A kind of nitroimidazole compound and its application in pharmacy
A compound, nitro technology, applied in the fields of pharmacology, medicinal chemistry and pharmacology, can solve the problems of low oral bioavailability, serious adverse reactions, poor effect, etc., to improve the activity of anti-mycobacterium tuberculosis, strong anti- Mycobacterium tuberculosis effect, effect of excellent pharmacokinetic properties
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preparation example 1
[0093] Preparation 1 5-(4-(trifluoromethoxy)phenoxy)isoindole (TH-1)
[0094]
[0095] tert-butyl 5-hydroxyisoindole-2-carboxylate (470 mg, 2.0 mmol, synthesized by reference Bioorg.Med.Chem.Lett., 2001, 11(5), 685-688) and 1-bromo 4-tri Fluoromethoxybenzene (481mg, 2.0mmol) was dissolved in 1,4-dioxane (10mL), copper iodide (38mg, 0.2mmol), N,N-dimethylglycine (62mg, 0.6 mmol), cesium carbonate (977mg, 3.0mmol), heated to reflux for 24h under the protection of argon, the reaction was completed, filtered, concentrated, column chromatography (CH 2 Cl 2 / CH 3 OH=100 / 1), the resulting product is directly put into the next step reaction.
[0096] The intermediate obtained in the previous step was dissolved in dichloromethane (10 mL), and the mixture was cooled with ice salt, and trifluoroacetic acid (10 mL) was added. After the addition was complete, the mixture was reacted at room temperature for 3 hours, stopped the reaction, and concentrated. The residue was dissolved in d...
preparation example 2
[0098] Preparation 2 5-(4-(trifluoromethyl)phenoxy)isoindole (TH-2)
[0099]
[0100] Using tert-butyl 5-hydroxyisoindole-2-carboxylate (470 mg, 2.0 mmol) and 1-bromo-4-trifluoromethylbenzene (450 mg, 2.0 mmol) as starting materials, the intermediate product was obtained similarly to the synthesis of TH-1 TH-2 (340 mg, 61%).
[0101] MS(ESI / LR):280.1[M+1] + .
preparation example 3
[0102] Preparation 3 7-(4-(trifluoromethoxy)phenoxy)-1,2,3,4-tetrahydroisoquinoline (TH-3)
[0103]
[0104] With tert-butyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (498mg, 2.0mmol, reference Bioorg.Med.Chem.,2009,17(23),7850-7860 Synthesis) and 1-bromo-4-trifluoromethoxybenzene (481mg, 2.0mmol) as raw materials, similar to the synthesis of TH-1, the intermediate product TH-3 (402mg, 65%) was obtained.
[0105] MS(ESI / LR):310.1[M+1] + .
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