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5-(tetrasubstituted alkenyl)-3, 5-dihydro-4H-imidazole-3-ketone derivative and synthesis method and application thereof

A technology for derivatives of tetrasubstituted alkenes and ketones, which can be used in the fields of drug combination, organic chemistry, antineoplastic drugs, etc., and can solve problems such as lack, difficulty in cis-trans control, and difficulty in synthesis

Active Publication Date: 2019-05-24
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the reported methods, the substituents of the exocyclic double bond formed at the 5-position are often subject to great restrictions. Generally, it is a three-substituted terminal double bond. When forming a four-substituted double bond, its cis-trans control is very difficult.
Therefore, it is difficult to synthesize 5-alkenyl-3,5-dihydro-4H-imidazol-3-one derivatives containing four-substituted double bonds, and lacks 5-alkenyl-3,5- Study on the activity of dihydro-4H-imidazol-3-one derivatives

Method used

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  • 5-(tetrasubstituted alkenyl)-3, 5-dihydro-4H-imidazole-3-ketone derivative and synthesis method and application thereof
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  • 5-(tetrasubstituted alkenyl)-3, 5-dihydro-4H-imidazole-3-ketone derivative and synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1: the synthesis of compound 3a

[0065]

[0066] Compound 1a (1.0mmol), benzenesulfonamide 2a (1mmol), K 2 CO 3 (1mmol) in DMF (2mL) at 120 ℃ for 30 minutes, after adding water and extracting with ethyl acetate, the organic phases were combined, washed with water and dried, concentrated, and column chromatography gave compound 3a as a white solid (307mg, 70% yield ): 1 H NMR (400MHz, CDCl 3 )δ11.21(s,1H),9.72(s,1H),7.54-7.62(m,3H),7.42-7.47(m,7H),5.17(s,1H),3.12(s,3H),1.13 (s,9H); 13 C NMR (100MHz, CDCl 3)δ203.5,153.8,152.5,138.7,133.3,130.8,130.7,129.5,129.0,128.9,128.8,127.7,116.2,75.8,41.9,27.6,25.8; ESI-MS m / z 440.1(M+H + ).

Embodiment 2

[0067] Embodiment 2: the synthesis of compound 3b

[0068]

[0069] Compound 1a (1.0mmol), p-trifluoromethylbenzenesulfonamide 2b (1mmol), K 2 CO 3 (0.5mmol) in DMSO (2mL) at 120 ° C for 50 minutes after stirring and reacting, adding water and extracting with ethyl acetate, combining the organic phases, washing with water and drying, concentrating, and column chromatography to give compound 3b as a white solid (431mg, 85% yield): 1 H NMR (400MHz, CDCl 3 )δ11.24(s,1H),9.72(s,1H),7.65-7.74(m,4H),7.40-7.47(m,5H),5.18(s,1H),3.10(s,3H),1.10 (s,9H); 13 C NMR (100MHz, CDCl 3 )δESI-MS m / z 508.1 (M+H + ).

Embodiment 3

[0070] Embodiment 3: the synthesis of compound 3c

[0071]

[0072] Compound 1a (1.0mmol), p-methoxybenzenesulfonamide 2c (1mmol), Cs 2 CO 3 (1mmol) in DMSO (2mL) at 120 ℃ for 30 minutes, after adding water and extracting with ethyl acetate, the organic phases were combined, washed with water and dried, concentrated, and column chromatography gave compound 3c as a white solid (329mg, 70% yield ): 1 H NMR (400MHz, CDCl 3 )δ11.21(s,1H),9.63(s,1H),7.41-7.49(m,7H),6.84(d,J=8.8Hz,2H),5.15(s,1H),3.83(s,3H ),3.09(s,3H),1.10(s,9H); 13 C NMR (100MHz, CDCl 3 )δ203.3,163.7,163.1,152.4,130.8,130.6,130.1,129.7,129.0,128.8,115.9,113.9,75.6,55.5,41.8,27.5,25.7; ESI-MS m / z 470.1(M+H + ).

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Abstract

The invention relates to a 5-(tetrasubstituted alkenyl)-3, 5-dihydro-4H-imidazole-3-ketone derivative and a synthesis method and application thereof. According to the invention, compounds with an N-(isoxazole-3-base)-amide structure or an N-(1, 2, 4-oxa-diazole-3-base)-amide structure are used as raw materials, the raw materials react with a nucleophile under an alkaline condition, by carrying outMichael addition action and Boulton-Katritzky similar rearrangement reaction on the amide through the nucleophile, the 5-(tetrasubstituted alkenyl)-3, 5-dihydro-4H-imidazole-3-ketone derivative is directly generated. The method has wide substrate applicability, simple and efficient preparation method and good functional group compatibility. The 5-(tetrasubstituted alkenyl)-3, 5-dihydro-4H-imidazole-3-ketone derivative has anti-tumor activity and wide application prospect.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and drug development, in particular to a 5-(tetrasubstituted alkenyl)-3,5-dihydro-4H-imidazol-3-one derivative and its synthesis method and application. Background technique [0002] 5-alkenyl-3,5-dihydro-4H-imidazol-3-one derivatives are key structures in many natural products and compounds with important biological activities, exhibiting a wide range of biological activities (Ermoli, A. et al J. Med. Chem. 2009, 52, 4380-4390; Gadwood, R. et al J. Med. Chem. 1993, 36, 1480-1487.). At the same time, this type of structure is also a key fragment of histidine ammonia-lyase in vivo (Sànchez-Murcia, P.A. et al Biochemistry 2016, 55, 5854-5864). [0003] There are not many methods for synthesizing 5-alkenyl-3,5-dihydro-4H-imidazol-3-one structure reported in the literature, and the reaction of imidazolone with aldehyde or imine is usually used to form an extracyclic double bond at the 5-position (...

Claims

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Application Information

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IPC IPC(8): C07D233/96C07D401/12C07D409/12A61P35/02
Inventor 蔡倩拉金德拉普拉萨德·科塔吉里
Owner JINAN UNIVERSITY
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