tert-butyl (1S,2S)-3-amino-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate | 1186120-59-1

• 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: tert-butyl (1S,2S)-3-amino-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate
• 英文别名: tert-butyl N-[(1S,2S)-3-amino-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]carbamate
• CAS: 1186120-59-1
• 化学式: C₁₄H₂₁N₃O₅
• 分子量: 311.338
• InChiKey: IJZRJHBKWDMDLS-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2S)-3-amino-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate 在 盐酸 、 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 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (S)-2,6-diamino-N-((2S,3S)-2-amino-3-hydroxy-3-(4-nitrophenyl)propyl)hexanamide 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：

  二碳酸二叔丁酯 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.5h， 生成 tert-butyl (1S,2S)-3-amino-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate
  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

文献信息

• Novel aminopeptidase N (APN/CD13) inhibitors derived from chloramphenicol amine
  作者：Meirong Jia、Kanghui Yang、Hao Fang、Yingying Xu、Siwei Sun、Li Su、Wenfang Xu

  DOI：10.1016/j.bmc.2011.07.008

  日期：2011.9

  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.