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N, n-dipentane substituted quinacridone compounds, preparation method and application thereof

A technology for compounds and identification methods, applied in the field of medicine, can solve problems such as limitations, and achieve the effects of real-time on-the-spot detection, low cost, and easy storage.

Active Publication Date: 2017-04-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although DNA small molecule ligands with different advantages have been widely reported, their application in vivo is limited by many factors, such as cell membrane fusion and cell-specific localization.

Method used

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  • N, n-dipentane substituted quinacridone compounds, preparation method and application thereof
  • N, n-dipentane substituted quinacridone compounds, preparation method and application thereof
  • N, n-dipentane substituted quinacridone compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1, the synthesis of compound E1 (QAB)

[0066] Dissolve NaH (200mg, 60%) and quinacridone (624mg, 2mmol) in dry THF (10mL), heat to reflux for 1h, add 5mg of tetrabutylammonium bromide, 1,5 di Pentyl bromide (2.04 g, 10 mmol) was refluxed overnight. Post-treatment: After the reaction solution was allowed to cool, 5 mL of methanol was added to quench the reaction. After the solvent was evaporated, solid column chromatography was used for separation (washing away impurities with dichloromethane of 2 times the column volume, and then using dichloromethane with a volume ratio of 1:1) Eluted with methanol and collected the eluate) to obtain compound E1. The yield was 41%.

[0067] The confirmed data of the compound structure are: 1 H NMR (300MHz, CDCl 3 ): δ (ppm) 8.72 (d, J = 9.0Hz, 2H), 8.55 (dd, J = 1.8Hz, J = 8.1Hz, 2H), 7.78-7.72 (m, 2H), 7.48 (d, J = 8.7Hz, 2H), 7.27(t, J=7.5Hz, 3H), 4.52(t, J=7.8Hz, 4H), 3.49(t, J=6.6Hz, 4H), 2.10-1.99(m, 8H) ,1.85-1....

Embodiment 2

[0068] Embodiment 2, the synthesis of compound E2 (QAP)

[0069] Basically the same as Example 1, except that 10 mmol of compound 1-(5-bromopentyl)-4-methylpiperazine was used instead of 1,5-dibromopentane, and the reaction was refluxed overnight. After evaporating the solvent, solid column chromatography (first wash away impurities with 2 times column volume of dichloromethane, then elute with dichloromethane and methanol at a volume ratio of 1:1, and collect the eluent) to obtain compound E2, The yield was 71%.

[0070] The confirmed data of the compound structure are: 1 H NMR (300MHz, CDCl 3 ): δ (ppm) 8.73 (s, 2H), 8.55 (dd, J = 1.2Hz, J = 8.1Hz, 2H), 7.76-7.71 (m, 2H), 7.48 (d, J = 8.7Hz, 2H) ,7.26(t,J=7.5Hz,3H),4.50(t,J=7.8Hz,4H),2.47-2.39(m,18H),2.29(s,7H),2.02(s,7H),1.65( t,J=3.3Hz,8H); 13 C NMR (100MHz, CDCl 3 ):δ(ppm)177.8,142.0,135.4,134.5,127.9,126.0,120.9,120.8,114.6,113.3,58.3,55.0,53.0,46.1,45.9,26.9,26.5,24.9.ESI HRMS exact masscalcd.for C 40 h 53 o 2 ...

Embodiment 3

[0071] Embodiment 3, the synthesis of compound E3 (QAT)

[0072] It is basically the same as Example 1, except that 10 mmol of the compound 5-bromo-N,N-dimethylpentanyl-1-amine is used instead of 1,5 dibromopentane, the reaction is refluxed overnight, and the solvent is evaporated Afterwards, solid column chromatography separation (first wash away impurities with dichloromethane of 2 times of column volume, then elute with volume ratio 1:1 dichloromethane and methanol, collect eluent), obtain compound E3, yield is 42%.

[0073] The confirmed data of the compound structure are: 1 H NMR (300MHz, CDCl 3 ): δ (ppm) 8.72 (s, 2H), 8.54 (dd, J = 1.2Hz, J = 7.8Hz, 2H), 7.75-7.70 (m, 2H), 7.48 (d, J = 9.0Hz, 2H) ,7.27-7.22(m,3H),4.50(t,J=7.8Hz,4H),2.36(t,J=6.3Hz,4H),2.25(t,J=2.4Hz,15H),2.03(d, J=8.1Hz, 4H), 1.65(s, 8H); 13 C NMR (100MHz, CDCl 3 ): δ (ppm) 178.0, 142.1, 135.5, 134.6, 128.0, 126.1, 121.0, 120.8, 114.6, 113.4, 59.7, 46.3, 45.6, 27.5, 27.1, 24.9.ESI HRMS exact massca...

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Abstract

The invention discloses an N, N-dipentane substituted quinacridone compound specifically combined with a nucleic acid as well as a preparation method and an application in anti-tumor. The structure formula is shown in formula I. The N, N-dipentane substituted quinacridone compound shown in formula I can rapidly judge whether the sample to be tested is a nucleic acid through a fluorescence spectrum. Under a light condition, the N, N-dipentane substituted quinacridone compound shown in formula I has a high activity for killing the tumor cell or causing the tumor cell apoptosis and has a potential as a photochemical anti-tumor therapeutic agent. The compound in formula I is easy to synthesize, stable and convenient to store.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to N,N-dipentane-substituted quinacridone compounds specifically binding to nucleic acids, a preparation method thereof, and an antitumor application thereof. Background technique [0002] Small molecules that bind to nucleic acids are widely used in nucleic acid analysis, fluorescence imaging of nucleic acids in cells, and treatment of cancer and viral infections [K.Cheung-Ong, G.Giaever and C.Nislow, Chem.Biol., 2013, 20, 648-659; K. Gurova, Future Oncology, 2009, 5, 1685-1704; L.J. Kricka, Ann. Clin. Biochem., 2002, 39, 114-129; R. Palchaudhuri and P.J. Hergenrother, Curr. Opin. Biotechnol., 2007 , 18, 497-503.]. Today, most chemotherapeutic agents are DNA-binding drugs [B. Maji and S. Bhattacharya, Chem. Commun., 2014, 50, 6422-6438.]. The binding methods of ligands and DNA include planar stacking of conjugated aromatic macrocycles, hydrogen bonds, electrostatic interaction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/4745A61K41/00A61P35/00G01N21/64C12Q1/68
CPCA61K41/0057C07D471/04C12Q1/68G01N21/6428
Inventor 上官棣华柳影刘祥军王林林
Owner INST OF CHEM CHINESE ACAD OF SCI
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