(S)-1-benzyl-1-morpholino-3-(1-oxo-3-phenylpropan-2-yl)urea | 1450733-55-7

• 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: (S)-1-benzyl-1-morpholino-3-(1-oxo-3-phenylpropan-2-yl)urea
• 英文别名: 1-benzyl-1-morpholin-4-yl-3-[(2S)-1-oxo-3-phenylpropan-2-yl]urea
• CAS: 1450733-55-7
• 化学式: C₂₁H₂₅N₃O₃
• 分子量: 367.448
• InChiKey: WULITDJTQGZBRF-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-phenylalaninal dimethyl acetal 在 三甲基氯硅烷 、 sodium iodide 、 碘甲烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 38.0h， 生成 (S)-1-benzyl-1-morpholino-3-(1-oxo-3-phenylpropan-2-yl)urea
  参考文献：
  名称：

  Modular construction of quaternary hemiaminal-based inhibitor candidates and their in cellulo assessment with HIV-1 protease

  摘要：

  Non-peptidomimetic drug-like protease inhibitors have potential for circumventing drug resistance. We developed a much-improved synthetic route to our previously reported inhibitor candidate displaying an unusual quaternized hemi-aminal. This functional group forms from a linear precursor upon passage into physiological media. Seven variants were prepared and tested in cellulo with our HIV-1 fusion-protein technology that result in an eGFP-based fluorescent readout. Three candidates showed inhibition potency above 20 mu M and toxicity at higher concentrations, making them attractive targets for further refinement. Importantly, our class of original inhibitor candidates is not recognized by two major multidrug resistance pumps, quite in contrast to most clinically applied HIV-1 protease inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.018

文献信息

• Modular construction of quaternary hemiaminal-based inhibitor candidates and their in cellulo assessment with HIV-1 protease
  作者：Guillaume Gros、Lorena Martinez、Anna Servat Gimenez、Paula Adler、Philippe Maurin、Roland Wolkowicz、Pierre Falson、Jens Hasserodt

  DOI：10.1016/j.bmc.2013.06.018

  日期：2013.9

  Non-peptidomimetic drug-like protease inhibitors have potential for circumventing drug resistance. We developed a much-improved synthetic route to our previously reported inhibitor candidate displaying an unusual quaternized hemi-aminal. This functional group forms from a linear precursor upon passage into physiological media. Seven variants were prepared and tested in cellulo with our HIV-1 fusion-protein technology that result in an eGFP-based fluorescent readout. Three candidates showed inhibition potency above 20 mu M and toxicity at higher concentrations, making them attractive targets for further refinement. Importantly, our class of original inhibitor candidates is not recognized by two major multidrug resistance pumps, quite in contrast to most clinically applied HIV-1 protease inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.