N-[(2S,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-2-[(3R)-3-hydroxy methyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetamide | 1234549-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: N-[(2S,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-2-[(3R)-3-hydroxy methyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetamide
• 英文别名: N-[(2S,3S)-2-tert-butylsulfanyl-5-oxooxolan-3-yl]-2-[(3R)-3-(hydroxymethyl)-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl]acetamide
• CAS: 1234549-29-1
• 化学式: C₂₆H₂₉N₃O₅S
• 分子量: 495.599
• InChiKey: QSSIAXTWPJVJHJ-CEYNDMKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(2S,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-2-[(3R)-3-hydroxy methyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetamide 、 4-氯-2-三氟甲基异氰酸酯 以 二氯甲烷 为溶剂， 反应 12.0h， 以67%的产率得到(4-chloro-2-trifluoromethyl-phenyl)-carbamic acid 1-{[(2S,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-ylcarbamoyl]-methyl}-(3R)-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylmethyl ester (2b)
  参考文献：
  名称：

  Synthesis of novel peptidomimetics as inhibitors of protozoan cysteine proteases falcipain-2 and rhodesain

  摘要：

  This paper describes the synthesis of novel peptidomimetics bearing a protected aspartyl aldeyde warhead leading to the thioacylals 2a,b and the acylals 3a,b. Compounds 2a and 3a proved to possess an increased antiplasmodial activity with respect to the parent molecule 1. Furthermore thioacylal 2a can be considered as a promising trypanocidal agent. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.003
• 作为产物：
  描述：

  2-[(3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-N-[(2S,3S)-2-tertbutylthio-5-oxo-tetrahydrofuran-3-yl]-acetamide 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.0h， 以80%的产率得到N-[(2S,3S)-2-tert-butylthio-5-oxo-tetrahydrofuran-3-yl]-2-[(3R)-3-hydroxy methyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetamide
  参考文献：
  名称：

  Synthesis of novel peptidomimetics as inhibitors of protozoan cysteine proteases falcipain-2 and rhodesain

  摘要：

  This paper describes the synthesis of novel peptidomimetics bearing a protected aspartyl aldeyde warhead leading to the thioacylals 2a,b and the acylals 3a,b. Compounds 2a and 3a proved to possess an increased antiplasmodial activity with respect to the parent molecule 1. Furthermore thioacylal 2a can be considered as a promising trypanocidal agent. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.003

文献信息

• Synthesis of novel peptidomimetics as inhibitors of protozoan cysteine proteases falcipain-2 and rhodesain
  作者：Roberta Ettari、Maria Zappalà、Nicola Micale、Tanja Schirmeister、Christoph Gelhaus、Matthias Leippe、Astrid Evers、Silvana Grasso

  DOI：10.1016/j.ejmech.2010.04.003

  日期：2010.7

  This paper describes the synthesis of novel peptidomimetics bearing a protected aspartyl aldeyde warhead leading to the thioacylals 2a,b and the acylals 3a,b. Compounds 2a and 3a proved to possess an increased antiplasmodial activity with respect to the parent molecule 1. Furthermore thioacylal 2a can be considered as a promising trypanocidal agent. (C) 2010 Elsevier Masson SAS. All rights reserved.