[(3R,4R,14R,19S)-4-[[(3aR,4S,7S,7aR)-7-(dimethylamino)-2,2,6,6-tetramethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-19-acetamido-22,25-dichloro-23-hydroxy-17-oxo-2,16-dioxapentacyclo[18.2.2.19,13.03,10.04,8]pentacosa-1(23),5,7,9,11,13(25),20(24),21-octaen-14-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1228797-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: [(3R,4R,14R,19S)-4-[[(3aR,4S,7S,7aR)-7-(dimethylamino)-2,2,6,6-tetramethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-19-acetamido-22,25-dichloro-23-hydroxy-17-oxo-2,16-dioxapentacyclo[18.2.2.19,13.03,10.04,8]pentacosa-1(23),5,7,9,11,13(25),20(24),21-octaen-14-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1228797-13-4
• 化学式: C₄₇H₄₉Cl₂F₃N₂O₁₂
• 分子量: 961.813
• InChiKey: ZCSZRYJLWUZLOC-ZKMPORMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  66
• 可旋转键数：
  9
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  N-[(3R,4R,14R,19S)-4-[[(3aR,4S,7S,7aR)-7-(dimethylamino)-2,2,6,6-tetramethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-22,25-dichloro-14,23-dihydroxy-17-oxo-2,16-dioxapentacyclo[18.2.2.19,13.03,10.04,8]pentacosa-1(23),5,7,9,11,13(25),20(24),21-octaen-19-yl]acetamide 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 11.25h， 生成 [(3R,4R,14R,19S)-4-[[(3aR,4S,7S,7aR)-7-(dimethylamino)-2,2,6,6-tetramethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-19-acetamido-22,25-dichloro-23-hydroxy-17-oxo-2,16-dioxapentacyclo[18.2.2.19,13.03,10.04,8]pentacosa-1(23),5,7,9,11,13(25),20(24),21-octaen-14-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Fijiolides A and B, Inhibitors of TNF-α-Induced NFκB Activation, from a Marine-Derived Sediment Bacterium of the Genus Nocardiopsis

  摘要：

  Fijiolide A, a potent inhibitor of TNF-alpha-induced NF kappa B activation, along with fijiolide B. were isolated from a marine-derived bacterium of the genus Nocardiopsis. The planar structures of fijiolides A (1) and B (2) were elucidated by interpretation of 2D NMR spectroscopic data, while the absolute configurations of these compounds were defined by interpretation of circular dichroism and 2D NMR data combined with application of the advanced Mosher's method. Fijiolides A and B are related to several recently isolated chloroaromatic compounds, which appear to be the Bergman cyclization products of enediyne precursors. Fijiolide A reduced TNF-alpha-induced NE kappa B activation by 70.3%, with an IC50 value of 0.57 mu M. Fijiolide B demonstrated less inhibition, only 46.5%, without dose dependence. The same pattern was also observed with quinone reductase (QR) activity: fijiolide A was found to induce quinone reductase-1 (QR1) with an induction ratio of 3.5 at a concentration of 20 mu g/mL (28.4 mu M). The concentration required to double the activity was 1.8 mu M. Fijiolide B did not affect QR1 activity, indicating the importance of the nitrogen substitution pattern for biological activity. On the basis of these data, fijiolide A is viewed as a promising lead for more advanced anticancer testing.

  DOI：

  10.1021/np100087c