N,N'-bis<(tert-butyloxy)carbonyl>-1-amino-3-(aminooxy)-2-propanol | 139526-86-6

• 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: N,N'-bis<(tert-butyloxy)carbonyl>-1-amino-3-(aminooxy)-2-propanol
• 英文别名: N,N'-bis[(tert-butyloxy)carbonyl]-1-amino-3-(aminooxy)-2-propanol；tert-butyl N-[2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]oxypropyl]carbamate
• CAS: 139526-86-6
• 化学式: C₁₃H₂₆N₂O₆
• 分子量: 306.359
• InChiKey: ZKMHYYOWYADGOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis<(tert-butyloxy)carbonyl>-1-amino-3-(aminooxy)-2-propanol 在 盐酸 作用下， 以 乙醚 、 氯仿 为溶剂， 以80%的产率得到1-amino-3-(aminooxy)-2-propanol dihydrochloride
  参考文献：
  名称：

  Selective delivery of 2-hydroxy APA to Trypanosoma brucei using the melamine motif

  摘要：

  Trypanosoma brucei, the parasite that causes human African trypanosomiasis, is auxotrophic for purines and has specialist nucleoside transporters to import these metabolites. In particular, the P2 aminopurine transporter can also selectively accumulate melamine derivatives. In this Letter, we report the coupling of the melamine moiety to 2-hydroxy APA, a potent ornithine decarboxylase inhibitor, with the aim of selectively delivering this compound to the parasite. The best compound described here shows an increased in vitro trypanocidal activity compared with the parent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.070
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1-amino-3-(aminooxy)-2-propanol dihydrochloride 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以53.2%的产率得到N,N'-bis<(tert-butyloxy)carbonyl>-1-amino-3-(aminooxy)-2-propanol
  参考文献：
  名称：

  2-Substituted 3-(aminooxy)propanamines as inhibitors of ornithine decarboxylase: synthesis and biological activity

  摘要：

  1-Amino-3-(aminooxy)-2-propanol (6a) has been synthesized and found to inhibit rat liver ornithine decarboxylase (ODC) with an IC50 in the nanomolar range. Compound 6a served as a basis for the design of new enzyme inhibitors, which led to the identification of 3-(aminooxy)-2-fluoropropanamine (15) as a new powerful enzyme blocker. Compound 15 inhibited ODC at 3 times lower concentrations than 6a and 3-(aminooxy)propanamine (APA), and it was superior to APA as an antiproliferative agent in inhibiting the growth of human T24 bladder carcinoma cells in vitro.

  DOI：

  10.1021/jm00086a003