[(9R,10R)-2-cyano-3,8,8-trimethyl-4-oxo-9-[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]oxy-9,10-dihydropyrano[2,3-f]chromen-10-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate | 1253849-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [(9R,10R)-2-cyano-3,8,8-trimethyl-4-oxo-9-[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]oxy-9,10-dihydropyrano[2,3-f]chromen-10-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 1253849-51-2
• 化学式: C₃₆H₃₉NO₁₁
• 分子量: 661.706
• InChiKey: HQJIPHHCJPOOEF-CTAQNPQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  48
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  sodium cyanide 、 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以22%的产率得到[(9R,10R)-2-cyano-3,8,8-trimethyl-4-oxo-9-[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]oxy-9,10-dihydropyrano[2,3-f]chromen-10-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Anti-AIDS agents 79. Design, synthesis, molecular modeling and structure–activity relationships of novel dicamphanoyl-2′,2′-dimethyldihydropyranochromone (DCP) analogs as potent anti-HIV agents

  摘要：

  In a continued study, 23 3'R,4'R-di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) derivatives (5-27) were synthesized, and screened for anti-HIV activity against both a non-drug-resistant NL4-3 strain and multiple reverse transcriptase (RT) inhibitor-resistant (RTMDR-1) strain, using 2-EDCP (4) and 2-MDCP (35) as controls. New DCP analogs 5, 9, 14, and 22 exhibited potent anti-HIV activity against HIV(NL4-3) with EC(50) and therapeutic index (TI) values ranging from 0.036 mu M to 0.14 mu M and from 110 to 420, respectively. Compounds 5 and 9 also exhibited good activity against RTMDR-1 (EC(50) 0.049 and 0.054 mu M; TI 310 and 200, respectively), and were twofold more potent than the leads 4 and 35 (EC(50) 0.11 and 0.19 mu M; TI 60 and 58, respectively). Evaluation of water solubility showed that 5 and 22 were 5-10 times more water soluble than 4. Quantitative structure-activity relationship (QSAR) modeling results were first performed on this compound type, and the models should aid in design of future anti-HIV DCP analogs and potential clinical drug candidates. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.065