522-17-8
522-17-8 結(jié)構(gòu)式
基本信息
魚藤素
(-)-DEGUELIN
AKT抑制劑(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
物理化學(xué)性質(zhì)
制備方法
![(6AS,12AS)-6A,12A-二氫-9-羥基-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-二氫-9-羥基-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)-酮為原料，合成(7aS,13aS)-9,10-二甲氧基-3,3-二甲基-13,13a-二氫-3H-吡喃并[2,3-c:6,5-f']二苯并吡喃-7(7aH)-酮的一般步驟如下： 1. 在氬氣保護(hù)下，將苯基硒基氯（68 mg，0.35 mmol）加入到含有(6AS,12AS)-6A,12A-二氫-9-羥基-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）的無水二氯甲烷溶液（4.0 mL）中，反應(yīng)溫度為-30℃，攪拌10分鐘。 2. 緩慢升溫至室溫，繼續(xù)攪拌2小時，隨后再攪拌1小時。 3. 減壓除去溶劑，將殘余物溶解于四氫呋喃（4.0 mL）中，在0℃下加入30%過氧化氫水溶液（0.06 mL）。 4. 攪拌反應(yīng)混合物至室溫，期間通過薄層色譜（TLC）監(jiān)測反應(yīng)進(jìn)度。 5. 反應(yīng)完成后，加入乙酸乙酯（8.0 mL）和水（4.0 mL），分離有機(jī)層。 6. 有機(jī)層依次用5%碳酸氫鈉水溶液和鹽水洗滌，經(jīng)硫酸鎂干燥，過濾后濃縮。 7. 通過快速柱色譜法（乙酸乙酯:正己烷=1:2）純化粗產(chǎn)物，得到淡黃色固體狀的(7aS,13aS)-9,10-二甲氧基-3,3-二甲基-13,13a-二氫-3H-吡喃并[2,3-c:6,5-f']二苯并吡喃-7(7aH)-酮，產(chǎn)率61%（78 mg）。 產(chǎn)物表征數(shù)據(jù)： 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) 計算值 C23H23O6 (M+H+): 395.1495, 測得: 395.1495。
參考文獻(xiàn)：
[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
| 報價日期 | 產(chǎn)品編號 | 產(chǎn)品名稱 | CAS號 | 包裝 | 價格 |
| 2025/12/22 | HY-13425 | 魚藤素 Deguelin | 522-17-8 | 5mg | 424元 |
| 2025/12/22 | HY-13425 | 魚藤素 Deguelin | 522-17-8 | 10mM * 1mLin DMSO | 542元 |
| 2025/12/22 | HY-13425 | 魚藤素 Deguelin | 522-17-8 | 10mg | 784元 |
常見問題列表
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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.