1-[5-(adamant-1-yl)-2-(but-1-oxy)-4-(2-methoxyethoxymethoxy)-phenyl]-ethan-1-one | 1175994-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[5-(adamant-1-yl)-2-(but-1-oxy)-4-(2-methoxyethoxymethoxy)-phenyl]-ethan-1-one
• CAS: 1175994-09-8
• 化学式: C₂₆H₃₈O₅
• 分子量: 430.585
• InChiKey: GFOFVSMPHKNKAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[5-(adamant-1-yl)-2-(but-1-oxy)-4-(2-methoxyethoxymethoxy)-phenyl]-ethan-1-one 、 对甲酰基苯甲酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以58%的产率得到(E)-4-[3-(5-(adamant-1-yl)-2-(but-1-oxy)-4-(2-methoxyethoxymethoxy)-phenyl)-3-oxoprop-1-en-1-yl]benzoic acid
  参考文献：
  名称：

  Inhibition of IκB Kinase-β and Anticancer Activities of Novel Chalcone Adamantyl Arotinoids

  摘要：

  On the basis of the observations that chalcone 7 (MX781) and some related adamantyl arotinoids (AdArs) inhibit I kappa B alpha kinase beta (IKK beta) activity, inhibit cell growth, and induce apoptosis in cancer cells, a new series of AdArs structurally related to 7 have been designed and synthesized. Modifications were intended to reduce or eliminate RAR activity, and we evaluated the effect of the novel analogues of 7 on IKK beta activity and proliferation of a variety of cancer cell lines (leukemia, Jurkat; prostate, PC-3; breast carcinomas, T47D, MDA-MB-468). Consistent with the design principles, the biological activities of these AdArs do not appear to be RAR-mediated, since most analogues are unable to activate RAR-mediated transactivation and exhibit significantly diminished antagonist activity. All compounds are capable of inducing apoptosis in Jurkat cells, as demonstrated by elevated DEVDase activity and externalization of phosphatidylserine. Several of the analogues elicit stronger growth inhibitory activity against prostate (PC-3) and breast (MDA-MB-468) carcinoma cells, which contain elevated basal IKK activity; this antiproliferative activity correlates with increased inhibition of recombinant IKK beta in vitro, suggesting that the anticancer activities of these AdArs might be related to the inhibition of' IKK/NF kappa B signaling.

  DOI：

  10.1021/jm800285f
• 作为产物：
  描述：

  1-碘丁烷 、 1-[5-(adamant-1-yl)-2-hydroxy-4-(2-methoxyethoxymethoxy)-phenyl]-ethan-1-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 16.5h， 以59%的产率得到1-[5-(adamant-1-yl)-2-(but-1-oxy)-4-(2-methoxyethoxymethoxy)-phenyl]-ethan-1-one
  参考文献：
  名称：

  Inhibition of IκB Kinase-β and Anticancer Activities of Novel Chalcone Adamantyl Arotinoids

  摘要：

  On the basis of the observations that chalcone 7 (MX781) and some related adamantyl arotinoids (AdArs) inhibit I kappa B alpha kinase beta (IKK beta) activity, inhibit cell growth, and induce apoptosis in cancer cells, a new series of AdArs structurally related to 7 have been designed and synthesized. Modifications were intended to reduce or eliminate RAR activity, and we evaluated the effect of the novel analogues of 7 on IKK beta activity and proliferation of a variety of cancer cell lines (leukemia, Jurkat; prostate, PC-3; breast carcinomas, T47D, MDA-MB-468). Consistent with the design principles, the biological activities of these AdArs do not appear to be RAR-mediated, since most analogues are unable to activate RAR-mediated transactivation and exhibit significantly diminished antagonist activity. All compounds are capable of inducing apoptosis in Jurkat cells, as demonstrated by elevated DEVDase activity and externalization of phosphatidylserine. Several of the analogues elicit stronger growth inhibitory activity against prostate (PC-3) and breast (MDA-MB-468) carcinoma cells, which contain elevated basal IKK activity; this antiproliferative activity correlates with increased inhibition of recombinant IKK beta in vitro, suggesting that the anticancer activities of these AdArs might be related to the inhibition of' IKK/NF kappa B signaling.

  DOI：

  10.1021/jm800285f