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Paeonol thiazole derivative and preparation method and application thereof

A technology of paeony phenothiazole derivatives, which is applied in the field of paeony phenothiazole derivatives and its preparation, can solve the problems that there are no public reports on paeony phenothiazole derivatives, and achieve improved anti-tumor activity, stable quality, The effect of high purity

Active Publication Date: 2019-07-05
GUILIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many reports in the existing literature that a series of paeonol derivatives have been obtained through structural modification on the paeonol core, there is no public report on paeonol and thiazole combination to obtain paeonol phenothiazole derivatives

Method used

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  • Paeonol thiazole derivative and preparation method and application thereof
  • Paeonol thiazole derivative and preparation method and application thereof
  • Paeonol thiazole derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of paeonol thiosemicarbazone 2

[0032] Add 33mmol of thiosemicarbazide and 40mL of absolute ethanol to a 250mL dry round-bottom flask, heat, stir and reflux at 80°C for 30min, slowly add 60mL of hot paeonol (30mmol) in absolute ethanol In the round bottom flask, add the concentrated sulfuric acid of 1mL again, continue to heat and stir reaction, TLC tracks reaction progress (V 氯仿 :V 甲醇 =10:1), stop the reaction after 20 h of reaction, add 80 mL of ice water, filter and wash to obtain 5.4 g of light yellow solid with a yield of 75.2%; m.p. 187.2-189.0°C; IR (KBr, cm -1 ) : 3562 (OH), 3379 (NH 2 ), 3271 (NH), 3138, 2976, 2841, 1624(C=N), 1589, 1514, 1479, 1340, 1253, 1166, 1080, 970, 837, 792, 744; MS (ESI)m / z 240.0 ([M+H] + );

[0033] Therefore, above-mentioned compound 2 is paeonol thiosemicarbazone, and its structural formula is as follows:

[0034] .

Embodiment 2

[0035] Example 2: N Preparation of -(4-phenylthiazol-2-yl)-2-hydroxy-4-methoxyacetophenone hydrazone 4a

[0036] Add 1 mmol paeonol thiosemicarbazone and 1 mmol compound 3a in a 100 mL round bottom flask, add 20-80 mL absolute ethanol, stir and reflux at 80 °C, and monitor the reaction progress by TLC (V 石油醚 :V 乙酸乙酯 =3:1). After the reaction, cool, filter, wash the precipitate with absolute ethanol, dry, and recrystallize with absolute ethanol and chloroform to obtain the solid product 4a, a light yellow solid, with a yield of 73.0%; m.p. 195.0-196.1 ℃; IR (KBr, cm -1 ): 3412 (OH), 3232 (NH), 3049, 2931,2849, 1620 (C=N), 1591, 1510, 1454, 1363, 1282, 1199, 1155, 1111, 1025, 975,858, 754, 671; 1 H NMR (600 MHz, DMSO) δ 7.86 (d, J = 7.5 Hz, 2H, H-2’, H-6’),7.50 (d, J = 8.5 Hz, 1H, H-4’), 7.42 (t, J = 7.2 Hz, 2H, H-3’, H-5’), 7.32(t, J = 7.1 Hz, 1H, H-6’), 7.28 (s, 1H, H-10), 6.49 (d, J = 15.1 Hz, 2H, H-5,H-3), 3.76 (s, 3H, OCH 3 ), 2.40 (s, 3H, CH 3 ); 13 C NMR...

Embodiment 3

[0039] Example 3:N Preparation of -[4-(2-hydroxyphenyl)thiazol-2-yl]-2-hydroxy-4-methoxyacetophenone hydrazone 4b

[0040] In a 100 mL round bottom flask, add 1 mmol paeonol thiosemicarbazone and 1 mmol compound 3b, add 20-80 mL absolute ethanol, stir and reflux reaction at 80 ° C, TLC monitors the reaction process (V 石油醚 :V 乙酸乙酯 =3:1). After the reaction, cool, filter, wash the precipitate with absolute ethanol, dry, and recrystallize with absolute ethanol and chloroform to obtain a yellow solid 4b with a yield of 82.3%; m.p.231.0-234.0 ℃; IR (KBr, cm -1 ) : 3414 (OH), 3097, 2937, 2841, 1620 (C=N),1516, 1458, 1361, 1284, 1193, 1159, 1107, 1028, 976, 858, 743; 1 H NMR (600MHz, DMSO) δ 8.04 (t, J = 7.7, 1.3 Hz, 1H, H-6'), 7.50 (d, J = 8.7 Hz, 1 H-6), 7.40-7.36 (m, 1H, H-4'), 7.33-7.27 (m, 2H, H-5', H-10), 7.26 (d, J = 2.1Hz, 1H, H-3'), 6.50 (dd, J = 8.7, 2.6 Hz, 1H, H-5), 6.48 (d, J = 2.5 Hz, 1H, H-3), 3.76 (s, 3H, OCH 3 ), 2.39 (s, 3H, CH 3 ); 13 C NMR (151 mHz, DMSO) Δ...

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Abstract

The invention discloses a paeonol thiazole derivative and a preparation method and application thereof. The paeonol thiazole derivative has a structure shown in a formula (I), wherein R is a benzene ring substituent, and in particular one of hydrogen atom, halogen atom, hydroxyl group, methoxy group and nitro group. The preparation method comprises the following steps of: A, performing condensation reaction on paeonol and thiosemicarbazide to synthesize paeonol thiosemicarbazide; and B, reacting the prepared paeonol thiosemicarbazide with alpha-bromoacetophenone of different substituents to obtain the paeonol thiazole derivative. By the adoption of the paeonol thiazole derivative and the preparation method and application thereof, a new paeonol thiazole derivative is provided, which has the advantages of short preparation period, simple operation, low cost, high purity and stable quality of the obtained derivative; and experiments also show that antitumor activity of the derivative canbe improved by introducing an antitumor pharmacodynamic group thiazole on a paeonol skeleton, and the derivative can be used as the antitumor derivative.

Description

technical field [0001] The invention relates to thiazole derivatives, in particular to paeonol thiazole derivatives, a preparation method and application thereof. Background technique [0002] Cancer is one of the most serious diseases that endanger human health today, and the incidence rate is on the rise. However, most of the current clinical anti-tumor drugs have shortcomings such as high toxicity, poor effect, and multi-drug resistance. Therefore, the research and development is efficient. New anti-tumor drugs with low toxicity are a major problem to be solved urgently. [0003] Paeonol, also known as paeonol, is the main active ingredient of traditional Chinese medicine Cortex Moutan and Xu Changqing. Pharmacological studies have shown that paeonol has antioxidant, antibacterial and anti-inflammatory, sedative and hypnotic effects, antipyretic and analgesic, immune regulation, anti-atherosclerosis, and anticoagulant and other pharmacological activities. At the same ti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/50A61P35/00
CPCC07D277/50A61P35/00
Inventor 李芳耀马献力张业黄琳庞富华王妙李倩邹登峰
Owner GUILIN PHARMA
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