Bis-(p-alkoxypropiophenone) glutathione-s-transsulfase latent inhibitor
A technology of alkoxy phenylpropenone and glutathione, which is applied in the field of enzyme inhibitor drugs to achieve the effects of easy preparation, avoidance of toxicity, and low toxicity of fragments
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Embodiment 1
[0072] Embodiment 1. The synthesis of p-alkoxy propenone structural unit I
[0073] Synthesis 1: 4-acryloylphenoxyacetic acid
[0074] Scheme 1: Add phenoxyacetic acid (3.6g, 24mmol) to 100ml of dichloromethane, stir at room temperature, add anhydrous aluminum chloride powder (10g, 75mmol) in batches, then slowly add 2.5ml of acryloyl chloride (30mmol ), producing a yellow viscous substance, reacting at 30-50°C for 4 hours to obtain a reddish-brown two-phase mixture, adding 100g of ice water containing 3ml of concentrated hydrochloric acid after cooling, stirring, and extracting with dichloromethane (100ml×2), dichloromethane 5% NaHCO for methane liquid 3 Extract (50ml×2), NaHCO 3 The extract was acidified to pH 2.0 with concentrated hydrochloric acid to produce a precipitate, which was filtered and dried to obtain a crude product, which was purified by column (ethyl acetate: petroleum ether: glacial acetic acid = 1:4:0.01) to obtain 2.6 g (55%) of a white powder, m.p. 180-...
Embodiment 2
[0080] Embodiment 2. Preparation of p-alkoxypropiophenone structural unit II
[0081] Synthesis of 4-acryloylphenoxyethylamine:
[0082] The first step of synthesis of phenoxyethylamine hydrochloride
[0083] Phenol 1.9g (0.02mol), 2-chloroethylamine 8.6g (0.07mol), K 2 CO 3 186g (1.35mol), DMF (90mL) was heated to reflux. After cooling for two hours, the solid was removed by filtration, and the concentrated brown oil was dissolved in ethyl acetate, washed with water and saturated brine, dried and concentrated to obtain 2-phenoxyethylamine. The oil was dissolved in 10 ml of methanol, and then 3-5% methanolic hydrochloric acid solution (50 ml) was added, and concentrated to obtain 2.4 g of 2-phenoxyethylamine hydrochloride as a white solid, with a yield of 57%.
[0084] Preparation of the second step 4-acryloylphenoxyethylamine hydrochloride
[0085] Add 2.1g (12mmol) of 2-phenoxyethylamine hydrochloride to 0.8g (9mmol) of acryloyl chloride and 1,2-dichloroethane (40mL), c...
Embodiment 3
[0100] Example 3. Synthesis of Diethacryl Ethanolamine (C7) and Similar Diesters C22, C23, C24, C25, C26
[0101] Weigh ethacrynic acid (1.0g, 3.3mmol) and 10ml SOCl 2 Add it to a 100ml dry round bottom flask, gradually heat up to reflux for 10 hours, cool to room temperature, and remove excess SOCl by distillation under reduced pressure 2 , cooled to room temperature and dissolved in dry 10ml THF, added 0.5ml triethylamine, and slowly added dropwise 0.2ml ethanolamine and 0.5ml triethylamine that had been dissolved in 5ml THF, this process was carried out under ice bath. During the period, it was detected by thin-layer chromatography. After the reaction, it was concentrated under reduced pressure and filtered to remove THF, and an appropriate amount of dichloromethane was added for extraction. CH 2 Cl 2 layer sequentially with 5% NaHCO 3 aqueous solution, 0.5M hydrochloric acid aqueous solution and saturated brine, washed repeatedly, and dried over anhydrous sodium sulfate...
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