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Synthesis of 5-phenyl-2-o-methylphenyl-2H-1, 2, 3-triazole-rhodamine B derivate and application thereof

A technology of -2H-1 and o-tolyl, which is applied in the direction of instruments, analytical materials, luminescent materials, etc., can solve the problems of no probes and achieve high detection sensitivity

Active Publication Date: 2018-12-28
HAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorescent probes based on 1,2,3-triazole-rhodamine have been reported, but there is no report on the application of this series of probes in cell imaging

Method used

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  • Synthesis of 5-phenyl-2-o-methylphenyl-2H-1, 2, 3-triazole-rhodamine B derivate and application thereof
  • Synthesis of 5-phenyl-2-o-methylphenyl-2H-1, 2, 3-triazole-rhodamine B derivate and application thereof
  • Synthesis of 5-phenyl-2-o-methylphenyl-2H-1, 2, 3-triazole-rhodamine B derivate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Compound 1 (1.0 mmol) and compound 2 (0.8 mmol) were dissolved in CH 2 Cl 2 (12mL), add Fe(acac) at room temperature 3 (0.05mmol) and Et 3 N (0.5mL), stirred and reacted for 24 hours, TLC detected that the raw materials disappeared completely, and after the reaction liquid was concentrated, silica gel column chromatography (200-300 mesh silica gel) was carried out, and petroleum ether / ethyl acetate (V:V=3:1 ~4:1) was used as the eluent to obtain 632 mg of the compound of formula I with a yield of 88.0%. like figure 1 Shown: 1 H NMR (400MHz, CDCl 3 )δ8.04(s,1H),7.99(d,J=6.9Hz,1H),7.94–7.85(m,2H),7.61(d,J=7.5Hz,1H),7.55–7.44(m,3H ),7.36–7.28(m,5H),7.17(d,J=7.1Hz,1H),6.75(s,1H),6.73(s,1H),6.34(s,3H),6.33(s,1H) ,3.32(dd,J=13.8,6.8Hz,8H),2.37(s,3H),1.13(t,J=7.0Hz,12H); 13 C NMR (100MHz, CDCl 3 )δ164.96,158.35,153.80,151.33,149.13,148.98,138.81,136.97,133.13,132.63,131.79,129.40,129.29,129.23,129.09,128.99,128.91,128.31,128.04,126.62,125.04,124.11,123.53,108.06,104.4...

Embodiment 2

[0020] Compound 1 (1.0 mmol) and compound 2 (1.0 mmol) were dissolved in CH 2 Cl 2 (15mL), add Fe(acac) at room temperature 3 (0.08mmol) and Et 3 N (0.6mL), stirred and reacted for 20 hours, TLC detected that the raw materials disappeared completely, and after the reaction liquid was concentrated, silica gel column chromatography (200-300 mesh silica gel) was carried out, and petroleum ether / ethyl acetate (V:V=3:1 ~4:1) was used as the eluent to obtain 640 mg of the compound of formula I with a yield of 89.2%.

Embodiment 3

[0022] Compound 1 (1.0 mmol) and compound 2 (1.0 mmol) were dissolved in CH 2 Cl 2 (15mL), add Et at room temperature 3 N (0.6 mL), after stirring and reacting for 20 hours, TLC showed that except for compounds 1 and 2, no new spots were generated (ie, no reaction occurred).

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Abstract

The invention relates to synthesis of a 5-phenyl-2-o-methylphenyl-2H-1, 2, 3-triazole-rhodamine B derivate and application thereof. The derivate has the structure as shown in formula I. The derivate is applicable to HeLa cell imaging. The formula refers to the description.

Description

technical field [0001] The invention belongs to the field of organic synthesis and cell imaging, and specifically relates to the synthesis and application of a 5-phenyl-2-o-tolyl-2H-1,2,3-triazole-rhodamine B derivative. Background technique [0002] With the rapid development of industry, while bringing economic effects, the pollution it brings poses a great threat to the environment. The heavy metal ion Hg 2+ pollution cannot be ignored. Mercury, as one of the most poisonous heavy metal ions, is discharged into the soil or water body, enriching life through the food chain and posing a threat, thus causing various diseases such as Alzheimer's disease, Minamata disease, extremity pain, Uremia has seriously affected people's lives. Fluorescent probes based on 1,2,3-triazole-rhodamine have been reported, but there is no report on the application of this series of probes to cell imaging. The invention provides a one-step method for preparing highly sensitive Hg by rhodamine...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1059C09K2211/1088G01N21/6428
Inventor 何文英吴禄勇李建玲刘艳萍冯华杰丁国华
Owner HAINAN NORMAL UNIV