N¹-tert-butoxycarbonyl-N³-(2-cyanoethyl)-1,3-propanediamine | 181780-44-9

• 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: N¹-tert-butoxycarbonyl-N³-(2-cyanoethyl)-1,3-propanediamine
• 英文别名: tert-butyl 3-(2-cyanoethylamino)propylcarbamate；tert-butyl N-[3-(2-cyanoethylamino)propyl]carbamate
• CAS: 181780-44-9
• 化学式: C₁₁H₂₁N₃O₂
• 分子量: 227.307
• InChiKey: CEHZXSOSSOLLLS-UHFFFAOYSA-N

物化性质

• 沸点：
  389.3±27.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹-tert-butoxycarbonyl-N³-(2-cyanoethyl)-1,3-propanediamine 在 盐酸 、 lithium aluminium tetrahydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 N¹-(3-aminopropyl)-N³-octadecylpropane-1,3-diamine
  参考文献：
  名称：

  CO2-switchable wormlike micelles

  摘要：

  以 C18 尾聚胺表面活性剂为基础，开发出了一种蠕虫状胶束系统，该系统在二氧化碳和氮气的交替处理下会发生完全可逆、可重复的 "溶胶-凝胶 "转变。

  DOI：

  10.1039/c3cc41059e
• 作为产物：
  描述：

  二碳酸二叔丁酯 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 40.0h， 生成 N¹-tert-butoxycarbonyl-N³-(2-cyanoethyl)-1,3-propanediamine
  参考文献：
  名称：

  CO2-switchable wormlike micelles

  摘要：

  以 C18 尾聚胺表面活性剂为基础，开发出了一种蠕虫状胶束系统，该系统在二氧化碳和氮气的交替处理下会发生完全可逆、可重复的 "溶胶-凝胶 "转变。

  DOI：

  10.1039/c3cc41059e

文献信息

• Efficient Synthesis of Orthogonally Protected Spermidine and Norspermidine Derivatives
  作者：Ryszard Andruszkiewicz、Michał Radowski、Zbigniew Czajgucki

  DOI：10.1081/scc-200054211

  日期：2005.4.1

  Abstract Several orthogonally protected spermidine and norspermidine derivatives have been synthesized via cyanoethylation of monoprotected 1,4‐butanediamine (putrescine) or 1,3‐propanediamine followed by protection of their secondary amino groups and final reduction of the nitriles with lithium aluminum hydride in etheral solution at 0°C, thus affording protected norspermidine or spermidine that may

  摘要 通过单保护的 1,4-丁二胺（腐胺）或 1,3-丙二胺的氰乙基化，然后保护它们的仲氨基，最后在醚溶液中用氢化铝锂还原腈类，合成了几种正交保护的亚精胺和去甲精胺衍生物。在0°C，从而提供可用于合成多胺酰胺或可进一步官能化的受保护的去甲精胺或亚精胺。
• Design and Synthesis of [2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)- ethyl]phosphonic Acid (EAA-090), a Potent <i>N</i>-Methyl-<scp>d</scp>-aspartate Antagonist, via the Use of 3-Cyclobutene-1,2-dione as an Achiral α-Amino Acid Bioisostere
  作者：William A. Kinney、Magid Abou-Gharbia、Deanna T. Garrison、Jean Schmid、Dianne M. Kowal、Donna R. Bramlett、Tracy L. Miller、Rene P. Tasse、Margaret M. Zaleska、John A. Moyer

  DOI：10.1021/jm970504g

  日期：1998.1.1

  that the two-carbon side chain length was optimum for NMDA receptor affinity. Substitution on the ring was found to be counterproductive in the case of sterically demanding dimethyl groups and of no consequence in the case of an H-bonding hydroxyl group. Replacement of the phosphonic acid group by either a carboxylic acid or a tetrazole group was unproductive. The potent bicyclic NMDA antagonists were

  二氮杂双环氨基酸膦酸酯15 [2-（8,9-dioxo-2,6-diazabicyclo [5.2.0] non-1（7）-en-2-yl）ethyl]膦酸被确定为有效的NMDA拮抗剂。它包含α-氨基酸生物甾体3,4-二氨基-3-环丁烯-1,2-二酮和一个用于构象刚性的附加环。在[3H] CPP结合测定，受激[3H] TCP结合测定和NMDA诱导的小鼠致死性模型中，化合物15与CGS-19755（5）一样有效。在大鼠大脑中动脉永久闭塞后，静脉内单次推注剂量的化合物15使梗塞组织的大小减少了57％。结构-活性关系（SAR）研究表明六元和八元环衍生物的活性降低，并且两个碳的侧链长度最适合NMDA受体的亲和力。发现在空间上需要二甲基的情况下，环上的取代会适得其反，而在氢键结合的羟基的情况下则无济于事。用羧酸或四唑基团取代膦酸基是无用的。有效的双环NMDA拮抗剂有效地合成了他们的非手性性质和容易从
• Facile Synthetic Route to Selectively Protected Spermidine Homologues
  作者：Ryszard Andruszkiewicz、Ewa Gronek、Jolanta Hałuszczak

  DOI：10.1080/00397910701845431

  日期：2008.2.1

  Abstract Several selectively protected spermidine homologues were synthesized via cyanoethylation reaction of monoprotected diamines, subsequent protection of their secondary amino group, hydrolysis of nitrile to primary amide function, and final Hofmann degradation of amides to amines with the aid of iodosobenzene diacetate (PIDA). The protected spermidine homologues may be directly used in the synthesis

  摘要 通过单保护二胺的氰乙基化反应、仲氨基的后续保护、腈水解为伯酰胺官能团以及酰胺在二乙酸碘苯酯 (PIDA) 的帮助下最终霍夫曼降解为胺，合成了几种选择性保护的亚精胺同系物。受保护的亚精胺同系物可直接用于多胺酰胺的合成或可进一步官能化。
• Arasujo, M. Joso S. M. P.; Ragnarsson, Ulf; Trigo, M. Joaquina S. A. Amaral, Journal of Chemical Research, Miniprint, 1996, # 8, p. 2143 - 2161
  作者：Arasujo, M. Joso S. M. P.、Ragnarsson, Ulf、Trigo, M. Joaquina S. A. Amaral、Almeida, M. Lurdes S.

  DOI：——

  日期：——
• 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.