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Monocarbonyl curcumin analogs, and preparation method and application thereof

The technology of monocarbonyl curcumin and carbonyl curcumin, which is applied in the field of medicine, can solve the problems of lack of research on the apoptosis induction mechanism of NCI-H460 cells, and achieve the effects of mild reaction conditions, simple preparation process and simple product molecular structure.

Inactive Publication Date: 2016-06-22
LIAOCHENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is a lack of research on monocarbonyl curcumin analogs and their preparation methods and the mechanism of apoptosis induction in NCI-H460 cells at home and abroad.

Method used

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  • Monocarbonyl curcumin analogs, and preparation method and application thereof
  • Monocarbonyl curcumin analogs, and preparation method and application thereof
  • Monocarbonyl curcumin analogs, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of 2,2'-fluoro monocarbonyl curcumin analog (A)

[0049]

[0050] 2-Fluorobenzaldehyde (2.48g, 20mmol) was dissolved in 8mL of absolute ethanol, acetone (0.74mL, 10mmol) was added, and 6mL of 20% sodium hydroxide was slowly added dropwise at -10°C, 0°C, and 10°C respectively After solution, stir at room temperature for 48 hours, add dilute hydrochloric acid to adjust the reaction system to pH = 5, filter, wash with water, and separate by n-hexane / ethyl acetate (15:1) column chromatography to obtain 2,2'-F-monocarbonyl curcumin , and the yields were 70%, 75%, and 68%, respectively. 1 HNMR (400MHz, CD 3 Cl), δ7.85(d, J=16.4Hz, 2H), 7.62(dt, J=7.6, 1.6Hz, 2H), 7.37-7.42(m, 2H), 7.12-7.23(m, 6H); 13 CNMR (100MHz, CD 3 Cl), δ189.0, 162.9, 160.4, 136.1, 131.9, 129.4, 127.6, 124.5, 122.9, 116.4.

Embodiment 2

[0052] Preparation of 3,3'-fluoro monocarbonyl curcumin analog (B)

[0053]

[0054] 3-Fluorobenzaldehyde (2.48g, 20mmol) was dissolved in 8mL of absolute ethanol, acetone (0.74mL, 10mmol) was added, and 6mL of 20% sodium hydroxide was slowly added dropwise at -10°C, 0°C, and 10°C respectively After solution, stir at room temperature for 48 hours, add dilute hydrochloric acid to adjust the reaction system to pH = 5, filter, wash with water, and separate by n-hexane / ethyl acetate (15:1) column chromatography to obtain 2,2'-F-monocarbonyl curcumin , and the yields were 50%, 62%, and 53%, respectively. 1 HNMR400MHz (CD 3 Cl), δ7.68(d, J=16.0Hz, 2H), 7.60-7.63(m, 4H), 7.10(t, J=7.6Hz, 4H), 6.98(d, J=16.0Hz, 2H); 13 HNMR100MHz (CD 3 Cl), δ188.4, 165.3, 162.8, 142.1, 131.0, 130.3, 125.1, 116.3, 116.0.

Embodiment 3

[0056] Preparation of 4,4'-fluoromonocarbonyl curcumin analog (C)

[0057]

[0058] 4-Fluorobenzaldehyde (2.48g, 20mmol) was dissolved in 8mL of absolute ethanol, acetone (0.74mL, 10mmol) was added, and 6mL of 20% sodium hydroxide was slowly added dropwise at -10°C, 0°C, and 10°C respectively After solution, stir at room temperature for 48 hours, add dilute hydrochloric acid to adjust the reaction system to pH = 5, filter, wash with water, and separate by n-hexane / ethyl acetate (15:1) column chromatography to obtain 2,2'-F-monocarbonyl curcumin , and the yields were 60%, 71%, and 59%, respectively. 1 HNMR400MHz (CD 3 Cl), δ7.69(d, J=16.0Hz, 2H), 7.55(d, J=8.7Hz, 4H), 6.89(d, J=8.7Hz, 4H), 6.64(d, J=15.9Hz, 2H), 5.98(s, 1H); 13 HNMR100MHz (CD 3 Cl), δ184.6, 160.6, 141.1, 131.0, 127.7, 122.1, 116.9, 101.8.

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Abstract

The invention discloses a monocarbonyl curcumin analogue, a preparation method and application thereof. The analogue has the structural features of general formula (I), wherein R is fluorine, the substitution positions of R are 2, 3, and 4-positions, and the two benzene rings pass through 1,4-pentadien-3-one connect. The invention uses o-, m-, p-fluorine substituted benzaldehyde as raw materials to generate monocarbonyl curcumin analogs through condensation with acetone. The stability of 2,2'-fluoromonocarbonyl curcumin in medium containing 10% serum is better than that of natural product curcumin. The results of pharmacological experiments showed that the anti-proliferation activity of fluorine-substituted monocarbonyl curcumin on human lung cancer NCI-H460 cells was significantly superior to that of natural product curcumin, and 2,2'-fluoro monocarbonyl curcumin could lead to cell proliferation by promoting the production of reactive oxygen species. Redox imbalance, lipid peroxidation, breakdown of mitochondrial membrane potential, and apoptosis in the body can be used as curcuminoid leads for the treatment of lung cancer.

Description

technical field [0001] The invention belongs to the technical field of medicines, and specifically relates to a monocarbonyl curcumin analogue, a preparation method and application thereof. Background technique [0002] In the past 50 years, the morbidity and mortality of lung cancer in the world have shown an obvious upward trend, and lung cancer has become a common malignant lung tumor that seriously threatens human health. In 2007, there were 213,380 new cases of lung cancer in the United States, and 160,390 deaths related to lung cancer. It is estimated that by 2030, the number of people who die from lung cancer will rank first in the cause of cancer death. Therefore, the drug treatment of lung cancer is still a research hotspot. [0003] Curcumin is a plant pigment extracted from the rhizome of turmeric and is the main active ingredient of turmeric. It has the characteristics of stable color and low toxicity, so it is widely eaten in Asian countries such as India and...

Claims

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Application Information

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IPC IPC(8): C07C49/235C07C45/74A61P35/00
CPCC07C49/235C07C45/74
Inventor 刘国运杨杰翟强周娜杜秀梅
Owner LIAOCHENG UNIV
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