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3-Schiff base-2(1H)-quinolinone derivative and preparation method and application thereof

A quinolinone and Schiff base technology, applied in the field of medicine, can solve problems such as no public reports on quinolinone derivatives, and achieve the effects of improving electron mobility, short preparation period and high purity

Inactive Publication Date: 2013-01-16
GUILIN NORMAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many 2(1H)-quinolinone derivatives obtained by substitution at the 3-position and / or 4-position of 2(1H)-quinolinone have been reported in the existing literature, there are no such derivatives at the 3-position. Published reports on 3-Schiff base-2(1H)-quinolinone derivatives with functional Schiff bases and phenolic hydroxyl groups

Method used

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  • 3-Schiff base-2(1H)-quinolinone derivative and preparation method and application thereof
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  • 3-Schiff base-2(1H)-quinolinone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of 3-((n-butylimino)methyl)-2(1H)-quinolinone (compound 3)

[0028] Weigh 11.73g (1mmol) of the compound, 0.74g (1mmol) of n-butylamine, and 30mL of ethanol in a round-bottomed flask, and reflux at 85°C until the reaction is complete (TLC tracking detection, about 2h), after cooling, filter with suction. The filter residue was air-dried to obtain 1.89 g of compound 3 (light yellow solid), with a yield of 83%.

[0029] Compound 3 was analyzed, and its physicochemical and spectral properties were as follows:

[0030] Compound 3: Yields 83%, mp: 206~208°C; 1 H NMR (500MHz, DMSO-d 6 )δ12.04(s,1H,NH),8.54(s,1H,N=CH),8.43(s,1H,C=CH),7.82(d,J=7.7Hz,1H,Ar–H), 7.54(t,J=7.6Hz,1H,Ar–H),7.32(d,J=8.2Hz,1H,Ar–H),7.20(t,J=7.4Hz,1H,Ar–H),3.59( t,J=6.7Hz,2H,CH 2 ), 1.64–1.57 (m,2H,CH 2 ), 1.38–1.29 (m,2H,CH 2 ),0.91(t,J=7.4Hz,3H,CH 3 ); 13 C NMR (DMSO-d 6 ,125MHz)δ161.88,156.21,137.87,136.45,134.14,131.36,126.14,123.13,118.61,115.90,84.26,33.04,20.36,14....

Embodiment 2

[0033] Example 2: Preparation of 3-((n-butylimino)methyl)-6-methyl-2(1H)-quinolinone (compound 4)

[0034] Weigh 22.74g (2mmol) of compound, 1.48g (2mmol) of n-butylamine, and 50mL of ethanol in a round-bottomed flask, and react until complete at a temperature of 85°C and an ultrasonic frequency of 40kHz (TLC tracking detection, about 1h), suction filtered after cooling, and the filter residue was dried at 40° C. to obtain 3.79 g of compound 4 (light yellow solid), with a yield of 78%.

[0035] Compound 4 was analyzed, and its physicochemical and spectral properties were as follows:

[0036] Compound 4: Yields 78%, mp: 181–183°C; 1 H NMR (500MHz, DMSO-d 6 )δ11.81(s,1H,NH),8.53(s,1H,N=CH),8.34(s,1H,C=CH),7.59(s,1H,Ar–H),7.37(d,J =8.4Hz,1H,Ar–H),7.23(d,J=8.4Hz,1H,Ar–H),3.58(t,J=6.8Hz,2H,CH 2 ),2.33(s,3H,CH 3 ), 1.63–1.56 (m,2H,CH 2 ), 1.38–1.29 (m,2H,CH 2 ),0.91(t,J=7.4Hz,3H,CH 3 ); 13 C NMR (DMSO-d 6 ,125MHz)δ161.86,156.16,137.92,136.65,133.18,131.78,129.02,126.85,119.3...

Embodiment 3

[0039] Example 3: Preparation of 3-((benzylimino)methyl)-2(1H)-quinolinone (compound 5)

[0040] The method of Example 1 was repeated, except that benzylamine was used instead of n-butylamine to obtain 1.99 g of compound 5 (yellow solid).

[0041] Compound 5 was analyzed, and its physicochemical and spectral properties were as follows:

[0042] Compound 5: Yields 76%, mp: 181.3–185.8°C; 1 H NMR (500MHz, DMSO-d 6 )δ12.05(s,1H,NH),8.71(s,1H,N=CH),8.49(s,1H,C=CH),7.81(d,J=7.8Hz,1H,Ar–H), 7.54(t,J=7.7Hz,1H,Ar–H),7.38–7.31(5H,m,Ar–H),7.27(d,J=5.5Hz,1H,Ar–H),7.19(t,J =7.5Hz,1H,Ar-H),4.80(s,2H,CH 2 ); 13 C NMR (DMSO-d 6 ,125MHz)δ161.95,157.24,140.03,139.90,137.30,131.95,129.82,128.86,128.57,127.40,127.28,126.87,126.83,122.73,119.36,115.51,64.92. + .

[0043] Therefore, it can be determined that compound 5 is 3-((benzylimino)methyl)-2(1H)-quinolinone, and its structural formula is as follows:

[0044]

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Abstract

The invention discloses a 3-Schiff base-2(1H)-quinolinone derivative and a preparation method and application thereof. The 3-Schiff base-2(1H)-quinolinone derivative is prepared by disposing 3-formaldehyde base-2(1H)-quinolinone or 3-formaldehyde base-6 methyl-2(1H)-quinolinone, primary-amine-contained compound and organic solvent into a reactor and condensing at the temperature of 80-100 DEG C. Compared with antioxidant activity of the 3-formaldehyde base-2(1H)-quinolinone or the 3-formaldehyde base-6 methyl-2(1H)-quinolinone, the antioxidant activity of the 3-Schiff base-2(1H)-quinolinone derivative is enhanced obviously. The structural formula thereof is shown as the formula (I), wherein the R1 is H or methyl, and the R2 is aromatics substituent or aliphatic hydrocarbon substituent.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to 3-Schiff base-2(1H)-quinolinone derivatives and their preparation methods and applications. Background technique [0002] 2(1H)-Quinolinone derivatives are a class of alkaloids widely present in nature, which have important anti-cancer, anti-inflammatory, anti-allergic activities (DeRuiter, J.Brubaker, A.N.; Whitmer, W.L.; Stein, J.L. ; J. Med. Chem. 1986, 29, 2024.; Hewawasam, P.; Fan, W.; Knipe, J.; . Lett. 2002, 12, 1779.; Rousell l, J.; Haddad, E.B.; Mak, J.C.; Webb, B.L.; V.O.Benzuglyi, A.P.Sidorenko, V.L.; Farm.Zh.2000,1,75.), as a combination of poly(ADP-ribose) polymerase inhibitor and anticancer agent, smooth muscle cell proliferation inhibitor and treatment of hepatitis B drug. Although many 2(1H)-quinolinone derivatives obtained by substitution at the 3-position and / or 4-position of 2(1H)-quinolinone have been reported in the existing literature, there are no such ...

Claims

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Application Information

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IPC IPC(8): C07D215/227C07D401/12A61K31/635A61K31/4709A61K31/4704A61P39/06
Inventor 张业义祥辉方毅林刘贤贤
Owner GUILIN NORMAL COLLEGE
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