tert-butyl ((1S,2S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-1-hydroxy-1-(4-iodophenyl)propan-2-yl)carbamate | 1335122-61-6

• 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-((S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-1-hydroxy-1-(4-iodophenyl)propan-2-yl)carbamate
• CAS: 1335122-61-6
• 化学式: C₂₈H₃₈IN₃O₇
• 分子量: 655.53
• InChiKey: LEFHYGPVAHWSFQ-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  146.22
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((1S,2S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-1-hydroxy-1-(4-iodophenyl)propan-2-yl)carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以92%的产率得到(S)-2-amino-N-((2S,3S)-2-amino-3-hydroxy-3-(4-iodophenyl)propyl)-3-(4-hydroxyphenyl)propanamide 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)-3-amino-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate 在 iron(III) chloride hexahydrate 、 甲烷 、 1-羟基苯并三唑 、 对甲苯磺酸 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 potassium iodide 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 tert-butyl ((1S,2S)-3-((S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-1-hydroxy-1-(4-iodophenyl)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