(3-tert-butoxycarbonylaminobutyl)-(2-cyanoethyl)carbamic acid tert-butyl ester | 147875-12-5

• 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: (3-tert-butoxycarbonylaminobutyl)-(2-cyanoethyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl 2-cyanoethyl-{3-[(tert-butoxycarbonyl)amino]propyl}carbamate；tert-butyl N-(2-cyanoethyl)-N-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate
• CAS: 147875-12-5
• 化学式: C₁₆H₂₉N₃O₄
• 分子量: 327.424
• InChiKey: QRSPEORJTHRDTK-UHFFFAOYSA-N

物化性质

• 沸点：
  465.8±38.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-tert-butoxycarbonylaminobutyl)-(2-cyanoethyl)carbamic acid tert-butyl ester 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 47.0h， 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：

  N-叔丁氧羰基-1,3-丙二胺 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (3-tert-butoxycarbonylaminobutyl)-(2-cyanoethyl)carbamic acid tert-butyl ester
  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

• Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation
  作者：Faiz Ahmed Khan、Saeed Ahmad、Naveena Kodipelli、Gururaj Shivange、Roy Anindya

  DOI：10.1039/c3ob42537a

  日期：——

  A–C are a novel class of bromotyrosine-derived antibacterial agents isolated recently from the marine sponge Suberea ianthelliformis. We have synthesized ianthelliformisamines A–C straightforwardly by the condensation of (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid and the corresponding Boc-protected polyamine followed by Boc-deprotection with TFA. Further, using this reaction protocol, a library

  Ianthelliformisamines A–C是一类新的从溴酪氨酸衍生的抗菌剂，最近从海洋海绵Suberea ianthelliformis中分离出来。我们通过（E的缩合直接合成了邻苯二甲胺）-3-（3,5-二溴-4-甲氧基苯基）丙烯酸和相应的Boc保护的多胺，然后用TFA进行Boc脱保护。此外，使用该反应方案，通过使用3-苯基丙烯酸衍生物和Boc保护的多胺链，通过这两个片段的不同组合（苯环取代，双键几何结构或链不同），合成了其类似物（39个类似物）的文库多胺链中央间隔基团的长度（以红色显示）。筛选所有合成的化合物（苯乙酰胺胺A–C及其类似物）对革兰氏阴性菌（大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌）的抗菌活性）株。苯乙酰胺胺A的所有合成类似物均对两种菌株（大肠杆菌和金黄色葡萄球菌）均显示出细菌生长抑制作用，MIC值在117.8–0.10μM范围内，而苯乙酰胺胺C的任何合成类似物以及母
• 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。
• Cyclophanes. VIII. Synthesis and DNA-Cleaving Activities of Novel Heterocyclophanes Containing Two 4,4'-Bithiazole Rings.
  作者：Hideaki SASAKI、Atsumi SUEHIRO、Yasuyuki NAKAMOTO

  DOI：10.1248/cpb.45.189

  日期：——

  The novel heterocyclophanes, 3, 6, 21, 24-tetraaza[8.8](2, 2')(4, 4'-bithiazolophane) (3a) and 3, 7, 22, 26-tetraaza-[9.9](2, 2')(4, 4'-bithiazolophane) (3b) were readily synthesized by the cyclization of 1, 4-dibromobutane-2, 3-dione with N, N'-bis(tert-butoxycarbonyl)ethylenediamine-N, N'-dipropionthioamide and N, N'-bis(tert-butoxycarbonyl)-trimethylenediamine-N, N'-dipropionthioamide, respectively, followed by acidic deprotection. Under physiological conditions, 3a and 3b at 5 μM showed considerable DNA-cleaving activities in the presence of Co(II) without any reducing agent.

  新型杂环烷 3, 6, 21, 24-四氮杂[8.8](2, 2')(4, 4'-bithiazolophane) (3a) 和 3, 7, 22, 26-四氮杂-[9.9](2，2')(4，4'-联噻唑烷)(3b) 是通过环化 1，4-二溴丁烷-2，3-二酮与 N，N'-双(叔丁氧羰基)乙二胺-N、N，N'-双（叔丁氧羰基）乙二胺-N，N'-二丙硫异酰胺和 N，N'-双（叔丁氧羰基）三亚甲基二胺-N，N'-二丙硫异酰胺环化，然后进行酸性脱保护。在生理条件下，5 μM 的 3a 和 3b 在没有任何还原剂的情况下，在 Co(II) 存在下显示出相当大的 DNA 切断活性。
• Polyamine-Metal Chelator Conjugates
  申请人：Bergeron Raymond

  公开号：US20080096974A2

  公开（公告）日：2008-04-24

  Many metal chelators have polar or charged functional groups, which render them difficult to transport across a cell membrane. Polyamine-metal chelator conjugates of the invention are compounds comprising a first moiety which is a metal chelator and a second moiety which is a polyamine, where the polyamine moiety includes three or more nitrogen atoms which are capable of being positively charged at physiological pH. A spermine-L1 conjugate has been shown to accumulate in L1210 cells several hundred fold more than the unconjugated L1 chelator.

  许多金属螯合剂具有极性或带电的功能基团，这使得它们难以跨越细胞膜。本发明的多胺-金属螯合剂共轭物是化合物，包括第一部分是金属螯合剂，第二部分是多胺，其中多胺部分包括三个或更多的氮原子，在生理pH下能够呈正电荷。已经证明精胺-L1共轭物在L1210细胞中的积累比未共轭的L1螯合剂高出数百倍。
• 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.