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2,9-bisstyrene-substituted o-phenanthroline compounds, preparation method and application thereof

A compound and unsubstituted technology, applied in the field of medicine, can solve the problems of low G-quadruplex selectivity, insignificant changes in optical properties, and inability to detect with G-quadruplex structure

Active Publication Date: 2017-01-25
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the compounds have low selectivity to G-quadruplexes, and can bind to single- and double-stranded nucleic acids at the same time [T.Ou et al.ChemMedChem2008,3,690-713]
In addition, the optical properties of most compounds do not change significantly after binding to the G-quadruplex, so they cannot be used for the detection of the G-quadruplex structure

Method used

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  • 2,9-bisstyrene-substituted o-phenanthroline compounds, preparation method and application thereof
  • 2,9-bisstyrene-substituted o-phenanthroline compounds, preparation method and application thereof
  • 2,9-bisstyrene-substituted o-phenanthroline compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1, the synthesis of compound E1

[0073] 4-(4-Methylpiperazine) benzaldehyde (purchased from Bailingwei) (2.04g, 10mmol) and 2,9-dimethyl-2,9-phenanthroline (purchased from Bailingwei) (1.04g, 5mmol) was dissolved in dry toluene (10mL), reacted at a temperature of 120°C for 24 hours, and the solvent in the system was spin-dried to obtain a crude product, which was purified by silica gel column chromatography with dichloromethane as an eluent to obtain 975mg of The solid is compound E1, and the yield is 35%.

[0074] The confirmed data of the compound structure are:

[0075] 1 H NMR (CDCl 3 ,400MHz):δ(ppm):8.04(d,2H),7.95(d,2H),7.83(m,4H),7.64(d,4H),7.42(d,2H),7.02(d,2H) ,6.85(m,2H),3.34(t,8H),2.85(d,8H),2.87(s,6H). 13 C NMR (CDCl 3 ,400MHz): δ(ppm): 156.71, 151.24, 145.84, 136.25, 133.84, 128.45, 127.85, 127.06, 125.50, 120.02, 115.51, 54.95, 48.32, 46.13. HRMS (ESI-TOF) calcd for C 38 h 41 N 6 [M] + 581.3387,found 581.3386.

Embodiment 2

[0076] Embodiment 2, the synthesis of compound E2

[0077] Basically identical with embodiment 1, difference is to replace 4-(4-methylpiperazine) benzaldehyde with compound 4-(4-(2-hydroxyethyl) piperazine) benzaldehyde (purchased from Bailingwei), Reaction at 120°C for 24 hours, rotary evaporation of toluene to obtain a crude product, which was separated by silica gel column chromatography using ethyl acetate as eluent to obtain compound E2. Yield: 38%.

[0078] The confirmed data of the compound structure are:

[0079] 1 H NMR (CDCl 3 ,400MHz):δ(ppm):8.04(d,2H),7.95(d,2H),7.83(m,4H),7.64(d,4H),7.42(d,2H),7.02(d,2H) ,6.85(m,2H),3.65(s,2H),3.34(m,20H),2.53(t,4H). 13 C NMR (CDCl 3 ,400MHz): δ(ppm): 156.71, 151.24, 145.84, 136.25, 133.84, 128.45, 127.85, 127.06, 125.50, 120.02, 115.51, 59.41, 56.32, 51.33. HRMS (ESI-TOF) calcd for C 40 h 44 N 6 o 2 [M] + 640.3526,found 640.3528.

Embodiment 3

[0080] Embodiment 3: the synthesis of compound E3

[0081] Basically the same as Example 1, the difference is to replace 4-(4-methylpiperazine) benzaldehyde with compound 4-(4-morpholine) benzaldehyde (purchased from Bailingwei), react at 120 ° C for 24 hours, and rotate Toluene was evaporated to obtain a crude product, which was subjected to silica gel column chromatography with ethyl acetate as eluent to obtain compound E3. Yield: 42%.

[0082] The confirmed data of the compound structure are:

[0083] 1H NMR (CDCl 3 ,400MHz):δ(ppm):8.04(d,2H),7.95(d,2H),7.83(m,4H),7.64(d,4H),7.42(d,2H),7.02(d,2H) ,6.85(m,2H),3.65(t,8H),3.18(t,8H). 13 C NMR (CDCl 3 ,400MHz): δ(ppm): 156.71, 151.24, 145.84, 136.25, 133.84, 128.45, 127.85, 127.06, 125.50, 120.02, 115.51, 66.35, 54.62. HRMS (ESI-TOF) calcd for C 36 h 34 N 4 o 2 [M] + 554.2682,found 554.2679.

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Abstract

The invention provides 2,9-bis-styryl substituted phenanthroline compounds specifically combined with G-tetrastrobila-structure nucleic acid and a preparation method thereof, and application of the 2,9-bis-styryl substituted phenanthroline compounds in tumor resistance. The structural formula is disclosed as Formula I. The compounds disclosed as Formula I can quickly judge whether the sample to be detected is G-tetrastrobila-structure nucleic acid by ultraviolet-visible absorption spectrum or fluorescence spectrum. The drug effect test proves that the compounds disclosed as Formula I in vitro have strong inhibiting actions on multiple tumor cell strains. The 2,9-bis-styryl substituted phenanthroline compounds can be used for preparing anticancer drugs.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to 2,9-bisstyrene substituted o-phenanthroline compounds and a preparation method and application thereof. Background technique [0002] G-quadruplex (G-quadruplex) is a nucleic acid sequence rich in guanine (G), through the formation of Hoogsteen base pairing between chains or corresponding G bases in the chain, so that four or four pieces of G-rich nucleic acid A special nucleic acid secondary structure formed by aggregation of fragments [S.Burge et al.Nucleic Acids Res,2006,34,5402-5415]. G-rich sequences are ubiquitous in genomes with important functions, such as telomeres, gene promoter regions, immunoglobulin switch regions, etc. [J.L.Huppert et al.Nucleic Acids Res,2005,33,2908-2916; 2007,35,406- 413; A.K. Todd et al. Nucleic Acids Res, 2005, 33, 2901-2907]. And it is closely related to the formation mechanism of human lifespan, cancer, HIV and other diseases [T.A.Brooks...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06A61K31/496A61K31/4745A61P35/00C12Q1/68G01N21/64
CPCC07D471/04C09K11/06C09K2211/1033C09K2211/1044C12Q1/68G01N21/6428C12Q2563/107
Inventor 上官棣华刘祥军吴尚荣王林林
Owner INST OF CHEM CHINESE ACAD OF SCI
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