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A kind of biological probe of methylbenzofuran quinolines and its preparation method and application

A technology of furoquinoline and biological probes, which is applied in the field of biological probes and can solve problems such as no clear conclusions

Active Publication Date: 2016-06-29
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So whether the derivative of this structure directly acts on the G-quadruplex in that part of the region, there is no clear conclusion yet

Method used

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  • A kind of biological probe of methylbenzofuran quinolines and its preparation method and application
  • A kind of biological probe of methylbenzofuran quinolines and its preparation method and application
  • A kind of biological probe of methylbenzofuran quinolines and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Embodiment 1: the synthesis of compound 2T6

[0072] Dissolve 0.3mol of chloroacetic acid in 60ml of water, adjust the pH to 9 with sodium hydroxide, then add 0.2mol of phenol, and reflux at 100°C to obtain compound T1, then add thionyl chloride for chlorination reaction to obtain compound T2, steam Thionyl chloride solvent was removed to obtain a brown liquid, which was then condensed with anthranilic acid to obtain T3, and then PPA was preheated to 130°C and added to T3 for a compound reaction to obtain compound T4, and T4 was mixed with thionyl chloride at 80 Chlorination reaction was carried out at reflux at ℃ to obtain compound T5, and then the purified T5 was added to a single-necked bottle, and phenol was added to react overnight at 60°C, then 1,4-butanediamine was added to react at 120°C for 12 hours, and finally the product was passed through silica gel Column purification yielded compound 2T6.

[0073] Yield: 82%; Melting point: 158-159°C; 1 HNMR: (400MHz, C...

Embodiment 2

[0076] Embodiment 2: the synthesis of compound 4T7

[0077] Dissolve 0.3mol of chloroacetic acid in 60ml of water, adjust the pH to 9 with sodium hydroxide, then add 0.2mol of p-methoxyphenol, and reflux at 100°C to obtain compound T1, and then add thionyl chloride for chlorination reaction to obtain For compound T2, distill off the thionyl chloride solvent to obtain a brown liquid, then perform condensation reaction with anthranilic acid to obtain T3, then preheat PPA to 130°C and add T3 for compound reaction to obtain compound T4, and combine T4 with chlorinated Sulfoxide was refluxed at 80°C for chlorination reaction to obtain compound T5, and then the purified T5 was methylated with methyl iodide in a sulfolane solvent system to obtain compound T6, and T6-2 was added to a single-necked bottle , using ethylene glycol ether as a solvent, and reacting with N,N-bis(3-aminopropyl)methylamine at 120°C for 30 minutes, and finally adding a large amount of anhydrous ether, precipit...

Embodiment 3

[0081] Embodiment 3: the synthesis of compound 5T8

[0082] The method is the same as in Example 2, except that T5 is used as a solvent in dichloromethane, and boron tribromide is used to remove the methyl group in the methoxy group to obtain compound T6-1. React with N,N-dimethylethanolamine under anaerobic conditions, obtain compound T7-1 after purification by silica gel column, add T7-1 into a single-necked bottle, and add phenol to react overnight at 60°C, then add 1, 4-Butanediamine was reacted at 120° C. for 12 h, and finally the product was purified by silica gel column to obtain compound 5T8.

[0083] Yield: 84%; Melting point: 176-177°C; 1 HNMR: (400MHz, CDCl 3 )δ8.15(d,J=8.3Hz,1H),7.94(d,J=8.4Hz,1H),7.78(d,J=2.5Hz,1H),7.61(t,J=7.2Hz,1H) ,7.42-7.36(m,2H),7.19(dd,J=8.9,2.6Hz,1H),5.73(s,1H),4.14(t,J=5.6Hz,2H),3.99(t,J=6.5 Hz, 2H), 2.80-2.74(m, 4H), 2.34(s, 6H), 1.87-1.76(m, 2H), 1.67-1.60(m, 2H); ESI+APCI-MSm / z: 393[M +H] + .

[0084]

[0085] Compound 5T8

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Abstract

The invention discloses a benzofuran quinoline type biological probe and a preparation method thereof, and application of the benzofuran quinoline type biological probe in detecting a G-quadruplex structure and in the mechanism of action of cryptolepine and G-quadruplex, wherein the biological probe is high in fluorescence intensity and excellent in fluorescence property, and can be applied to specially detecting the G-quadruplex structure and researching the mechanism of action of a cryptolepine derivative and the G-quadruplex. The invention relates to the research whether the cryptolepine derivative acts on the telomere G-quadruplex or the C-MYCG-quadruplex in the promoter region, or on other G-quadruplex structures in vivo; the detection method has the advantages of simple, convenient and quick operation, good selectivity and obvious visualization; the shortcomings of unavailable in-vivo detection, high price, high requirement equipment, relatively complex technical operations and the like of other detection methods are overcome.

Description

technical field [0001] The present invention relates to a kind of biological probe, more specifically, to a kind of biological probe of methylbenzofuran quinolines and its preparation method and application. Background technique [0002] G-quadruplex (G-quadruplex) is a special DNA secondary structure. Many guanine-rich regions in the human genome have the ability to form this structure, including the guanine repeat at the end of the telomeric region, and the promoter regions of various genes, such as c-kit, c-myc, c-myb, bcl-2 , PDGF, kRAS, VEGF, Rb and insulin genes, etc. The latest research shows that RNA sequences in many non-coding regions can also form a G-quadruplex structure. The G-quadruplex structure of RNA is more stable than that of DNA. This structure may prevent gene translation or participate in the process of protein binding and recognition. To achieve the effect of inhibiting tumor growth. The formation of G-quadruplex structure regulates a series of phys...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C09K11/06C07F5/02C07D491/048G01N21/64G01N33/52
Inventor 黄志纾古练权杜刚花闻钊谭嘉恒
Owner SUN YAT SEN UNIV
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