Probe compound for detecting mycobacterium tuberculosis beta-lactamase, preparation method and fluorescent probe
A technology of mycobacterium tuberculosis and lactamase, which is applied in the medical field, can solve the problems of low detection accuracy and sensitivity, and achieve the effect of reducing background noise signals
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Embodiment 1
[0067] Preparation of compounds of general formula IV, as attached figure 1 As shown, including the following steps:
[0068] (1) Synthesis of compound II
[0069] Compound I first undergoes substitution reaction with NaI, and the resultant undergoes substitution reaction with the light-emitting structure Dye to connect the structure of the light-emitting part with the cephalosporin structure of compound I through the aromatic ether bond, so as to connect the structure of the light-emitting part through the aromatic ether The bond is connected with the cephalosporin structure in compound I to prepare compound II;
[0070] Among them, the luminescent structure Dye is selected from any one of fluorescein isothiocyanate, phycoerythrin, AlexaFluor series dyes, and Tokyo green; the structural formulas of compound I and compound II are as attached figure 1 Shown
[0071] (2) Synthesis of compound III
[0072] Compound II undergoes deacylation and deprotection reaction with phosphorus pentach...
Embodiment 2
[0076] Preparation of compound 4-H, as attached figure 2 As shown, including the following steps:
[0077] (1) Preparation of compound 2
[0078] To a suspension of compound 1 (4.86 g, 10 mmol) and acetone (110 mL) was added NaI (15 g, 100 mmol, 10 equivalents). After stirring for 2 hours at room temperature, a substitution reaction occurred, and then the solvent was removed in vacuum. Place the crude mixture in H 2 Partition between O (100ml) and organic solvent (100ml) and separate the layers. Extract the water layer with the same organic solvent (2×100ml), then use 5% NaS 2 O 3 The combined organic layer was washed with aqueous solution (100ml) and brine (100ml). The organic layer was dried with a desiccant, filtered, and concentrated in vacuo. The crude product was dissolved in acetonitrile (150ml), 7-hydroxycoumarin (3.24g, 20mmol, 2eq) and potassium carbonate (5.52g, 40mmol, 4eq) were added, and substitution reaction occurred. The reaction mixture was stirred for 12 hour...
Embodiment 3
[0090] Preparation of compound 4-OMe, as attached figure 2 , Attached image 3 As shown, including the following steps:
[0091] (1) Repeat the operations from step (1) to step (3) in Example 2 to prepare a pale yellow solid compound 4-H;
[0092] (2) Under an argon atmosphere, compound 4-H (105mg, 0.16 mmol) was dissolved in anhydrous tetrahydrofuran (1.4ml), the mixed solution was cooled to -78°C, and lithium methoxide (13mg, 0.34 Millimoles) in anhydrous tetrahydrofuran (4mL) and anhydrous methanol (0.64ml), then tert-butyl hypochlorite (29ml, 0.26mmol) was added dropwise, and the mixture was stirred at the same temperature for half an hour, Compound 4-H undergoes a methoxylation reaction with lithium methoxide and tert-butyl hypochlorite. The reaction solution was poured into an aqueous ammonium chloride solution and extracted with ethyl acetate (15 ml×3). Follow-up purification by flash chromatography on silica gel column gave compound 4-OMe (80 mg, 73%).
[0093] Structural...
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