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Isophyllenone-caprolactam derivatives and their preparation methods and applications

A ketone compound and tetramethyl technology, applied in the field of isofyl ketone caprolactam derivatives and their preparation, can solve the problems of toxicity accumulation, low antitumor activity and the like, and achieve good inhibitory activity, abundant sources, and synthesis technology. simple effect

Active Publication Date: 2022-03-04
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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  • Isophyllenone-caprolactam derivatives and their preparation methods and applications
  • Isophyllenone-caprolactam derivatives and their preparation methods and applications
  • Isophyllenone-caprolactam derivatives and their preparation methods and applications

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, a preparation method and an application thereof. The present invention uses isolongifolyl caprolactam derivatives as raw materials and cinnamoyl chloride derivatives as acylating reagents to undergo an acylation reaction under the catalysis of a base to prepare 3-cinnamoyl-5,5,9,9 ‑Tetramethyl‑4, 5, 6, 7, 8, 9‑hexahydro‑5a, 8‑endomethylenebenzo[d]azepine‑2(3H)‑ketones. The application has been proved by experiments that 3-cinnamoyl-5,5,9,9-tetramethyl-4,5,6,7,8,9-hexahydro-5a, 8-endomethylene benzo[d The ]azepine-2(3H)-ketone compound has good inhibitory activity on human breast cancer cell MCF-7, and has potential application value in the preparation of anti-tumor 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 Patents(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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