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Synthesis and application of unsymmetrical bissulfonamide compounds
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A bis-sulfonamide and compound technology, applied in the field of synthesis of asymmetric bis-sulfonamide compounds, can solve problems such as limitations
Active Publication Date: 2019-02-26
TAIZHOU UNIV
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Problems solved by technology
However, most of the reported fluorescent probes cannot selectively distinguish the three thiol-containing amino acids such as Cys, Hcy, and GSH, which greatly limits their practical application.
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Embodiment 1
[0020] Under the protection of nitrogen, accurately weigh piperazine III (189mg, 2.20mmol) and triethylamine (222mg, 2.20mmol), dissolve them in 10mL of dichloromethane, and then use a constant-pressure dropping funnel to add red to the mixture. 10 mL of a dichloromethane solution of acid chloride II (269 mg, 1.00 mmol) was added dropwise while stirring. After the dropwise addition was completed, the stirring was continued for 1 hour. TLC detected that the reaction was complete, the reaction was stopped, the solvent was distilled off under reduced pressure, and column chromatography was used for separation and purification to obtain 304 mg of a light green product (Compound IV) with a yield of 95.5%. 1 H NMR(400MHz, CDCl 3 )δ8.56(d,J=8.0Hz,1H), 8.43(d,J=8.0Hz,1H), 8.19(d,J=4.0Hz,1H), 7.53(t,J=8.0Hz,2H) ,7.18(t,J=8.0Hz,1H),3.15(t,J=8.0Hz,4H),2.86-2.88(m,10H); 13 C NMR(100MHz, CDCl 3 )δ151.7, 132.5, 130.7, 130.6, 130.5, 130.1, 128.0, 123.2, 119.8, 115.2, 46.4, 45.5, 45.4.
Embodiment 2
[0022] Under the protection of nitrogen, accurately weigh compound IV (200mg, 0.63mmol) and triethylamine (76mg, 0.75mmol), dissolve them in 10mL of dichloromethane, and then use a constant pressuredropping funnel to add compound V to the mixed solution. (155mg, 0.63mmol) of dichloromethane solution 10mL, stirring while dropping, continue to stir and react for 1 hour after the addition is complete. TLC detected that the reaction was complete, the reaction was stopped, the solvent was distilled off under reduced pressure, and column chromatography was used for separation and purification to obtain 323 mg of a yellow product (compound I) with a yield of 96%. 1 H NMR(400MHz, CDCl 3 )δ8.50(d,J=8.0Hz,1H), 8.15(d,J=8.0Hz,1H), 8.08(d,J=8.0Hz,1H),7.98(d,J=4.0Hz,1H) ,7.89(d,J=4.0Hz,1H), 7.64(t,J=8.0Hz,1H), 7.55(t,J=8.0Hz,1H), 7.23(d,J=4.0Hz,1H), 3.24 (s,8H),2.83(s,6H); 13 C NMR(100MHz, CDCl 3 )δ151.9,149.5,146.4,136.7,133.3,131.0,130.9,130.2,129.8,129.6,128.7,126.7,124.6,124.1,119.1,11...
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Abstract
The invention relates to synthesis and application of an asymmetric disulfamide compound. The asymmetric disulfamide compound is a compound of formula (I) (see details in the specification). Tests show that the ultraviolet absorption spectrum of the asymmetric disulfamide compound reacted with cysteine (Cys) has red shift of 100nm, fluorescence at 577nm can be remarkably improved, at the same time, the fluorescence of a solution can be turned yellow from blue, and other amino acids and sulfur-containing compounds are barely affected. In addition, results of response tests in different pH valuesolutions show that Cys can be selectively detected by using the compound within a pH value range of 5-12. Therefore, the compound provided by the invention can be used as a fluorescent probe for detecting Cys.
Description
Technical field [0001] The invention relates to the synthesis and application of an asymmetric bissulfonamide compound. Background technique [0002] Cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) are all intracellularly active sulfhydryl amino acids, which are involved in a variety of biochemical effects such as intracellularbiocatalysis, transcription modification, and detoxification. , Plays an extremely important role in the physiological and pathological processes of living organisms. When the intracellular Cys is lacking, it will cause many complications, such as slow growth in children, liver damage, edema, skin aging, etc.; when the Cys content is too high, it will cause Alzheimer’s, rheumatoid arthritis, Parkinson’s syndrome, etc. Series of physiological diseases. Therefore, effective detection or monitoring of Cys in biological samples or environmental samples has become a research hotspot in related fields in recent years. [0003] The traditional meth...
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