(2R,3R)-4-(N-benzyl-N'-tert-butyloxycarbonyl-hydrazino)-2-(4-bromobenzyloxy)-3-hydroxy-N-((1S,2R)-2-hydroxyindan-1-yl)-butyramide | 639839-83-1

• 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: (2R,3R)-4-(N-benzyl-N'-tert-butyloxycarbonyl-hydrazino)-2-(4-bromobenzyloxy)-3-hydroxy-N-((1S,2R)-2-hydroxyindan-1-yl)-butyramide
• CAS: 639839-83-1
• 化学式: C₃₂H₃₈BrN₃O₆
• 分子量: 640.574
• InChiKey: OMSLHHUBRPXXQS-OVHUPFAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120.36
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-(N-benzyl-N'-tert-butyloxycarbonyl-hydrazino)-2-(4-bromobenzyloxy)-3-hydroxy-N-((1S,2R)-2-hydroxyindan-1-yl)-butyramide 在 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (2R,3R)-4-[N-benzyl-N'-((S)-2-benzyloxycarbonylamino-3-methyl-butyryl)-hydrazino]-2-(4-bromobenzyloxy)-3-hydroxy-N-((1S,2R)-2-hydroxy-indan-1-yl)-butyramide
  参考文献：
  名称：

  New inhibitors of the malaria aspartyl proteases plasmepsin I and II

  摘要：

  New inhibitors of plasmepsin I and II, the aspartic proteases of the malaria parasite Plasmodium falciparum, are described. From paralell solution phase chemistry, several reversed-statine type isostere inhibitors, many of which are aza-peptides, have been prepared. The synthetic strategy delivers the target compounds in good to high overall yields and with excellent stereochemical control throughout the developed route. The final products were tested for their plasmepsin I and 11 inhibiting properties and were found to exhibit modest but promising activity. The best inhibitor exhibits K-i values of 250 nM and 1.4 muM for Plm I and II, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00312-2
• 作为产物：
  描述：

  methyl (2R,3R)-2-(4-bromobenzyloxy)-3,4-dihydroxy-3,4-O-isopropylidene-butyrate 在 lithium hydroxide 、 Dowex H⁺ 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 7.75h， 生成 (2R,3R)-4-(N-benzyl-N'-tert-butyloxycarbonyl-hydrazino)-2-(4-bromobenzyloxy)-3-hydroxy-N-((1S,2R)-2-hydroxyindan-1-yl)-butyramide
  参考文献：
  名称：

  New inhibitors of the malaria aspartyl proteases plasmepsin I and II

  摘要：

  New inhibitors of plasmepsin I and II, the aspartic proteases of the malaria parasite Plasmodium falciparum, are described. From paralell solution phase chemistry, several reversed-statine type isostere inhibitors, many of which are aza-peptides, have been prepared. The synthetic strategy delivers the target compounds in good to high overall yields and with excellent stereochemical control throughout the developed route. The final products were tested for their plasmepsin I and 11 inhibiting properties and were found to exhibit modest but promising activity. The best inhibitor exhibits K-i values of 250 nM and 1.4 muM for Plm I and II, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00312-2