3,9-dibenzylcarbonyl-1,5,7,11-tetrahydroxymethyl-6,12-bis(4-methoxyphenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,9-dibenzylcarbonyl-1,5,7,11-tetrahydroxymethyl-6,12-bis(4-methoxyphenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane
• 英文别名: 3,9-Dibenzylcarbonyl-1,5,7,11-tetrahydroxymethyl-6,12-bis(4-methoxyphenyl)-3,9-diazahexacyclo[6.4.0.02.7.04.11.05.10]dodecane；2-phenyl-1-[1,5,7,11-tetrakis(hydroxymethyl)-6,12-bis(4-methoxyphenyl)-9-(2-phenylacetyl)-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecan-3-yl]ethanone
• 化学式: C₄₄H₄₆N₂O₈
• 分子量: 730.858
• InChiKey: BWGFJSDAEQLDOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  tetramethyl 3,9-dibenzylcarbonyl-6,12-bis(4-methoxyphenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate 在 calcium borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 672000.0h， 以90%的产率得到3,9-dibenzylcarbonyl-1,5,7,11-tetrahydroxymethyl-6,12-bis(4-methoxyphenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane
  参考文献：
  名称：

  Cage DimericN-Acyl- andN-Acyloxy-4-aryl-1,4-dihydropyridines as First Representatives of a Novel Class of HIV-1 Protease Inhibitors

  摘要：

  The synthesis of a series of novel cage dimeric N-acyl and N-acyl-oxy-3-aryl-1,4-dihydropyridines starting either from solid-state synthetic ester dimers or hom monomeric 4-aryl-1,4-dihydropyridines is presented. Their biological evaluation as novel HIV-1 protease inhibitors showed the most active compounds to be 5c and 5i with inhibitory activities of 52% (50 mu M) and 49% (25 mu M), respectively. Within each series of N-acyl- and N-acyloxy derivatives NCOBz and NBoc groups were found to be the best substituents. Although they exhibiting only moderate activities these cage dimers hold promise as a class of novel non-peptidic HIV-1 protease inhibitors.

  DOI：

  10.1002/(sici)1521-4184(199911)332:11<380::aid-ardp380>3.0.co;2-t

文献信息

• Cage DimericN-Acyl- andN-Acyloxy-4-aryl-1,4-dihydropyridines as First Representatives of a Novel Class of HIV-1 Protease Inhibitors
  作者：Andreas Hilgeroth、Andreas Billich

  DOI：10.1002/(sici)1521-4184(199911)332:11<380::aid-ardp380>3.0.co;2-t

  日期：1999.11

  The synthesis of a series of novel cage dimeric N-acyl and N-acyl-oxy-3-aryl-1,4-dihydropyridines starting either from solid-state synthetic ester dimers or hom monomeric 4-aryl-1,4-dihydropyridines is presented. Their biological evaluation as novel HIV-1 protease inhibitors showed the most active compounds to be 5c and 5i with inhibitory activities of 52% (50 mu M) and 49% (25 mu M), respectively. Within each series of N-acyl- and N-acyloxy derivatives NCOBz and NBoc groups were found to be the best substituents. Although they exhibiting only moderate activities these cage dimers hold promise as a class of novel non-peptidic HIV-1 protease inhibitors.