Porphyrin derivative and application for the same as small molecule antioxidant
A derivative, porphyrin technology, applied in a class of porphyrin derivatives and its application as a small molecule antioxidant, can solve the problems of limiting drug feasibility, high cost, and inability to enter cells
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Embodiment 1
[0033] Embodiment 1: the preparation of 3-(2-methoxyethoxy) benzaldehyde
[0034]
[0035] Dissolve 100 grams of m-hydroxybenzaldehyde in 1 liter of DMF, add 226 grams of anhydrous potassium carbonate, stir for 30 minutes, add 81.3 grams of 2-chloroethyl methyl ether, heat and reflux for 6 hours, evaporate DMF under reduced pressure, add Dissolve in 500 ml of water, filter, extract the filtrate 3 times with dichloromethane, combine the extracts, wash with 200 ml of 2% sodium hydroxide solution, wash with water 3 times, dry over anhydrous sodium sulfate, filter, evaporate the solvent, 154 g of product were obtained. ESI-MS: [M+H] + , 181; 1 H NMR (DMSO-d 6 ): δ3.31(s, 3H), 3.67(t, J=4.56Hz, 2H), 4.17(t, J=4.56Hz, 2H), 7.30(m, 1H), 7.43(m, 1H), 7.51 (m, 2H), 9.97(s, 1H).
Embodiment 2
[0036] Embodiment 2: the preparation of methoxyethyl p-toluenesulfonate
[0037]
[0038] Cool the mixture of 38 grams of ethylene glycol monomethyl ether and 120 grams of anhydrous pyridine to -6°C in an ice bath, add 101 grams of p-toluenesulfonyl chloride in batches, control the temperature not to exceed 0°C, and continue stirring for 30 minutes after the addition , remove the ice bath, and react at room temperature for 4 hours. The reaction mixture was slowly poured into a mixture of 250 ml of hydrochloric acid and 700 g of ice, stirred for 20 minutes, extracted 3 times with ethyl acetate, combined extracts, washed with water 3 times, dried over anhydrous sodium sulfate, and distilled off ethyl acetate to obtain 84 grams of product.
Embodiment 3
[0039] Embodiment 3: the preparation of 3-(2-methoxyethoxy) benzaldehyde
[0040]
[0041] Dissolve 12 grams of m-hydroxybenzaldehyde in 150 milliliters of DMF, add 27.6 grams of anhydrous potassium carbonate, stir, add 23 grams of methoxyethyl p-toluenesulfonate, heat and reflux for 3 hours, and evaporate DMF under reduced pressure , add 200 milliliters of water to dissolve, extract 3 times with dichloromethane, combine the extracts, wash with 200 milliliters of 5% sodium hydroxide solution, wash with water 3 times, dry over anhydrous sodium sulfate, filter, and distill off the solvent to obtain 16 grams of product.
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