522-17-8
基本信息
魚藤素
(-)-DEGUELIN
AKT抑制剂(DEGUELIN)
Ccris 8104
()-Deguelin
(-)-DEGUELIN
(7as-cis)-oxy-
Deguelin (6CI)
(-)-cis-Deguelin
12a-DEOXYTEPHROSIN
(-)-DEGUELIN
(-)-CIS-DEGUELIN
3h-bis(1)benzopyrano(3,4-b:6’,5’-e)pyran-7(7ah)-one,13,13a-dihydro-9,10-dimeth
物理化学性质
| 熔点 | 85-87 °C(lit.) |
| 比旋光度 | D27 -97.2° (c = 0.2 in benzene) |
| 沸点 | 560.1±50.0 °C(Predicted) |
| 密度 | 1?+-.0.06 g/cm3(Predicted) |
| 储存条件 | -20°C |
| 溶解度 | DMSO: >10 mg/mL |
| 形态 | solid |
| 颜色 | white to yellow |
| 旋光度 (Optical Rotation) | [α]/D -70 to -80°, c = 0.2 in methanol |
| 稳定性 | 从购买之日起 2 年内保持稳定。 DMSO 或乙醇溶液可在 -20℃ 下保存长达 3 个月。 |
制备方法
![(6AS,12AS)-6A,12A-二氢-9-羟基-2,3-二甲氧基-8-(3-甲基-2-丁烯-1-基)[1]苯并吡喃并[3,4-B][1]苯并吡哆醇-12(6H)-酮](/CAS/20210305/GIF/70191-71-8.gif)
70191-71-8
522-17-8
以(6AS,12AS)-6A,12A-二氢-9-羟基-2,3-二甲氧基-8-(3-甲基-2-丁烯-1-基)[1]苯并吡喃并[3,4-B][1]苯并吡哆醇-12(6H)-酮为原料，合成(7aS,13aS)-9,10-二甲氧基-3,3-二甲基-13,13a-二氢-3H-吡喃并[2,3-c:6,5-f']二苯并吡喃-7(7aH)-酮的一般步骤如下： 1. 在氩气保护下，将苯基硒基氯（68 mg，0.35 mmol）加入到含有(6AS,12AS)-6A,12A-二氢-9-羟基-2,3-二甲氧基-8-(3-甲基-2-丁烯-1-基)[1]苯并吡喃并[3,4-B][1]苯并吡哆醇-12(6H)-酮（128 mg，0.32 mmol）的无水二氯甲烷溶液（4.0 mL）中，反应温度为-30℃，搅拌10分钟。 2. 缓慢升温至室温，继续搅拌2小时，随后再搅拌1小时。 3. 减压除去溶剂，将残余物溶解于四氢呋喃（4.0 mL）中，在0℃下加入30%过氧化氢水溶液（0.06 mL）。 4. 搅拌反应混合物至室温，期间通过薄层色谱（TLC）监测反应进度。 5. 反应完成后，加入乙酸乙酯（8.0 mL）和水（4.0 mL），分离有机层。 6. 有机层依次用5%碳酸氢钠水溶液和盐水洗涤，经硫酸镁干燥，过滤后浓缩。 7. 通过快速柱色谱法（乙酸乙酯:正己烷=1:2）纯化粗产物，得到淡黄色固体状的(7aS,13aS)-9,10-二甲氧基-3,3-二甲基-13,13a-二氢-3H-吡喃并[2,3-c:6,5-f']二苯并吡喃-7(7aH)-酮，产率61%（78 mg）。 产物表征数据： 1H-NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J = 8.7 Hz), 6.77 (s, 1H), 6.62 (d, 1H, J = 10.0 Hz), 6.43 (s, 1H), 6.43 (d, 1H, J = 8.7 Hz), 5.53 (d, 1H, J = 10.0 Hz), 4.89 (m, 1H), 4.61 (dd, 1H, J = 12.0, 3.1 Hz), 4.17 (d, 1H, J = 12.0 Hz), 3.82 (d, 1H, J = 4.1 Hz), 3.78 (s, 3H), 3.75 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3H); 13C-NMR (CDCl3, 100 MHz) δ 189.2, 160.0, 156.9, 149.4, 147.4, 143.8, 128.6, 128.5, 115.7, 112.7, 111.4, 110.4, 109.1, 104.7, 100.9, 77.6, 72.4, 66.2, 56.3, 55.8, 44.3, 28.4, 28.1; HRMS (FAB) 计算值 C23H23O6 (M+H+): 395.1495, 测得: 395.1495。
参考文献：
[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 24, p. 10863 - 10884
[2] Patent: EP2871187, 2015, A1. Location in patent: Paragraph 0482-0486
[3] Patent: US2015/183797, 2015, A1. Location in patent: Paragraph 0582-0586
[4] Journal of the Chemical Society, Chemical Communications, 1986, # 4, p. 352 - 353
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1685 - 1698
Deguelin价格(试剂级)
| 报价日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
| 2025/05/22 | HY-13425 | 魚藤素 Deguelin | 522-17-8 | 5mg | 424元 |
| 2025/05/22 | HY-13425 | 魚藤素 Deguelin | 522-17-8 | 10mM * 1mLin DMSO | 542元 |
| 2025/05/22 | HY-13425 | 魚藤素 Deguelin | 522-17-8 | 10mg | 784元 |
常见问题列表
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Akt
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Deguelin (0-500 nM) in a dose and time dependent manner inhibits the growth of MDA-MB-231, MDA-MB-468, BT-549 and BT-20 cells. Deguelin at all concentrations fails to reduce cell numbers in the presence of 1 ng EGF but in the presence of EGF 20 ng reinstated deguelin mediated growth inhibition. Deguelin treated cells show reduced expression of Survivin as determined by western blot and immunofluorescence examinations. Deguelin inhibits p-ERK and its downstream target p-STAT-3 and c-Myc expression in a dose dependent manner. Deguelin down-regulates Akt signaling probably by disrupting its association with Hsp 90 in cultured HNSCC cells. Deguelin deguelin disrupts the association between Hsp 90 with survivin and Cdk4. Deguelin deguelin treatment increases cellular ceramide level through de novo synthase pathway to mediate HNSCC cell death and apoptosis. Deguelin inhibits the proliferation of MPC-11 cells in a concentration- and time-dependent manner and causes the apoptotic death of MPC-11 cells. Following exposure to deguelin, the phosphorylation of Akt is decreased. Deguelin-induced apoptosis is characterized by the upregulation of Bax, downregulation of Bcl-2 and activation of caspase-3.
Deguelin (2 or 4 mg/kg, i.p.) reduces the in vivo tumor growth of MDA-MB-231 cells transplanted subcutaneously in athymic mice. Deguelin (4 mg/kg, p.o.) treatment shows a great inhibition in tumor growth, which is demonstrated by reduced tumor size and improved mice survival and, indicating a significant anti-tumor ability by deguelin in vivo. In the colon cancer xenograft model, the volume of the tumor treated with deguelin is significantly lower than that of the control, and the apoptotic index for deguelin-treated mice is much higher.