derivatives, a composition containing such compounds, and the use of such compounds in the preparation of antitumor The application in medicine, especially the application in the preparation of anti-multidrug-resistant tumor drugs. Background technique [0002] Taxanes in terpenes are subjects of great interest in the fields of biology and chemistry. Among them, paclitaxel has good tumor inhibitory activity, and it has been used as an anticancer drug [0003] [0004] Wherein, Ac is acetyl, and Bz is benzoyl. [0005] Colin et al reported the paclitaxel analog docetaxel in U.S. Patent 4,814,470. Its activity is significantly higher than that of paclitaxel, and it is also listed as an anticancer drug. Its structural formula is as follows: [0006] [0007] Although paclitaxel and docetaxel have good therapeutic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D305/14A61K31/337A61P35/00
Inventor 方唯硕陈晓光杨春刚李轩王洪波刘红岩韩锐赵立敏
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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