1,4,7,12,15,18-hexaazacyclodocosane | 58512-71-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,4,7,12,15,18-hexaazacyclodocosane
• 英文别名: 1,4,7,12,15,18-Hexazacyclodocosane
• CAS: 58512-71-3
• 化学式: C₁₆H₃₈N₆
• 分子量: 314.518
• InChiKey: ZKPLZVRLEMPGOX-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  496.9±45.0 °C(Predicted)
• 密度：
  0.858±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.2
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {rhodium(OAc)(1,5-cyclooctadiene)}2 、 1,4,7,12,15,18-hexaazacyclodocosane 在 苯 作用下， 以 苯 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Binuclear rhodium(I) complexes. Synthesis of [Rh(COD)]2L(OAc)2 where L is the new 22-membered macromonocycle 1,4,7,12,15,18-hexaazacyclodocosane

  摘要：

  DOI：

  10.1016/s0022-328x(00)85792-7
• 作为产物：
  描述：

  1,4,7,12,15,18-hexakis(p-tolylsulfonyl)-1,4,7,12,15,18-hexaazacyclodocosane 在 氢溴酸 、 溶剂黄146 、 苯酚 作用下， 反应 30.0h， 以78%的产率得到1,4,7,12,15,18-hexaazacyclodocosane
  参考文献：
  名称：

  磷酰基转移的超分子催化：大环多胺介导的乙酰磷酸合成焦磷酸的共催化

  摘要：

  L'hexaaza-24-crown-8 催化 l'hydrolyse du phosphate d'acete en orthophosphate et la 合成脱二磷酸盐

  DOI：

  10.1021/ja00257a024

文献信息

• General synthetic route to hexaamine macrocycles
  作者：Andrea E. Martin、John E. Bulkowski

  DOI：10.1021/jo00342a007

  日期：1982.1
• Synthesis of novel DNA cross-linking antitumour agents based on polyazamacrocycles
  作者：Laurie L. Parker、Fiona M. Anderson、C. Caroline O’Hare、Stephen M. Lacy、John P. Bingham、David J. Robins、John A. Hartley

  DOI：10.1016/j.bmc.2005.01.055

  日期：2005.4

  We are seeking to develop more effective alkylating agents as antitumour agents. In previous work conformationally restricted nitrogen mustards were synthesised containing piperidine or pyrrolidine rings. The free bases were designed to be bifunctional alkylating agents via aziridinium ion formation and the effects of varying the distances between the two alkylating sites were studied. Some efficient cross-linkers of naked DNA were prepared but few of these compounds exhibited significant cytotoxicity in human tumour cells in vitro. We have extended this work by making tri- and tetra-azamacrocyclic compounds containing two to four potential alkylating sites. Most of these compounds were powerful DNA alkylating agents and showed cytotoxicity (IC(50) values 6-100 mu M) comparable with chlorambucil (45 mu M) and melphalan (8.5 mu M). In particular the cyclen derivative 2a was more than 10(4) times more effective at cross-linking DNA (2a XL(50) << 10 nM) than chlorambucil (XL(50) 100 mu M), and showed significant cytotoxicity in human tumour cells in vitro. (c) 2005 Elsevier Ltd. All rights reserved.
• MARTIN, A. E.;BULKOWSKI, J. E., J. ORG. CHEM., 1982, 47, N 3, 415-418
  作者：MARTIN, A. E.、BULKOWSKI, J. E.

  DOI：——

  日期：——