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Isolongifolenone caprolactam derivative as well as preparation method and application thereof

A technology of phyllenone and caprolactam, which is applied in the fields of medicinal chemistry and pharmacotherapeutics, can solve the problems of accumulation of toxicity and low anti-tumor activity, and achieve the effect of abundant sources and favorable industrial production

Active Publication Date: 2020-11-06
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the antitumor activity of isolongifolenone and its derivatives is low, and high dose administration is required to obtain the desired drug effect, which in turn will cause toxicity accumulation and limit its further development

Method used

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  • Isolongifolenone caprolactam derivative as well as preparation method and application thereof
  • Isolongifolenone caprolactam derivative as well as preparation method and application thereof
  • Isolongifolenone caprolactam derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 3-(4′-fluoro)cinnamoyl-5,5,9,9-tetramethyl-4,5,6,7,8,9-hexahydro-5a,8-methanobenzo[d ] Preparation of azepine-2 (3H)-ketone (compound 1):

[0024]

[0025] Add 5,5,9,9-tetramethyl-4,5,6,7,8,9-hexahydro-5a,8-methanobenzo[d]azepine sequentially into a 50mL one-necked flask In-2(3H)-ketone (0.5mmol), triethylamine (5mmol) and anhydrous dichloromethane (20mL), add p-fluorocinnamoyl chloride (0.5mmol) dropwise under ice bath, and react at room temperature for 4h after the dropwise addition , TLC detected that the reaction was complete, added water, extracted with dichloromethane, combined, concentrated, and purified by column chromatography (petroleum ether:ethyl acetate=4:1) to obtain a white solid powder with a yield of 74.5%. 1 HNMR (600MHz, CDCl 3 )δ: 7.64(d, J=15.5Hz, 1H), 7.54(dd, J=8.6, 5.5Hz, 2H), 7.21(d, J=15.6Hz, 1H), 7.04(t, J=8.6Hz, 2H), 5.74(s, 1H), 4.11(d, J=14.4Hz, 1H), 3.56(d, J=14.4Hz, 1H), 1.97(s, 1H), 1.89-1.91(m, 1H), 1.78-1.83(m, 1H), 1.72(d, J=7....

Embodiment 2

[0027] 3-(4′-methyl)cinnamoyl-5,5,9,9-tetramethyl-4,5,6,7,8,9-hexahydro-5a,8-methanobenzo[ d] Preparation of azepine-2(3H)-one (compound 2):

[0028]

[0029] The preparation method is the same as in Example 1, replacing p-fluorocinnamoyl chloride with p-methylcinnamoyl chloride, and the product 3-(4′-methyl)cinnamoyl-5,5,9,9-tetramethyl-4,5,6, 7,8,9-hexahydro-5a,8-methanobenzo[d]azepin-2(3H)-one is a white solid powder with a yield of 73.8%. 1 H NMR (600MHz, CDCl 3 )δ: 7.68(d, J=15.5Hz, 1H), 7.45(d, J=8.1Hz, 2H), 7.25(d, J=15.5Hz, 1H), 7.16(d, J=7.9Hz, 2H) , 5.74(s, 1H), 4.10(d, J=14.5Hz, 1H), 3.56(d, J=14.5Hz, 1H), 2.35(s, 3H), 1.96(s, 1H), 1.88-1.93( m, 1H), 1.77-1.82(m, 1H), 1.71(d, J=10.2, 1H), 1.51-1.57(m, 1H), 1.39(d, J=10.1Hz, 1H), 1.27-1.32( m, 1H), 1.16(s, 3H), 1.09(s, 3H), 1.05(s, 3H), 0.96(s, 3H); 13 C NMR (151MHz, CDCl 3 )δ:176.42,170.11,170.02,142.90,140.15,132.53,129.44,128.25,120.99,114.25,63.70,49.14,46.07,45.47,37.68,34.34,28.90,28.76,25.37,24.82,24....

Embodiment 3

[0031] 3-(4′-chloro)cinnamoyl-5,5,9,9-tetramethyl-4,5,6,7,8,9-hexahydro-5a,8-methanobenzo[d ] Preparation of azepine-2 (3H)-ketone (compound 3):

[0032]

[0033] The preparation method is the same as in Example 1, replacing p-fluorocinnamoyl chloride with p-chlorocinnamoyl chloride, and the product 3-(4'-chloro)cinnamoyl-5,5,9,9-tetramethyl-4,5,6,7, 8,9-hexahydro-5a,8-methanobenzo[d]azepin-2(3H)-one is a white solid powder with a yield of 77.8%. 1 H NMR (600MHz, CDCl 3 )δ: 7.64(d, J=15.6Hz, 1H), 7.51(d, J=8.5Hz, 2H), 7.34(d, J=8.5Hz, 2H), 7.27(d, J=15.7Hz, 1H) , 5.76(s, 1H), 4.14(d, J=14.5Hz, 1H), 3.58(d, J=14.4Hz, 1H), 1.98(m, 1H), 1.91-1.95(m, 1H), 1.80- 1.84(m, 1H), 1.74(d, J=10.1, 1H), 1.60-1.53(m, 1H), 1.43(d, J=10.2, 1H), 1.30-1.35(m, 1H), 1.19(s , 3H), 1.12(s, 3H), 1.08(s, 3H), 0.98(s, 3H); 13 C NMR (151MHz, CDCl 3 )δ: 176.86, 170.04, 169.71, 141.04, 135.58, 133.81, 129.37, 128.96, 122.68, 114.08, 63.75, 49.12, 46.06, 45.54, 37.67, 34.31, 28.87, 28.79, 24.2.2

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Abstract

The invention discloses an isolongifolenone caprolactam derivative as well as a preparation method and application thereof. The 3-cinnamoyl-5,5,9,9-tetramethyl-4,5,6,7,8,9-hexahydro-5a,8-bridged methylene benzo[d]azepine-2(3H)-one compound is prepared by taking an isolongifolenone caprolactam derivative as a raw material and taking a cinnamoyl chloride derivative as an acylation reagent through acylation reaction under the catalytic action of alkali. Experiments prove that the 3-cinnamoyl-5,5,9,9-tetramethyl-4,5,6,7,8,9-hexahydro-5a,8-bridged methylene benzo[d]azepine-2(3H)-one compound has good inhibitory activity on human breast cancer cells MCF-7, and has potential application value in preparation of antitumor drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and pharmacotherapeutics, and specifically relates to an isolongifolenone caprolactam derivative and a preparation method and application thereof. Background technique [0002] Isolongifolenone (Isolongifolenone) is an important derivative of longifolene, the main component of natural product turpentine. Its structure contains α, β-unsaturated ketone, and has many biological activities, such as anti-inflammatory, anti-virus, anti-fungal, anti-tumor etc. In recent years, studies have shown that isolongifolenone and its derivatives can increase the level of ROS in tumor cells, thereby killing tumor cells. However, the antitumor activity of isolongifolenone and its derivatives is low, and high dose administration is required to obtain the desired drug effect, which in turn will cause toxicity accumulation and limit its further development. [0003] Cyclic lactams and their derivatives have a vari...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/32A61P35/00
CPCC07D223/32A61P35/00
Inventor 王石发王芸芸张成龙赵雨珣徐徐杨益琴王忠龙
Owner NANJING FORESTRY UNIV
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