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13-hydroxyl cytisine cinnamate ester compound having antitumor activity and preparation method thereof

A compound and hydroxyl technology, applied in the field of 13-hydroxycytisine cinnamate compounds and their preparation, can solve problems such as multi-drug resistance and treatment failure, and achieve enhanced drug efficacy, full utilization, and low production costs Effect

Active Publication Date: 2018-11-20
XIAN TAKOMED PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Tumor is a disease that seriously threatens human health. The mechanism of action of anti-tumor drugs on the market and the targets of drugs are diverse, and the multi-drug resistance of tumor cells often leads to the failure of treatment.

Method used

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  • 13-hydroxyl cytisine cinnamate ester compound having antitumor activity and preparation method thereof
  • 13-hydroxyl cytisine cinnamate ester compound having antitumor activity and preparation method thereof
  • 13-hydroxyl cytisine cinnamate ester compound having antitumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (Z)-(6S,7aR,13S,14aR)-tetradecahydro-6,13-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-2-yl 3-phenylacrylate ( Preparation of Compound A)

[0032] Put 25.02mg (0.10mmol) of 13-hydroxycytisine and 19.25mg (0.13mmol) of cinnamic acid in a reaction vessel, add 50mL of toluene to fully dissolve, add 2.46mg (0.02mmol) of 4-DMAP, 2.06mg ( 0.01mmol) DCC, reacted at 80°C for 8 hours, evaporated to dryness under reduced pressure, added ethyl acetate to dissolve the organic matter, washed the organic layer with water, sodium bicarbonate solution and brine, and dried, and recovered the solvent by rotary evaporation under reduced pressure. The concentrated solution was cooled and crystallized, and 29.00 mg of the target compound A was obtained by suction filtration, with a yield of 76.26%.

[0033]

[0034] 1 H-NMR (400MHz, DMSO- d 6 )δ(ppm): 7.60(2H,d), 7.32-7.40(4H,m), 6.59 (1H,d), 3.92(1H,s), 2.72-3.17 (4H,m), 2.64-2.72(4H ,m), 1.76-1.93 (4H,m), 1.48-1.69 (4H,m), 1.45-1.4...

Embodiment 2

[0036] (Z)-(6S,7aR,13S,14aR)-tetradecahydro-6,13-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-2-yl 3-(4 Preparation of -hydroxyphenyl)acrylate (compound B)

[0037] Put 25.02mg (0.10mmol) of 13-hydroxycytisine and 16.40mg (0.10mmol) of 4-hydroxycinnamic acid in a reaction vessel, add 50mL of acetonitrile to fully dissolve, then add 2.46 mg (0.02mmol) of 4-DMAP, 2.06mg (0.01mmol) DCC, reacted at 80°C for 12 hours, evaporated to dryness under reduced pressure, added ethyl acetate to dissolve the organic matter, washed the organic layer with water, sodium bicarbonate solution and brine, and dried, and rotated under reduced pressure The solvent was recovered by evaporation, the concentrated solution was cooled and crystallized, and 27.94 mg of compound B of the present invention was obtained by suction filtration, with a yield of 70.52%.

[0038]

[0039] 1 H-NMR (400MHz, DMSO- d 6 )δ(ppm):7.48(2H,d), 7.37(1H,d), 6.56 (2H,d), 5.90(1H,d), 5.28(1H,s), 5.19(1H,m), 2.58( 1H,m),...

Embodiment 3

[0041] (Z)-(6S,7aR,13S,14aR)-tetradecahydro-6,13-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-2-yl 3-(3 Preparation of -hydroxyphenyl)acrylate (compound C)

[0042]Put 25.02mg (0.10mmol) of 13-hydroxycytisine and 16.40mg (0.10mmol) of 3-hydroxycinnamic acid in a reaction vessel, add 50mL of toluene to fully dissolve, then add 2.46 mg (0.02mmol) of 4-DMAP, 1.92 mg (0.01 mmol) of EDC, reacted at 80°C for 4 hours, evaporated to dryness under reduced pressure, added ethyl acetate to dissolve the organic matter, washed the organic layer with water, sodium bicarbonate solution and brine, dried, and rotated under reduced pressure The solvent was recovered by evaporation, the concentrated solution was cooled and crystallized, and 27.13 mg of compound C of the present invention was obtained by suction filtration, with a yield of 68.48%.

[0043]

[0044] 1 H-NMR (400MHz, DMSO- d 6 )δ(ppm): 7.48(1H,t), 7.40(1H,d), 7.09 (1H,d),6.75 (1H,d), 6.62 (1H,s), 5.87(1H,d), 5.16( 1H,s), 5.1...

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Abstract

The invention discloses a 13-hydroxyl cytisine cinnamate ester compound having an antitumor activity and a preparation method of the 13-hydroxyl cytisine cinnamate ester compound. The 13-hydroxyl cytisine, the cinnamate and a derivative of the cinnamate are taken as the raw materials, and have an esterification reaction through an organic solvent and a condensing agent to synthesize the novel-structure 13-hydroxyl cytisine cinnamate ester compound. The compound can be used to prevent or treat tumor related diseases, and has a relatively important medical research value. The raw materials of the method are cheap and easy to get, the reaction condition is easy to control, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a class of 13-hydroxycytisine cinnamate compounds with antitumor activity and a preparation method thereof, belonging to the technical field of drug synthesis. Background technique [0002] Tumor is a disease that seriously threatens human health. The mechanism of action of anti-tumor drugs on the market and the targets of drugs are diverse. However, multi-drug resistance of tumor cells often leads to treatment failure. Finding anti-tumor drugs that are safe, effective, and less toxic and side effects has always been the goal pursued by researchers in the research and development of cancer drugs. [0003] The structure of cytisine (spartin) is shown in formula (II). Cytisine has a wide range of biological activities, such as anti-arrhythmia, anti-microbial infection, anti-ulcer, increasing white blood cells and so on. Cytisine has a wide range of sources, and can be extracted from plants such as leguminous plants Sophora flav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22A61P35/00
CPCA61P35/00C07D471/22
Inventor 梁承远田蕾同乾丹孟宣瑾史楷岐鞠星可刘玉枝温丽丽李菡王学川
Owner XIAN TAKOMED PHARMA TECH
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