Unlock instant, AI-driven research and patent intelligence for your innovation.

Novel anticancer conjugates of camptothecin and unsaturated fatty acids

A technology of unsaturated fatty acid and camptothecin, which can be used in medical preparations with non-active ingredients, medical preparations containing active ingredients, organic chemistry, etc., and can solve the problems of sensitivity to toxic and side effects of chemotherapy drugs and accelerated cycle.

Inactive Publication Date: 2005-09-28
PANORAMA RES INC
View PDF0 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some normal cells such as bone marrow and intestinal mucosa also cycle faster, making them sensitive to the toxic side effects of chemotherapy drugs

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
  • Novel anticancer conjugates of camptothecin and unsaturated fatty acids
  • Novel anticancer conjugates of camptothecin and unsaturated fatty acids
  • Novel anticancer conjugates of camptothecin and unsaturated fatty acids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] The synthesis of embodiment 1. compound 3

[0118] tert-butyl 4-(4-nitrobenzyl)-1-piperazinecarboxylate (3). To tert-butyl 1-piperazinecarboxylate, 1 (0.74g, 4mmol), and 4-nitrobenzyl bromide, 2 (0.86g, 4mmol) in N,N-dimethylformamide (DMF, 5mL ) was added potassium carbonate (3 g), and the reaction mixture was stirred at room temperature for 4 hours. The product was extracted with ethyl acetate (50 mL), and the organic phase was washed with water (20 mL×3). The solution was dried over sodium sulfate and the solvent was removed in vacuo. Eluting with ethyl acetate, the product was purified by column chromatography to obtain solid 3 (1.22 g, 95% yield), mp 99-100°C.

[0119] 1 H NMR (DMSO-d6): 8.21-8.19 (d, 2H, J=8.8Hz, Ar-H), 7.61-7.59 (d, 2H, J=8.0Hz, Ar-H), 3.63 (s, 2H, CH 2 ), 3.34-3.30(m, 4H, partially blurred, 2×CH 2 ), 2.35-2.32 (m, 4H, 2×CH 2 ), 1.39(s, 9H, 3×CH 3 ).Analysis(C 16 h 23 N 3 o 4 ) C, H, N.

Embodiment 2

[0120] Embodiment 2. Synthesis of compound 5

[0121] tert-butyl 4-[4-(cis 4,7,10,13,16,19-docosahexenoyl)amino]benzyl-1-piperazinecarboxylate (5). To compound 3 (0.68g, 2.1mmol) in ethyl acetate (100mL) was added 10% Pd / C (0.1g), then at 60lb / inch 2The reaction mixture was hydrogenated under pressure for 2 hours. The product was filtered and the solvent was removed in vacuo to afford amine 4 (0.6 g, 97% yield), without further purification, to amine 4 (0.6 g, 2.06 mmol) dissolved in acetonitrile (90 mL) was added cis-4,7 , 10,13,16,19-docosahexaenoic acid (DHA, 0.67g, 2.0mmol), 2-(1-benzotriazol-1-yl)-1,1,3,3-tetra methyluronium hexafluorophosphate (HBTU, 0.94 g, 2.5 mmol), and N,N-diisopropylethylamine (2.1 mL). The reaction mixture was stirred overnight. The solvent was removed in vacuo and the product was purified by column chromatography eluting with ethyl acetate to afford oil 5 (0.91 g, 73% yield).

[0122] 1 H NMR (DMSO-d6): 9.84 (s, 1H, NH), 7.53-7.51 (d, 2H, J=...

Embodiment 3

[0123] Embodiment 3. Synthesis of compound 6

[0124] 1-[4-(cis-4,7,10,13,16,19-docohexenoyl)amino]benzylpiperazine (6). Compound 5 (0.85 g, 1.4 mmol) was dissolved in ethyl acetate (10 mL), then saturated anhydrous HCl dissolved in ethyl acetate (7 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes. The precipitate was filtered and washed with ethyl acetate to afford 6 (0.68 g, 90% yield). The product was used in the next reaction without purification.

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

No PUM Login to View More

Abstract

The present invention provides novel conjugates of camptothecin compounds and long-chain unsaturated fatty acid. The novel conjugates can be used to treat mammalian cell proliferative diseases such as cancer.

Description

field of invention [0001] The present invention relates to novel fatty acid derivatives of camptothecin compounds, their preparation and use as anticancer agents. Background of the invention [0002] Cancer cells do not contain molecular targets that are completely unrelated to the host. Consequently, most anticancer chemotherapy has been based primarily on an enhanced proliferation rate of cancer cells. Anticancer drugs kill rapidly dividing tumor cells in the S or G2-M phase of the cell cycle leaving silent tumor cells and normal cells in the G1 or G0 phase (Tannock, I.F. in DeVita et al., eds. : Principles and Practice of Oncology: 3-13, J.B. Lippincott, Philadelphia, 1989). The fraction of tumor cells that are dividing at any time varies according to the type of tumor and the stage of tumor growth. In general, accelerated circulating tumors such as lymphomas, testicular tumors, and some childhood tumors are more sensitive to chemotherapy than co...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22
CPCC07D491/22A61K47/542
Inventor Y·王
Owner PANORAMA RES INC
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com