3,9-dibenzyl-1,5,7,11-tetrahydroxymethyl-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate | 252671-48-0

• 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-dibenzyl-1,5,7,11-tetrahydroxymethyl-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate
• 英文别名: 3,9-dibenzyl-1,5,7,11-tetrahydroxymethyl-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
• CAS: 252671-48-0
• 化学式: C₄₀H₄₂N₂O₄
• 分子量: 614.784
• InChiKey: MHLQADKLDLZTOZ-KPJQDINUSA-N

物化性质

• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  87.4
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,9-dibenzyl-1,5,7,11-tetrahydroxymethyl-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate 、 乙酰氯 在 吡啶 作用下， 反应 72.0h， 以50%的产率得到3,9-dibenzyl-6,12-diphenyl-3,9-diazahexacyclo[6.4.0.0(2,7).0(4,11).0(5,10)]dodecane-1,5,7,11-tetrakis(methyleneacetate)
  参考文献：
  名称：

  Evaluation of substrate and inhibitor properties of a novel MDR modulator H17 towards transmembrane efflux pumps

  摘要：

  Substrate and inhibitor properties of H17 as novel modulator of transmembrane efflux pump activities have been characterized in an in situ absorption model. Poor substrate properties towards P glycoprotein (P-gp) and multidrug resistance-associated protein (MRP) have been demonstrated. In competition with a MRP substrate H17 proved to have strong MRP-inhibiting properties. The profile of a strong inhibitor with poor substrate properties makes H17 a perspective hopeful candidate for effective therapies of transmembrane efflux pump activities. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.07.014
• 作为产物：
  描述：

  DIETHYL1-BENZYL-4-PHENYL-1,4-DIHYDROPYRIDINE-3,5-DICARBOXYLATE锛圵S201542锛,WUXIAPPTEC" 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3,9-dibenzyl-1,5,7,11-tetrahydroxymethyl-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]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