tetraethyl 6,12-di(3,4,5-trimethoxylphenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate | 1580417-08-8

• 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: tetraethyl 6,12-di(3,4,5-trimethoxylphenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
• CAS: 1580417-08-8
• 化学式: C₄₀H₅₀N₂O₁₄
• 分子量: 782.842
• InChiKey: HUDIADLJGVMBCG-ZLVXFCMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  184.64
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  diethyl 4-(3,4,5-trimethoxylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate 以 四氢呋喃 、 甲醇 为溶剂， 以55.3%的产率得到tetraethyl 6,12-di(3,4,5-trimethoxylphenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of 3,9-diazatetraasteranes as Novel Matrilysin Inhibitors

  摘要：

  Matrilysin is an ideal biological target to develop novel inhibitors because it is overexpressed in malignant tumour cells. A series of 3,9‐diazatetraasteranes was designed as inhibitors of matrilysin, which was an ideal biological target because it is responsible for aggressive malignant phenotypes and poor prognoses implicated in many cancers. Docking simulation supported the initial pharmacophore hypothesis and suggested a common interaction mechanism of 3,9‐diazatetraasteranes with the catalytic site of matrilysin. The 3,9‐diazatetraasteranes were synthesized by the photocyclization of 4‐aryl‐1,4‐dihydropyridines, and their structures were determined using 1H NMR, 13C NMR and MS. The inhibitory activities of these compounds on matrilysin were investigated in vitro using an MTT assay in A549 (small cell lung cancer) cells. The results show that the 3,9‐diazatetraasteranes can inhibit the growth of A549 tumour cells. The best IC50 value is approximately 50 μm. This result indicates that 3,9‐diazatetraasteranes will be useful pharmacological tools for the investigation of matrilysin inhibitors.

  DOI：

  10.1111/cbdd.12185

文献信息

• Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: a combined experimental and DFT study
  作者：Qiangwen Fan、Hongbo Tan、Peng Li、Hong Yan

  DOI：10.1039/c8nj02192a

  日期：——

  In this article, the hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines (1,4-DHPs) in solution was reported, wherein head-to-tail (HT) dimeric products (syn-dimers and cage dimers) were formed exclusively through successive inter- and intra-molecular [2+2] cycloaddition. The effects of irradiation wavelength, solvents and substituents on the efficiency of these transformations were

  在本文中，在异质的分子间[2 + 2]的溶液中1,4-二氢吡啶（1,4-DHP类）光环被报道，其特征在于，头-尾（HT）的二聚产物（顺式-dimers和笼二聚体）仅通过连续的分子间和分子内[2 + 2]环加成反应形成。研究了辐照波长，溶剂和取代基对这些转化效率的影响。为了阐明光环加成反应的内在特征和立体选择性，进行了DFT和TDDFT理论计算，以揭示详细的反应过程。