Probe compound for detecting Mycobacterium tuberculosis beta-lactamase, preparation method, and fluorescent probe
A technology of mycobacterium tuberculosis and lactamase, applied in the medical field, can solve the problems of low detection accuracy and sensitivity, and achieve the effects of accurate detection, improved sensitivity, and low cost
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Embodiment 1
[0067] The preparation of general formula Ⅳ compound, as attached figure 1 shown, including the following steps:
[0068] (1) Synthesis of Compound II
[0069] Compound I first undergoes a substitution reaction with NaI, and the resultant then undergoes a substitution reaction with the light-emitting structure Dye, so that the structure of the light-emitting part is connected to the cephalosporin structure in Compound I through an aromatic ether bond, so that the structure of the light-emitting part is passed through an aromatic ether. The bond is connected with the cephalosporin structure in compound I to obtain compound II;
[0070] Wherein, the light-emitting 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 follows: figure 1 shown;
[0071] (2) Synthesis of compound III
[0072] Compound II reacts with phosphorus pentachloride and pyr...
Embodiment 2
[0076] The preparation of compound 4-H, as attached figure 2 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 equiv). After stirring at room temperature for 2 hours, the substitution reaction occurred, and then the solvent was removed in vacuo. Put the crude mixture under H 2 Partition between O (100ml) and organic solvent (100ml) and separate the layers. The aqueous layer was extracted with the same organic solvent (2×100ml), then washed with 5% NaS 2 o 3 aqueous solution (100ml) and brine (100ml) to wash the combined organic layers. The organic layer was dried over desiccant, filtered, and concentrated in vacuo. The crude product was dissolved in acetonitrile (150ml), and 7-hydroxycoumarin (3.24g, 20mmol, 2eq) and potassium carbonate (5.52g, 40mmol, 4eq) were added for a substitution reaction. The reaction mixture was stirred at...
Embodiment 3
[0090] The preparation of compound 4-OMe, as attached figure 2 , attached image 3 shown, including the following steps:
[0091] (1) Repeat the operation from step (1) to step (3) in Example 2 to obtain light yellow solid compound 4-H;
[0092] (2) Under an argon atmosphere, the compound 4-H (105 mg, 0.16 mmol) was dissolved in anhydrous tetrahydrofuran (1.4 ml), the mixed solution was cooled to -78 ° C, and lithium methoxide (13 mg, 0.34 mmol) in anhydrous tetrahydrofuran (4 mL) and anhydrous methanol (0.64 ml), then tert-butyl hypochlorite (29 ml, 0.26 mmol) was added dropwise, and the mixture was stirred at the same temperature for half an hour, Compound 4-H undergoes methoxylation reaction with lithium methoxide and t-butyl hypochlorite. The reaction solution was poured into aqueous ammonium chloride solution and extracted with ethyl acetate (15ml×3). Subsequent purification by flash chromatography on a silica gel column afforded compound 4-OMe (80 mg, 73%).
[0093...
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