1,6,13-triazacyclononadecane [6,6,4] | 652130-90-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,6,13-triazacyclononadecane [6,6,4]
• 英文别名: 1,6,13-triazacyclononadecane；1,6,13-Triazacyclononadecane
• CAS: 652130-90-0
• 化学式: C₁₆H₃₅N₃
• 分子量: 269.474
• InChiKey: MSZCGVLDROCZTD-UHFFFAOYSA-N

物化性质

• 沸点：
  404.3±13.0 °C(Predicted)
• 密度：
  0.828±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 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：
  36.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,6,13-triazacyclononadecane [6,6,4] 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 生成 1,6,13-tris(2-chloroethyl)-1,6,13-triazacyclononadecane trihydrochloride
  参考文献：
  名称：

  Synthesis of novel DNA cross-linking antitumour agents based on polyazamacrocycles

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.01.055
• 作为产物：
  描述：

  1,6,13-tris-(2-(trimethylsilyl)ethanesulfonyl)-1,6,13-triazacycloheptadecane [6,6,4] 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以31%的产率得到1,6,13-triazacyclononadecane [6,6,4]
  参考文献：
  名称：

  A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)

  摘要：

  SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.067

文献信息

• A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)
  作者：Laurie L Parker、Nicholas D Gowans、Stephen W Jones、David J Robins

  DOI：10.1016/j.tet.2003.10.067

  日期：2003.12

  SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.