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Phalin c and its derivatives and their application in the preparation of anticancer drugs

A derivative, kalinin technology, applied in the field of kalinin C derivatives and its preparation of anticancer drugs, can solve the problems of low biological activity and large dosage

Active Publication Date: 2011-12-14
GUANGZHOU LEADER BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantages of the biologically active stilbene derivatives that have been found so far are low biological activity and large clinical dosage.

Method used

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  • Phalin c and its derivatives and their application in the preparation of anticancer drugs
  • Phalin c and its derivatives and their application in the preparation of anticancer drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1. Preparation of 2-isoamyl-3,5-dimethoxy-stilbene (DT-1).

[0014] Weigh 0.5g (1.7mmol) of lignanin C, add K after grinding 2 CO 3 0.23g (1.7mmol), add 50ml of acetone, add Me dropwise under stirring 2 SO 4 0.2ml (1.7mmol), reacted at 30°C for 6h, filtered, concentrated, and purified by 200~300 mesh silica gel column chromatography (petroleum ether: ethyl acetate = 19:1 as eluent) to obtain a white solid (DT-1 ) 0.48g, the yield was 91.6%. m.p.60-61℃; 1 HNMR (CDCl 3 )δ (ppm): 1.67 (s, 3H), 1.80 (s, 3H), 3.43 (d, J=6.6Hz, 2H), 3.78 (s, 3H), 3.82 (s, 3H), 5.13 (t, J=6.6Hz,1H), 6.41(s,1H), 6.74(s,1H), 6.96(d,J=16.2Hz,1H), 7.24(t,J=7.8Hz,1H), 7.34(t, J=7.8Hz, 2H), 7.36(d, J=16.2Hz, 1H), 7.48(d, J=7.8Hz, 2H). ESI-MS m / z 309 ([M+1] + ,100%). Anal. Calcd for C 21 h 24 o 2 : C, 81.78; H,, 7.84. Found: C, 65.77; H, 7.86.

Embodiment 2

[0015] Example 2. Preparation of 2-isoamyl-3-methoxy-5-chloropropoxy-stilbene (DT-2).

[0016] Weigh 0.25g (0.85mmol) of lignanin C, add anhydrous K after grinding 2 CO 3 0.1g (0.85mmol), add DMF10ml, under the protection of nitrogen, add 0.084ml (5mmol) of 1,3-bromochloropropane dropwise, stir at 30°C for 6h, filter, add 25ml ethyl acetate to the filtrate, and then use 3×10ml water Extraction, anhydrous Na 2 SO 4 Dry overnight, filter, concentrate, and purify by 200-300 mesh silica gel column chromatography (petroleum ether: ethyl acetate = 19:1 as eluent) to obtain 0.28 g of white solid (DT-2), with a yield of 88.8% . m.p.62-63℃; 1 H NMR (CDCl 3 )δ(ppm): 1.67(s,3H), 1.80(s,3H), 2.25(m,2H), 3.43(d,J=7.2Hz,2H), 3.76(t,J=6.3Hz,2H) , 3.81(s,3H), 4.16(t,J=5.7Hz,2H), 5.12(t,J=7.2Hz,1H), 6.42(s,1H), 6.76(s,1H), 6.96(d, J=16.2Hz,1H), 7.25(t,J=7.8Hz,1H), 7.35(t,J=7.8Hz,2H), 7.36(d, J=16.2Hz,1H), 7.50(d,J= 7.8Hz, 2H). ESI-MS m / z371 ([M+1] + ,10%). Anal. Calcd for C 23 h ...

Embodiment 3

[0017] Example 3. Preparation of 2-isoamyl-3-methoxy-5-propargyloxy-stilbene (DT-3).

[0018] Weigh 0.25g (0.85mmol) of lignanin C, add anhydrous K after grinding 2 CO 3 0.1g (0.85mmol), add DMF10ml, under the protection of nitrogen, drop 0.084ml (5mmol) of 1,3-bromochloropropane, stir at 30°C for 6h, then raise the temperature to 65°C, react for 6h, filter, add acetic acid to the filtrate Ethyl ester 25ml, then extracted with 3×10mL water, anhydrous Na 2 SO 4 Dry overnight, filter, concentrate, and purify by 200-300 mesh silica gel column chromatography (petroleum ether: ethyl acetate = 18:2 as eluent) to obtain 0.23 g of white needle-like crystals (DT-3). The yield is 81.6%. m.p.130-131℃; 1 H NMR(DMSO)δ(ppm): 1.60(s,3H), 1.75(s,3H), 2.20(m,1H), 3.39(d,J=6.6Hz,2H), 3.76(s,3H), 4.22(t,J=6Hz,2H), 4.99(t,J=6.6Hz,1H), 6.53(s,1H), 6.87(s,1H), 7.13(d,J=16.2Hz,1H), 7.27 (t, J=7.2Hz, 1H), 7.36(d, J=16.2Hz, 1H), 7.37(t, J=7.8Hz, 2H), 7.50(d, J=7.2Hz, 2H). ESI-MS m / z 331 ([M-1]...

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Abstract

Phylogenin C and its derivatives and their application in the preparation of anticancer drugs, the general formula of phyloganin C and its derivatives is: wherein, R=H, CH3, (CH2)3Cl, CH2CCH, SO2Ph, CH2Ph , CH2COOCH3, etc., phyloganin C and its derivatives of the present invention have significant inhibitory effects on various tumor cell lines such as lung cancer, lung adenocarcinoma, liver cancer, breast cancer, uterine cancer, etc., and have significant inhibitory effects on normal cells. It can be prepared as a medicine for treating cancer in the form of injection, tablet capsule, suspension or emulsion.

Description

technical field [0001] The invention relates to a class of lignanin C derivatives and their application in the preparation of anticancer drugs. technical background [0002] Cancer is a disease that seriously endangers human health. Finding drugs with high efficiency and low side effects is the main direction of anticancer drug research and development. [0003] The diversity of structures and biological activities of natural products makes them occupy a very important position in the history of drug research. Taking active natural products as lead compounds and modifying their structures to obtain highly efficient and low-toxic drugs is one of the important ways to develop new drugs. Among them, stilbene compounds have inhibitory effects on various cancer cells such as lung cancer, liver cancer, leukemia, pituitary adenoma, kidney cancer, colon cancer, ovarian cancer, breast cancer, central nervous system tumors, cervical cancer, and nasopharyngeal cancer. However, the di...

Claims

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Application Information

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IPC IPC(8): C07C43/215C07C43/225C07C43/23C07C41/16C07C41/01C07C41/20C07C309/73C07C303/28C07C69/708C07C69/157C07C67/31C07C67/08C07D307/79C07D311/58A61K31/085A61K31/09A61K31/255A61K31/22A61K31/222A61K31/343A61K31/353A61P35/00
Inventor 陆豫邱声祥洪挺余勃
Owner GUANGZHOU LEADER BIO TECH
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