3-amino-2-(benzyloxy)-1-propanol | 136185-94-9

• 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: 3-amino-2-(benzyloxy)-1-propanol
• 英文别名: 3-Amino-2-phenylmethoxypropan-1-ol
• CAS: 136185-94-9
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: KKTAXIKAWJBOCX-UHFFFAOYSA-N

物化性质

• 沸点：
  328.9±27.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-2-(benzyloxy)-1-propanol 、 双(2-氯乙基)氨基磷酰二氯 生成 (5S)-N,N-bis(2-chloroethyl)-2-oxo-5-phenylmethoxy-1,3,2λ5-oxazaphosphinan-2-amine
  参考文献：
  名称：

  EIBL, H.;KOLAR, C.;SEILER, F. R.;SEDLACEK, H. -H.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Azido-2-benzyloxy-propan-1-ol 生成 3-amino-2-(benzyloxy)-1-propanol
  参考文献：
  名称：

  EIBL, H.;KOLAR, C.;SEILER, F. R.;SEDLACEK, H. -H.

  摘要：

  DOI：

文献信息

• Neue Cyclophosphamid-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP0072531A1

  公开（公告）日：1983-02-23

  Die Erfindung betrifft neue Cyclophosphamid-Derivate der Formel I worin R ein Wasserstoffatom, einen Kohlenwasserstoffrest oder einen heterocyclischen Rest bedeutet. Die neuen Verbindungen zeigen eine dem Cyclophosphamid vergleichbare zytostatische Wirksamkeit bei einer wesentlich geringeren Toxizität.

  本发明涉及式 I 的新型环磷酰胺衍生物。 其中 R 是氢原子、烃基或杂环基。这些新化合物具有与环磷酰胺相当的细胞抑制效力，但毒性大大降低。
• Synthesis and antitumor properties of activated cyclophosphamide analogs
  作者：Richard F. Borch、Gregory W. Canute

  DOI：10.1021/jm00114a013

  日期：1991.10

  A series of 5- and 6-substituted cyclophosphamide analogues has been prepared, and their P-31 NMR kinetics of phosphoramide mustard (PDA) release and in vitro and in vivo cytotoxicity have been evaluated. cis-4-Hydroxy-5-methoxycyclophosphamide equilibrated very slowly and to a minor extent with the ring-opened aldophosphamide analogues in aqueous buffer; release of PDA was observed to a minor extent and only at high (1 M) buffer concentrations. This analogue was essentially inactive in vitro against L1210 and P388 leukemia cells. 6-Phenylcyclophosphamide and its 4-hydroperoxy derivative were potent inhibitors of blood acetylcholinesterase and were lethal at therapeutic doses in mice. In contrast, 4-hydroperoxy-6-(4-pyridyl)cyclophosphamide did not inhibit acetylcholinesterase and showed significant antitumor activity in vitro and in vivo against both wild-type and cyclophosphamide-resistant L1210 leukemia. The 4-hydroperoxy-6-arylcyclophosphamides were generally active in vitro against both wild-type and cyclophosphamide-resistant L1210 and P388 cells, and several analogues showed significant activity in vivo. Surprisingly, there was no correlation between antitumor activity in vitro and the rate of PDA release in aqueous buffer. Several compounds that showed essentially no release of PDA in aqueous buffer over several hours were highly cytotoxic to leukemia cells following a 1-h exposure in vitro. These results show that activated cyclophosphamide analogues substituted at the 6-position are not cross-resistant in these leukemia cell lines, and that a specific intracellular activation mechanism may be catalyzing PDA release in these analogues.