2-(2-cyanoethyl)-7-<(1,1-dimethylethoxy)carbonyl>-2,7,11-triazadodecanedioic acid bis(1,1-dimethylethyl) ester | 128550-03-8

• 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: 2-(2-cyanoethyl)-7-<(1,1-dimethylethoxy)carbonyl>-2,7,11-triazadodecanedioic acid bis(1,1-dimethylethyl) ester
• 英文别名: tert-butyl N-(2-cyanoethyl)-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
• CAS: 128550-03-8
• 化学式: C₂₅H₄₆N₄O₆
• 分子量: 498.663
• InChiKey: OCIXSAHDFCNRTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  612.2±55.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-cyanoethyl)-7-<(1,1-dimethylethoxy)carbonyl>-2,7,11-triazadodecanedioic acid bis(1,1-dimethylethyl) ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 29.5h， 生成 tert-butyl (3-((tert-butoxycarbonyl)(3-((2-cyanoethyl)amino)propyl)amino)propyl)(4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)carbamate
  参考文献：
  名称：

  Jasys, V. John; Kelbaugh, Paul B.; Nason, Deane M., Journal of the American Chemical Society, 1990, vol. 112, # 18, p. 6696 - 6704

  摘要：

  DOI：
• 作为产物：
  描述：

  16-cyano-2,2-dimethyl-3-oxa-4-oxo-5,9,14-triazahexadecane 生成 2-(2-cyanoethyl)-7-<(1,1-dimethylethoxy)carbonyl>-2,7,11-triazadodecanedioic acid bis(1,1-dimethylethyl) ester
  参考文献：
  名称：

  JASYS, V. JOHN;KELBAUGH, PAUL R.;NASON, DEANE M.;PHILLIPS, DOUGLAS;ROSNAC+, J. AMER. CHEM. SOC., 112,(1990) N8, C. 6696-6704

  摘要：

  DOI：

文献信息

• Polyaminoquinoline Iron Chelators for Vectorization of Antiproliferative Agents: Design, Synthesis, and Validation
  作者：Vincent Corcé、Emmanuelle Morin、Solène Guihéneuf、Eric Renault、Stéphanie Renaud、Isabelle Cannie、Raphaël Tripier、Luís M. P. Lima、Karine Julienne、Sébastien G. Gouin、Olivier Loréal、David Deniaud、François Gaboriau

  DOI：10.1021/bc300324c

  日期：2012.9.19

  Iron chelation in tumoral cells has been reported as potentially useful during antitumoral treatment. Our aim was to develop new polyaminoquinoline iron chelators targeting tumoral cells. For this purpose, we designed, synthesized, and evaluated the biological activity of a new generation of iron chelators, which we named Quilamines, based on an 8-hydroxyquinoline (8-HQ) scaffold linked to linear polyamine vectors. These were designed to target tumor cells expressing an overactive polyamine transport system (PTS). A set of Quilamines bearing variable polyamine chains was designed and assessed for their ability to interact with iron. Quilamines were also screened for their cytostatic/cytotoxic effects and their selective uptake by the PTS in the CHO cell line. Our results show that both the 8-HQ moiety and the polyamine part participate in the iron coordination. HQ1-44, the most promising Quilamine identified, presents a homospermidine moiety and was shown to be highly taken up by the PTS and to display an efficient antiproliferative activity that occurred in the micromolar range. In addition, cytotoxicity was only observed at concentrations higher than 100 mu M. We also demonstrated the high complexation capacity of HQ1-44 with iron while much weaker complexes were formed with other cations, indicative of a high selectivity. We applied the density functional theory to study the binding energy and the electronic structure of prototypical iron(III)-Quilamine complexes. On the basis of these calculations, Quilamine HQ1-44 is a strong tridentate ligand for iron(III) especially in the form of a 1:2 complex.
• JASYS, V. JOHN;KELBAUGH, PAUL R.;NASON, DEANE M.;PHILLIPS, DOUGLAS;ROSNAC+, J. AMER. CHEM. SOC., 112,(1990) N8, C. 6696-6704
  作者：JASYS, V. JOHN、KELBAUGH, PAUL R.、NASON, DEANE M.、PHILLIPS, DOUGLAS、ROSNAC+

  DOI：——

  日期：——
• Jasys, V. John; Kelbaugh, Paul B.; Nason, Deane M., Journal of the American Chemical Society, 1990, vol. 112, # 18, p. 6696 - 6704
  作者：Jasys, V. John、Kelbaugh, Paul B.、Nason, Deane M.、Phillips, Douglas、Rosnack, Kenneth J.、Saccomano, Nicholas A.、Stroh, Justin G.、Volkmann, Robert A.

  DOI：——

  日期：——