Anti-tumor stem cell shikonin and alkannin oxime derivative
A technology of derivatives and stem cells, applied in the field of medicine, can solve problems such as limiting clinical application, and achieve the effects of easy availability of raw materials, clear structure and high yield
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Embodiment 1
[0032]
[0033] This embodiment relates to (S)-2-(1-isoamyloxy-4-methyl-3-pentenyl)-1,4,5,8-tetramethyl having structural formula (II-1) The preparation method of oxynaphthalene, such as figure 1 shown, including the following steps:
[0034] Using literature (Liming Zhao et al, Letters in Organic Chemistry, 2008, 5, 234-236; Xu Yan et al, Asymmetric total synthesis of shikonin and akanin. Journal of Shenyang Pharmaceutical University, 2014, 3 1(6), 440-443,482) reported method, using 1,4,5,8-tetramethoxy-2-naphthalene carboxaldehyde as raw material to prepare (S)-2-(1-hydroxy-4-methyl-3-pentene) base)-1,4,5,8-tetramethoxynaphthalene (X-S). Take (S)-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4,5,8-tetramethoxynaphthalene (X-S, 1.7g, 5.0mmol) to dissolve Anhydrous DMF (30.0 mL) was added with 60% NaH (1.0 g, 25.0 mmol) under ice bath and nitrogen protection. After 30 min, iodoisopentane (5.0 g, 25.0 mmol) was slowly added dropwise to the reaction solution After 20 min, the temp...
Embodiment 2
[0036]
[0037] This embodiment relates to (S)-6-(1'-isoamyloxy-4'-methyl-3'-pentenyl)-5,8-dimethoxy having structural formula (II-2) The preparation method of base-1,4-naphthalenedione dioxime, such as figure 1 shown, including the following steps:
[0038] (S)-2-(1-isopentyloxy-4-methyl-3-pentenyl)-1,4,5,8-tetramethoxynaphthalene (II-1, 1.25 g, 3.0 mmol ) was dissolved in dichloromethane-acetonitrile mixed solvent (3:1, V / V, 45 mL), an aqueous solution (4.5 mL) of ceric ammonium nitrate (4.24 g, 7.7 mmol) was added under an ice bath, and after the reaction was completed, dichloro Methane extraction, the organic layer was washed with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, the crude product was subjected to silica gel column chromatography to obtain a yellow oil (0.31 g). The yellow color was dissolved in absolute ethanol (24.0 mL) and pyridine (5.50 mL), and hydroxylamine hydrochloride (0.39 g, 5.6 mmol) was added under nitrogen prot...
Embodiment 3
[0040]
[0041] The present embodiment relates to (R)-6-(1'-isoamyloxy-4'-methyl-3'-pentenyl)-5,8-dimethoxy having structural formula (II-2) The preparation method of base-1,4-naphthalenedione dioxime, such as figure 1 shown, including the following steps:
[0042] Using literature (Liming Zhao et al, Letters in Organic Chemistry, 2008, 5, 234-236; Xu Yan et al, Asymmetric total synthesis of shikonin and akanin. Journal of Shenyang Pharmaceutical University, 2014, 31(6), 440 -443,482) reported method, using 1,4,5,8-tetramethoxy-2-naphthalene carboxaldehyde as raw material to prepare (R)-2-(1-hydroxy-4-methyl-3-pentenyl )-1,4,5,8-tetramethoxynaphthalene (X-R). Then use (R)-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4,5,8-tetramethoxynaphthalene (X-R) as raw material, adopt and Example 1 and Example 2 were the same experimental procedures to prepare compound II-3. The compound was pale yellow powder with a yield of 63.6%. 1 H NMR (400 MHz, DMSO-d 6 )δ12.02(s,2H),7.42–7.28(m,2H...
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