tetramethyl-6,12-diphenyl-3,9-diazahexacyclo<6.4.0.0(2,7).0(4,11).0(5,10)>dodecane-1,5,7,11-tetracarboxylate | 210427-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tetramethyl-6,12-diphenyl-3,9-diazahexacyclo<6.4.0.0(2,7).0(4,11).0(5,10)>dodecane-1,5,7,11-tetracarboxylate
• 英文别名: Tetramethyl 6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate
• CAS: 210427-45-5
• 化学式: C₃₀H₃₀N₂O₈
• 分子量: 546.577
• InChiKey: IFSUDENSECYDTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tetramethyl-6,12-diphenyl-3,9-diazahexacyclo<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 672002.0h， 生成 1,5,7,11-tetrahydroxymethyl-3,9-dimethoxycarbonyl-6,12-diphenyl-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
• 作为产物：
  描述：

  以97%的产率得到tetramethyl-6,12-diphenyl-3,9-diazahexacyclo<6.4.0.0(2,7).0(4,11).0(5,10)>dodecane-1,5,7,11-tetracarboxylate
  参考文献：
  名称：

  二聚体4-芳基-1,4-二氢吡啶的新型固态合成

  摘要：

  在固态辐射下，4-芳基-1,4-二氢吡啶1经历[2 + 2]环二酮至中心对称的头对尾二聚体3和4a。该笼二聚体几乎只形成3 经由与c 2 -对称顺-dimers 2发生在几乎定量的产率，在与所述的环加成反应对比度抗-dimer 4a中，这是伴随着光氧化，以吡啶5a中。

  DOI：

  10.1002/jhet.5570350217

文献信息

• Novel solid-state synthesis of dimeric 4-aryl-1,4-dihydropyridines
  作者：Andreas Hilgeroth、Frank W. Heinemann

  DOI：10.1002/jhet.5570350217

  日期：1998.3

  On irradiation in the solid state the 4-aryl-1,4-dihydroypridines 1 undergo [2+2] cycloadditon to centrosymmetric head-to-tail dimers 3 and 4a. The almost exclusive formation of the cage dimers 3 via the C2-symmetric syn-dimers 2 takes place in nearly quantitative yields, in contrast with the cycloaddition reaction of the anti-dimer 4a, which is accompanied by photooxidation to pyridine 5a.

  在固态辐射下，4-芳基-1,4-二氢吡啶1经历[2 + 2]环二酮至中心对称的头对尾二聚体3和4a。该笼二聚体几乎只形成3 经由与c 2 -对称顺-dimers 2发生在几乎定量的产率，在与所述的环加成反应对比度抗-dimer 4a中，这是伴随着光氧化，以吡啶5a中。
• 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.