Thiochroman compound and its synthesis method and the application of preparing antifungal drug
A synthesis method and compound technology, applied in antifungal agents, botany equipment and methods, applications, etc., can solve the problems of exacerbating the difficulty of treating fungal infections and narrow antibacterial spectrum
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Embodiment 1
[0040] Example 1: Synthesis and preparation of 3-(1H-1,2,4-triazol-1-yl)-4-hydroxythiochroman (Formula Ia1) The reaction formula is as follows:
[0041]
[0042] Follow the steps to prepare:
[0043] Take 22.4mmol of 2-ethylthio-3-(1H-1,2,4-triazol-1-yl)thiochromone compound, dissolve it in 50mL of 50% ethanol; add 89.6mmol of sodium borohydride in batches The above solution was stirred overnight at room temperature, the solvent was distilled off under reduced pressure, the solid was extracted with 50 mL of ethyl acetate and 50 mL of water, the ethyl acetate layer was taken, washed twice with water (50 mL×2), and the organic layer was recovered and evaporated to dryness. The product of formula (Ia1) 3-(1H-1,2,4-triazol-1-yl)-4-hydroxythiochroman was 19.3 mmol, and the yield was 86%.
[0044] 1 H NMR (CDCl 3):8.77(s,1H),8.06(s,1H),7.26-7.32(m,3H),7.14(t,1H),5.17(d,1H),4.50(d,1H),4.42-4.44( m,1H),3.30-3.34(m,1H),3.06-3.08(m,1H).
Embodiment 2- Embodiment 19
[0045] Example 2-Example 19: Preparation of thiochroman compounds of formula (Ia)
[0046] The compound of formula (II) is used as the raw material to prepare the compound of formula (Ia) (the target product is each compound of formula (Ia2) to formula (Ia19) in Table 1), and the reaction formula is as follows:
[0047]
[0048] The preparation steps are as follows:
[0049] Take 22.4 mmol of the compound of formula (II) and dissolve it in a polar solvent, add 89.6 mmol of reducing agent into the solution in batches, stir overnight at room temperature, and process according to the method of Example 1 to obtain formula (Ia2) to formula (Ia19) Various sulfur chroman compounds.
[0050] In Examples 2 to 19, the selection of each group of the thiochromans of the product formula (Ia), the preparation reagents and the detection data are listed in Table 1.
[0051] Table 1
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[0054]
Embodiment 20
[0055] Example 20: Synthesis of 3-(1H-1,2,4-triazol-1-yl)-4-hydroxy-1-thiochroman oxide
[0056] Using 3-(1H-1,2,4-triazol-1-yl)-4-hydroxythiochroman as raw material, the target product (Ib1) thiochroman compounds were prepared.
[0057] The preparation reaction formula is as follows:
[0058]
[0059] The preparation steps are as follows:
[0060] Take 19.3mmol of the raw material 3-(1H-1,2,4-triazol-1-yl)-4-hydroxythiochroman, add it to 35mL acetic anhydride solvent, acetylation reaction occurs to protect the hydroxyl group, and distill under reduced pressure after the reaction Remove the acetic anhydride solvent. Add 30mL of saturated sodium bicarbonate solution and 30mL of ethyl acetate, separate the ethyl acetate layer; extract the water layer with 20mL of ethyl acetate and combine the organic layer, then add 3.4g of 30% concentration of hydrogen peroxide (20mmol ) undergoes an oxidation reaction. After the reaction, wash with 10 mL of saturated sodium sulfite solut...
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