Cephalotamannine derivative, its production, its medicinal composition and use

A technology of cephalomannine and its compounds, applied in the field of cephalomannine derivatives, can solve the problems of high toxicity and side effects, drug resistance, and decline in curative effect

Inactive Publication Date: 2007-11-21
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI +1
View PDF1 Cites 10 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

[0058] Example 1 Preparation of 10-deacetyl-cephalomanine

[0059]

[0060] Step 1: 2'-tert-butyldimethylsilyl-cephalomannine

[0061] 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.

[0062] Step 2: 2'-tert-Butyldimethylsilyl-10-deacetyl-cephalomannine

[0063] 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 NH 4 10ml of Cl solution was extracted with ethyl acetate 3×50ml, the ethyl aceta...

Embodiment 2-4

[0067] Embodiment 2-4 is made by reacting following reaction scheme

[0068]

Embodiment 2

[0069] Example 2 Preparation of 2-(3-azidobenzoyl)-10-propionyl-cephalomannine

[0070]

[0071] Step 1-2: the same as the method described in step 1-2 in Example 1.

[0072] Step 3: 2'-tert-Butyldimethylsilyl-10-propionyl-cephalomannine

[0073] 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 Solution 2 × 50ml was washed, 50ml saturated NaCl solution was washed, 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.

[0074] Step 4: 2'-tert-Butyldimethylsilyl-7-triethylsilyl-10-propionyl-cephalomannine

[0075] 2'-tert-but...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Weightaaaaaaaaaa
Login to view more

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 listed as an anticancer drug with the following structure: [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 ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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 AN INST OF THE CHINESE ACAD OF MEDICAL SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap