(2S,3R,4S,4aR)-2,3,4-triethoxy-5-ethyl-2,3,4,4a-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one | 1431555-87-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: (2S,3R,4S,4aR)-2,3,4-triethoxy-5-ethyl-2,3,4,4a-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• CAS: 1431555-87-1
• 化学式: C₂₂H₂₉NO₆
• 分子量: 403.475
• InChiKey: RUJDKXQNTIMGJB-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  溴乙烷 、 2alpha,3beta,4beta-三羟基-2,3,4,4abeta,5,6-六氢[1,3]二氧杂环戊并[4,5-j]菲啶-6-酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (2S,3R,4S,4aR)-2,3,4-triethoxy-5-ethyl-2,3,4,4a-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one
  参考文献：
  名称：

  Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70)

  摘要：

  The anti hepatitis C virus (HCV) activity of (+)-lycoricidine (1) was evaluated for the first time in this letter, yielding an EC50 value of 0.55 nmol/mL and an selection index (SI) value of 12.72. Further studies indicated that 1 induced this effect by down-regulating host heat-stress cognate 70 (Hsc70) expression. In addition, 20 derivatives were designed and synthesised to investigate the basic structure-activity relationship (SAR) of the title compound. Several of these derivatives exhibit a good inhibition of HCV, such as compound 3 (EC50 = 0.68 nmol/mL, SI = 33.86), compound 2d (EC50 = 15 nmol/mL, SI = 12) and compound 5 (EC50 = 33 nmol/mL, SI > 10.91). Meanwhile, the experimental data suggest that the modification of certain groups of (+)-lycoricidine can reduce the cytotoxicity of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.089