tert-butyl ((1S,2S)-3-((R)-2-((tert-butoxycarbonyl)amino)-3-mercaptopropanamido)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl)carbamate | 1335122-96-7

• 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: tert-butyl ((1S,2S)-3-((R)-2-((tert-butoxycarbonyl)amino)-3-mercaptopropanamido)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl)carbamate
• CAS: 1335122-96-7
• 化学式: C₂₂H₃₄N₄O₈S
• 分子量: 514.6
• InChiKey: LITGXNFOUSOTGZ-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  169.13
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((1S,2S)-3-((R)-2-((tert-butoxycarbonyl)amino)-3-mercaptopropanamido)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl)carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以54%的产率得到(R)-2-amino-N-((2S,3S)-2-amino-3-hydroxy-3-(4-nitrophenyl)propyl)-3-mercaptopropanamide hydrochloride
  参考文献：
  名称：

  Novel aminopeptidase N (APN/CD13) inhibitors derived from chloramphenicol amine

  摘要：

  Aminopeptidase N (APN) is involved in different physiological and pathological processes of tumor cells, including proliferation, invasion, apoptosis and metastasis. Herein one series of compounds derived from commercially available (1S, 2S)-2-amino-1-(4-nitrophenyl) propane-1,3-diol have been designed and synthesized. Furthermore, preliminary activity evaluation showed that some compounds elicited moderate inhibitory activity against APN with compounds 10e (IC50 = 6.1 +/- 0.5 mu M) possessing the best efficacy, which could be used as the lead compound in the future for anticancer agents research. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.008
• 作为产物：
  描述：

  tert-butyl ((1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)carbamate 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 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 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.5h， 生成 tert-butyl ((1S,2S)-3-((R)-2-((tert-butoxycarbonyl)amino)-3-mercaptopropanamido)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl)carbamate
  参考文献：
  名称：

  Novel aminopeptidase N (APN/CD13) inhibitors derived from chloramphenicol amine

  摘要：

  Aminopeptidase N (APN) is involved in different physiological and pathological processes of tumor cells, including proliferation, invasion, apoptosis and metastasis. Herein one series of compounds derived from commercially available (1S, 2S)-2-amino-1-(4-nitrophenyl) propane-1,3-diol have been designed and synthesized. Furthermore, preliminary activity evaluation showed that some compounds elicited moderate inhibitory activity against APN with compounds 10e (IC50 = 6.1 +/- 0.5 mu M) possessing the best efficacy, which could be used as the lead compound in the future for anticancer agents research. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.008