[4-(benzylideneamino)butyl]carbamic acid tert-butyl ester | 378785-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-(benzylideneamino)butyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl (4-(benzylideneamino)butyl)carbamate；tert-butyl N-[4-(benzylideneamino)butyl]carbamate
• CAS: 378785-51-4
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: RALDKBBXVZTQNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4-(benzylideneamino)butyl]carbamic acid tert-butyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 tert-butyl 4-(benzylamino)butylcarbamate
  参考文献：
  名称：

  Synthetic Development of New 3-(4-Arylmethylamino)butyl-5-arylidene-rhodanines under Microwave Irradiation and Their Effects on Tumor Cell Lines and against Protein Kinases

  摘要：

  以商用 1,4-二氨基丁烷 1 为起始原料，通过六个步骤开发出了 3-(4-芳基甲基氨基)丁基-5-芳基亚甲基-2-硫酮-1,3-噻唑烷-4-酮 9 的新路线。这一多步骤合成的关键步骤是在微波介质的辅助下，采用溶液相 "一锅两步法"，从 N-（芳基甲基）丁烷-1,4-二胺盐酸盐 6a-f（作为第一点多样性的来源）和商用双（羧甲基）-三硫代碳酸酯试剂 7 开始，构建罗丹宁平台。在微波辐照下，该平台立即与一系列芳香醛 3（作为第二点多样性）通过克诺文纳格尔缩合作用实现了官能化。这些新化合物的制备收率从中等到良好，并获得了 14 个合成产物 9a-n，其外环双键具有 Z 几何结构。测试了这些新的 5-芳基罗丹宁衍生物 9a-n 对四种蛋白激酶的激酶抑制效力：这四种蛋白激酶是：人细胞周期蛋白依赖性激酶 5-p25（HsCDK5-p25）、猪糖原合成酶激酶 3（GSK-3α/β）、猪酪蛋白激酶 1（SsCK1）和人 HsHaspin。此外，还对这些化合物体外抑制细胞增殖的能力进行了评估（HuH7 D12、Caco 2、MDA-MB 231、HCT 116、PC3、NCI-H727、HaCat 和成纤维细胞）。在所有这些化合物中，9j 对 SsCK1 具有选择性微摩尔抑制活性，9i 在 HuH7 D12 和 MDA-MBD231 细胞系中具有抗肿瘤活性。

  DOI：

  10.3390/molecules200712412
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 magnesium sulfate 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 19.0h， 生成 [4-(benzylideneamino)butyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Polyamine functionalized carbon nanotubes: synthesis, characterization, cytotoxicity and siRNA binding

  摘要：

  在这项工作中，我们合成了一系列新型阳离子碳纳米管（CNTs）用于小干扰RNA（siRNA）的结合。通过添加或酰胺化反应，单壁和多壁碳纳米管均被改性，引入了包括腐胺、精胺和亚精胺在内的短链聚胺。所有新型共轭物均通过多种光谱和显微技术进行了表征。它们的细胞毒性在人肺癌癌细胞系上进行了评估。最后，我们分析了它们结合siRNA的能力，旨在开发用于基因沉默应用的新型载体。不同共轭物的分散性特性和结合siRNA的能力被发现强烈依赖于功能基团在碳纳米管上的位置（即主要在末端，通过酰胺化反应引入；或在侧壁上，通过直接C–C添加反应引入）。

  DOI：

  10.1039/c0jm04064a

文献信息

• Polyamine functionalized carbon nanotubes: synthesis, characterization, cytotoxicity and siRNA binding
  作者：Prabhpreet Singh、Cristian Samorì、Francesca Maria Toma、Cyrill Bussy、Antonio Nunes、Khuloud T. Al-Jamal、Cécilia Ménard-Moyon、Maurizio Prato、Kostas Kostarelos、Alberto Bianco

  DOI：10.1039/c0jm04064a

  日期：——

  In this work we have synthesized a new series of cationic carbon nanotubes (CNTs) for siRNA binding. Both single- and multi-walled CNTs have been modified by addition or amidation reaction with short linear polyamine chains including putrescine, spermidine and spermine. All the new conjugates have been characterized with several spectroscopic and microscopic techniques. Their cytotoxic effects have been assessed on human lung carcinoma cell line. Finally, we have analyzed their capacity to bind siRNA towards the development of new carriers for gene silencing applications. The dispersibility properties and the capacity to complex siRNA of the different conjugates were found to be strongly dependent on the position of the functional groups on CNTs (i.e. mainly at the tips following the amidation reaction or on the sidewalls by direct C–C addition).

  在这项工作中，我们合成了一系列新型阳离子碳纳米管（CNTs）用于小干扰RNA（siRNA）的结合。通过添加或酰胺化反应，单壁和多壁碳纳米管均被改性，引入了包括腐胺、精胺和亚精胺在内的短链聚胺。所有新型共轭物均通过多种光谱和显微技术进行了表征。它们的细胞毒性在人肺癌癌细胞系上进行了评估。最后，我们分析了它们结合siRNA的能力，旨在开发用于基因沉默应用的新型载体。不同共轭物的分散性特性和结合siRNA的能力被发现强烈依赖于功能基团在碳纳米管上的位置（即主要在末端，通过酰胺化反应引入；或在侧壁上，通过直接C–C添加反应引入）。
• Manganese‐Catalyzed Selective Hydrogenative Cross‐Coupling of Nitriles and Amines to Form Secondary Imines
  作者：Xiao‐Gen Li、Qi‐Lin Zhou

  DOI：10.1002/adsc.202100285

  日期：2021.7.20

  Manganese complexes with tridentate PNN ligands have been synthesized as catalysts for hydrogenative cross-coupling reaction of nitriles and amines to form secondary imines. This reaction afforded a variety of unsymmetrical secondary imines in good yields with excellent selectivity. Investigation of catalyst intermediates indicated that an amido manganese complex may be the active catalyst species

  已合成具有三齿 PNN 配体的锰配合物作为腈和胺的氢化交叉偶联反应形成仲亚胺的催化剂。该反应以良好的收率和优异的选择性提供了多种不对称仲亚胺。对催化剂中间体的研究表明，酰氨基锰配合物可能是该反应的活性催化剂。
• A one-pot selective synthesis of N-Boc protected secondary amines: tandem direct reductive amination/N-Boc protection
  作者：Raghupathi Neelarapu、Pavel A. Petukhov

  DOI：10.1016/j.tet.2012.06.055

  日期：2012.9

  A one-pot tandem direct reductive amination of aldehydes with primary amines resulting in N-Boc secondary amines using a (Boc)(2)O/sodium triacetoxyborohydride (STAB) system is reported. The tandem procedure is efficient, selective, and versatile, giving excellent yields of N-Boc protected secondary amines even in those cases where the products are prone to intramolecular lactamization. (C) 2012 Elsevier Ltd. All rights reserved.
• ——
  作者：Scott T. Moe、Daryl L. Smith、Yongwei (Eric) Chien、Joanna L. Raszkiewicz、Linda D. Artman、Alan L. Mueller

  DOI：10.1023/a:1011988317683

  日期：——

  Purpose. Twelve synthetic spider toxin analogs were prepared in an effort to better understand the structure-activity relationships of the polyamine portion of argiotoxin-636 (Arg-636), a noncompetitive NMDA receptor (NMDAR) antagonist.Methods. The 1,13-diamino-4,8-diazatridecane portion of the side chain of Arg-636 was systematically modified in an effort to further our knowledge of the structural requirements for the alkyl linker spacing between the amine nitrogens. Systematic isosteric replacement of each of the amine nitrogens in the polyamine moiety with either oxygen or carbon provided a series of compounds which were evaluated in vitro for NMDAR antagonist activity.Results. One-half of the heteroatoms found in Arg-636 were removed to provide analogs which maintained in vitro potency below 1 mu M. However, these simplified analogs produced similar or more pronounced effects on the cardiovascular system than Arg-636 in vivo.Conclusions. In this set of analogs, a minimum of three basic nitrogens in the side chain was required for maximum potency as NMDAR antagonists. Isosteric nitrogen substitutions in the polyamine chain reduced the in vitro potency of these analogs. An analog binding-conformation model was proposed to rationalize the inactivity of these isosterically substituted analogs.
• Synthetic Development of New 3-(4-Arylmethylamino)butyl-5-arylidene-rhodanines under Microwave Irradiation and Their Effects on Tumor Cell Lines and against Protein Kinases
  作者：Camille Dago、Christelle Ambeu、Wacothon-Karime Coulibaly、Yves-Alain Békro、Janat Mamyrbékova、Audrey Defontaine、Blandine Baratte、Stéphane Bach、Sandrine Ruchaud、Rémy Guével、Myriam Ravache、Anne Corlu、Jean-Pierre Bazureau

  DOI：10.3390/molecules200712412

  日期：——

  A new route to 3-(4-arylmethylamino)butyl-5-arylidene-2-thioxo-1,3-thiazolidine-4-one 9 was developed in six steps from commercial 1,4-diaminobutane 1 as starting material. The key step of this multi-step synthesis involved a solution phase “one-pot two-steps” approach assisted by microwave dielectric from N-(arylmethyl)butane-1,4-diamine hydrochloride 6a–f (as source of the first point diversity) and commercial bis-(carboxymethyl)-trithiocarbonate reagent 7 for construction of the rhodanine platform. This platform was immediately functionalized by Knoevenagel condensation under microwave irradiation with a series of aromatic aldehydes 3 as second point of diversity. These new compounds were prepared in moderate to good yields and the fourteen synthetic products 9a–n have been obtained with a Z-geometry about their exocyclic double bond. These new 5-arylidene rhodanines derivatives 9a–n were tested for their kinase inhibitory potencies against four protein kinases: Human cyclin-dependent kinase 5-p25, HsCDK5-p25; porcine Glycogen Synthase Kinase-3, GSK-3α/β; porcine Casein Kinase 1, SsCK1 and human HsHaspin. They have also been evaluated for their in vitro inhibition of cell proliferation (HuH7 D12, Caco 2, MDA-MB 231, HCT 116, PC3, NCI-H727, HaCat and fibroblasts). Among of all these compounds, 9j presented selective micromolar inhibition activity on SsCK1 and 9i exhibited antitumor activities in the HuH7 D12, MDA-MBD231 cell lines.

  以商用 1,4-二氨基丁烷 1 为起始原料，通过六个步骤开发出了 3-(4-芳基甲基氨基)丁基-5-芳基亚甲基-2-硫酮-1,3-噻唑烷-4-酮 9 的新路线。这一多步骤合成的关键步骤是在微波介质的辅助下，采用溶液相 "一锅两步法"，从 N-（芳基甲基）丁烷-1,4-二胺盐酸盐 6a-f（作为第一点多样性的来源）和商用双（羧甲基）-三硫代碳酸酯试剂 7 开始，构建罗丹宁平台。在微波辐照下，该平台立即与一系列芳香醛 3（作为第二点多样性）通过克诺文纳格尔缩合作用实现了官能化。这些新化合物的制备收率从中等到良好，并获得了 14 个合成产物 9a-n，其外环双键具有 Z 几何结构。测试了这些新的 5-芳基罗丹宁衍生物 9a-n 对四种蛋白激酶的激酶抑制效力：这四种蛋白激酶是：人细胞周期蛋白依赖性激酶 5-p25（HsCDK5-p25）、猪糖原合成酶激酶 3（GSK-3α/β）、猪酪蛋白激酶 1（SsCK1）和人 HsHaspin。此外，还对这些化合物体外抑制细胞增殖的能力进行了评估（HuH7 D12、Caco 2、MDA-MB 231、HCT 116、PC3、NCI-H727、HaCat 和成纤维细胞）。在所有这些化合物中，9j 对 SsCK1 具有选择性微摩尔抑制活性，9i 在 HuH7 D12 和 MDA-MBD231 细胞系中具有抗肿瘤活性。