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1,2,3,4-tetrahydro-beta-carboline-N-heterothioiminazole compound as well as preparation and application

A technology of heterothiimidazole and compound, which is applied in the field of pharmacy and achieves the effects of convenient post-processing, wide application range and wide substrate range

Inactive Publication Date: 2017-11-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although a series of framework structures with fluorescent properties have been found, such as coumarins, fluoresceins, rhodamines, cyanine dyes, naphthalimides, fluoropyrroles, etc., each fluorophore has Its specific fluorescent properties, but also have different shortcomings, but the application of fluorophores in molecular imaging, the demand for specific emission wavelengths, high quantum yields and related optical properties, requires the development of new types that can adjust different excitation and emission wavelengths. Fluorophores with excellent quantum yield

Method used

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  • 1,2,3,4-tetrahydro-beta-carboline-N-heterothioiminazole compound as well as preparation and application
  • 1,2,3,4-tetrahydro-beta-carboline-N-heterothioiminazole compound as well as preparation and application
  • 1,2,3,4-tetrahydro-beta-carboline-N-heterothioiminazole compound as well as preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 1-Phenyl-2,5,6,11-tetrahydro-3H-imidazo[1',5':1,2]pyrido[3,4-b]indole-3-thione

[0050]

[0051]Tryptamine (1.0mmol, 160.2mg), 2,2-dihydroxy-1-phenylethanone (1.2mmol, 182.4mg), potassium thiocyanate (2.0mmol, 194mg), trifluoroacetic acid (1.0mmol, 76 μL) was added to a high-pressure and high-temperature-resistant glass sealed tube, and then added to 5 mL of anhydrous acetonitrile. After the addition, the reaction was carried out in a 40-degree oil bath. The reaction was detected by TLC, and the reaction was completed after 8 hours. After the reaction was completed, the obtained reaction solution was concentrated, extracted with water and ethyl acetate, and the obtained organic phase was dried and concentrated to obtain a residue, which was recrystallized with ethanol to obtain a yellow solid with a yield of 80%.

[0052] Yellow solid, m.p.>250℃, 1 H NMR(500MHz,DMSO)δ12.70(s,1H),10.66(s,1H),7.70-7.66(m,2H),7.55-7.51(m,3H),7.44(t,J=7.5Hz, 1H), 7.39(d, J=8....

Embodiment 2

[0053] The yield situation comparison of this reaction of embodiment 2 under different reaction conditions

[0054]

[0055] Table 1

[0056] sequence

Embodiment 3

[0057] Example 3 1-(4-(trifluoromethyl)phenyl)-2,5,6,11-tetrahydro-3H-imidazo[1',5':1,2]pyrido[3,4 -b] indole-3-thione

[0058]

[0059] The synthesis steps are the same as in Example 1, except that 2,2-dihydroxy-1-phenylethanone is replaced by 2,2-dihydroxy-1-(p-trifluoromethylphenyl)ethanone to obtain a yellow solid, which is recovered as The rate is 77%.

[0060] Yellow solid, m.p.>250℃, 1 H NMR (500MHz, DMSO) δ12.86(s, 1H), 10.80(s, 1H), 7.86(d, J=8.0Hz, 4H), 7.55(d, J=7.9Hz, 1H), 7.39(d ,J=8.1Hz,1H),7.14(dd,J=11.1,3.9Hz,1H),7.06(t,J=7.4Hz,1H),4.15(t,J=6.7Hz,2H),3.15(t ,J=6.7Hz,2H). 13 C NMR (125MHz, DMSO) δ162.4, 155.4, 138.0, 132.6, 128.6 (q, J = 31.6Hz), 128.0, 126.5 (q, J = 3.5Hz), 126.0, 124.7 (d, J = 270Hz), 124.2, 123.1, 120.7, 120.0, 119.4, 118.7, 112.7, 111.1, 42.0, 20.0. HRMS (ESI): m / z calcd for (C 20 h 14 f 3 N 3 S+H) + :386.0933; found: 386.0934.

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Abstract

The invention discloses a 1,2,3,4-tetrahydro-beta-carboline-N-heterothioiminazole compound. The functionalized 1,2,3,4-tetrahydro-beta-carboline-N-heterothioiminazole compound is mainly synthesized by taking an alpha,alpha-dihydroxy ethanone type compound, substituted tryptamine and potassium thiocyanate through a one-pot method at 40 DEG C under an acidic condition. A preparation method provided by the invention is simple to operate and raw materials are easy to obtain; a plurality of substituent groups can be introduced simultaneously and a product is easy to separate. The 1,2,3,4-tetrahydro-beta-carboline-N-heterothioiminazole compound prepared by the preparation method has a certain optical property, can be applied to molecular imaging as a potential fluorophore and can be applied to preparation of fluorophores with fluorescent properties. A molecular formula is as follows: the molecular formula is shown in the description.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a 1,2,3,4-tetrahydro-β-carboline-N-heterothioimidazole compound, a preparation method and application. Background technique [0002] Fluorophores provide the basis for changing spectral properties, are reporters that convert recognition information into fluorescent signals, and are the basis for probe composition. Fluorophores with good optical properties are the decisive factor for probes to have excellent detection capabilities. The most important property of fluorescent probes is the ability to detect analytes in complex environments, and the sensitivity and signal-to-noise ratio of probes depend largely on the light intensity, stability, and excitation and emission wavelengths of fluorophores. [0003] Although a series of framework structures with fluorescent properties have been found, such as coumarins, fluoresceins, rhodamines, cyanine dyes, naphthalimides, fluoropyrroles, etc., eac...

Claims

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Application Information

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IPC IPC(8): C07D487/14C09K11/06
CPCC07D487/14C09K11/06C09K2211/1029C09K2211/1044
Inventor 陈文腾邵加安陈恩韩峰俞永平
Owner ZHEJIANG UNIV
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