Novel photosensitizer as well as preparation method and application thereof
A photosensitizer, a new type of technology, applied in the field of photosensitizers, can solve problems such as high oxygen dependence, and achieve the effect of outstanding universality and high-efficiency treatment
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[0044] Example 1
[0045]
[0046] (1) Synthesis of Compound I
[0047]D-biotin (300 mg, 1.23 mmol) of 10 ml of methanol suspension was added to sulfoxide (0.3 mL, 4.0 mmol), stirred at room temperature overnight until the reaction liquid clarified and transparent. The white solid was obtained under reduced pressure. It was dispersed into 10 mL of methanol and slowly dripped the hydrated sac (0.48 mL, 10 mmol) while stirring, heated to 70 ° C, and the reaction was 12 h. Cooled to room temperature, distilled under reduced pressure, poured into a large amount of ice-cold methanol, filtered, washed three times with methanol to give a white powder-shaped compound I.
[0048] (2) Compound IIIA synthesis
[0049] In a nitrogen atmosphere, Compound IIA (DCF-TFM, 20.4 mg, 0.025 mmol) was dissolved in 5 mL anhydrous DMF, 0 ° C, add 1- (3-dimethylaminopropyl) -3-ethyl carbon two Asia Amine hydrochloride (EDCI) (24 mg, 0.125 mmol), 1-hydroxybenzene triazole (HOBT) (17 mg, 0.125 mmol) and N...
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[0050] Example 2
[0051]
[0052] (1) Synthesis of Compound I as in Example 1.
[0053] (2) Synthesis of Compound IIIB
[0054] In a nitrogen atmosphere, compound IIB (Fl, 50 mg, 0.065 mmol) was dissolved in 5 ml of anhydrous DMF, and 1- (3-dimethylaminopropyl) -3-ethyl carbide hydrochloric acid was added at 0 ° C. Salt (EDCI) (62.8 mg, 0.33 mmol), 1-hydroxybenzene triazole (HOBT) (44 mg, 0.33 mmol) and N, N-diisopropylidelamine (DIEA) (32 μL, 0.2 mmol) reaction 2H After the addition, Compound I (33.5 mg, 0.13 mmol) was added, and stirred at room temperature for 24 h. Decompression distillation was purified by column chromatography (methanol / dichloromethane = 1 / 8) to obtain a photosensitizer compound IIIb. The high distortion of the compound IIIb and the nuclear magnetic resonance spectrometry table show respectively image 3 and Figure 4 Indicated.
Example Embodiment
[0055] Example 3
[0056]
[0057] (1) Synthesis of Compound I as in Example 1.
[0058] (2) Synthesis of Compound IIIC
[0059] In a nitrogen atmosphere, Compound IIC (PPIX, 30 mg, 0.053 mmol) was dissolved in 3 ml anhydrous DMF, and 1- (3-dimethylaminopropyl) -3-ethyl carbide hydrochloric acid was added at 0 ° C. Salt (EDCI) (10.56 mg, 0.053 mmol), 1-hydroxybenzene triazole (HOBT) (7.43 mg, 0.053 mmol) and N, N-diisopropylamine (DIEA) (8.75 μL, 0.053 mmol) After 2 h, Compound I (15.3 mg, 0.05 mmol) was added, and stirred at room temperature for 24 h. Decapression was purified, and the photosensitizer compound was obtained after purification using column chromatography (methanol / dichloromethane = 1 / 8). The high distortion mass spectrometry of Compound IIIC and the nuclear magnetic resonance spectrum pattern are shown. Figure 5 and Image 6 Indicated.
[0060] Figure 7 For the absorption of photosensitizer compound IIIA and compound IIA in ethanol, Figure 8 For the absorption ...
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