(2S,2S')-N,N'-(methylenedi-4,1-phenylene)bis(1-tert-butoxycarbonyl-2-pyrrolidinecarboxamide) | 1310561-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,2S')-N,N'-(methylenedi-4,1-phenylene)bis(1-tert-butoxycarbonyl-2-pyrrolidinecarboxamide)
• 英文别名: tert-butyl (2S)-2-[[4-[[4-[[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carbonyl]amino]phenyl]methyl]phenyl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 1310561-43-3
• 化学式: C₃₃H₄₄N₄O₆
• 分子量: 592.736
• InChiKey: QSZJDSONJYELPO-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,2S')-N,N'-(methylenedi-4,1-phenylene)bis(1-tert-butoxycarbonyl-2-pyrrolidinecarboxamide) 在 盐酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以99%的产率得到(2S,2S')-N,N'-(methylenedi-4,1-phenylene)bis(2-pyrrolidinecarboxamide)
  参考文献：
  名称：

  Synthesis of GN8 derivatives and evaluation of their antiprion activity in TSE-infected cells

  摘要：

  A series of GN8 derivatives were synthesized from various diamines, carboxylic acid derivatives, and nitrogen nucleophiles, and their antiprion activity was tested in TSE-infected mouse neuronal cells. We found that two ethylenediamine units, hydrophobic substituents on the nitrogen atoms, and the diphenylmethane scaffold were essential structural features responsible for the activity. Seven derivatives bearing substituents at the benzylic position exhibited an improved antiprion activity with the IC50 values of 0.51-0.83 mu M. Conformational analysis of model compounds suggested that the introduction of the substituent at the benzylic position restricted the conformational variability of the diphenylmethane unit. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.132
• 作为产物：
  描述：

  4,4'-二硝基二苯基甲烷 在 tin(II) chloride dihdyrate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (2S,2S')-N,N'-(methylenedi-4,1-phenylene)bis(1-tert-butoxycarbonyl-2-pyrrolidinecarboxamide)
  参考文献：
  名称：

  HCV NS5A replication complex inhibitors. Part 3: discovery of potent analogs with distinct core topologies

  摘要：

  In a recent disclosure,(1) we described the discovery of dimeric, prolinamide-based NS5A replication complex inhibitors exhibiting excellent potency towards an HCV genotype 1b replicon. That disclosure dealt with the SAR exploration of the peripheral region of our lead chemotype, and herein is described the SAR uncovered from a complementary effort that focused on the central core region. From this effort, the contribution of the core region to the overall topology of the pharmacophore, primarily vector orientation and planarity, was determined, with a set of analogs exhibiting < 10 nM EC50 in a genotype 1b replicon assay. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.086