Sulfydryl-containing fluorescent compound or thioester derivative thereof and preparation and application thereof
A technology of fluorescent compounds and derivatives, which is applied to the preparation of mercaptans, compounds containing elements of group 3/13 of the periodic table, fluorescence/phosphorescence, etc., can solve the problems of inapplicable NO dynamic detection and irreversible detection, and achieve good results. The effect of biomembrane permeability, excellent selectivity, and rapid detection response
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Embodiment 1
[0032] Embodiment 1: the preparation of I-1
[0033]
[0034] Compound 1a is reacted with cystamine in dry dichloromethane under the condition of peptide synthesis condensing agent (such as HBTU). After the end, add ethyl acetate to dilute, wash twice with saturated aqueous sodium bicarbonate solution, saturated aqueous ammonium chloride solution, and saturated saline, and dry the organic phase over anhydrous sodium sulfate, spin dry, and wash with methanol-containing chloroform solution (1 %-10% methanol, gradient elution) as the eluent for silica gel column chromatography purification to obtain 1b (82%), high resolution mass spectrum HRMS: 547.2113 (M+H) + .
[0035] Intermediate 1b was redissolved in methanol, dithiothreitol was dissolved in water, added to the system, and reacted at room temperature. The reaction was monitored by thin-layer chromatography. After the end, the methanol was spun off, extracted twice with dichloromethane, the organic layers were combined,...
Embodiment 2
[0036] Embodiment 2: the preparation of I-2
[0037]
[0038] Add triethylamine to compound 2a and cystamine in dry dichloromethane, and stir at room temperature. After the reaction was completed, pure water and saturated brine were added to wash twice, the organic phase was dried over anhydrous sodium sulfate, spin-dried, and purified by column chromatography to obtain 2b (93%). Mass Spectrum m / z 618.15(M+H) + .
[0039] Referring to the synthesis of compound I-1, 2b was reduced to prepare I-2 with a yield of 80%. High resolution mass spectrum 311.0935(M+H) + .
Embodiment 3
[0040] Embodiment 3: the preparation of I-3
[0041]
[0042] Compound 3a was dissolved in ethanol, added cystamine, and refluxed. After the reaction was complete, it was cooled and filtered with suction to obtain 3b as a yellow solid. Yield 60%. Mass Spectrum m / z 621.20 (M+Na) + .
[0043] Referring to the synthesis of compound I-1, I-3 was prepared by reducing 3b with a yield of 85%. High resolution mass spectrum 301.0989(M+H) + .
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