N,N-dibenzyl-2-azido-ethylamine

• 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: N,N-dibenzyl-2-azido-ethylamine
• 英文别名: 2-azido-N,N-dibenzylethanamine；(2-azido-ethyl)-dibenzyl-amine；(2-Azido-aethyl)-dibenzyl-amin
• 化学式: C₁₆H₁₈N₄
• 分子量: 266.346
• InChiKey: WABNGGAPHNQGKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-chloro-N-(prop-2-yn-1-yl)quinolin-4-amine 、 N,N-dibenzyl-2-azido-ethylamine 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到7-chloro-N-({1-[2-(dibenzylamino)ethyl]-1H-1,2,3-triazol-4-yl}methyl)quinolin-4-amine
  参考文献：
  名称：

  In vitro antiplasmodial activity of triazole-linked chloroquinoline derivatives synthesized from 7-chloro-N-(prop-2-yn-1-yl)quinolin-4-amine

  摘要：

  The synthesis and in vitro evaluation of novel triazole-linked chloroquinoline derivatives as potential antiplasmodial agents against Plasmodium falciparum is reported. The 15 synthesized target compounds were obtained by means of a copper(I)-mediated click reaction between a variety of 1,2- and 1,3-azidoamines and 7-chloro-N-(prop-2-yn-1-yl) quinolin-4-amine in moderate to good yields (53-85%). The compounds were screened for antiplasmodial activity against NF54 chloroquine-sensitive and Dd2 chloroquine-resistant strains, alongside chloroquine and artesunate as reference compounds. Six of the test compounds revealed a 3-5 fold increase in antiplasmodial activity against chloroquine-resistant strain Dd2 compared to chloroquine. Among the six compounds with good antiplasmodial activity, a reduced cross-resistance relative to artesunate (>3 fold in comparison to chloroquine) was observed, mainly in derivatives that incorporated chloroquine-resistance reversing pharmacophores. A general trend for reduced chloroquine cross-resistance was also detected among 12 out of the 15 compounds tested. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.044
• 作为产物：
  描述：

  地苯那明 在 sodium azide 作用下， 生成 N,N-dibenzyl-2-azido-ethylamine
  参考文献：
  名称：

  Nosek et al., Chemicke Listy, 1952, vol. 46, p. 672

  摘要：

  DOI：

文献信息

• Iron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides
  作者：Yi-Dan Du、Cong-Ying Zhou、Wai-Pong To、Hai-Xu Wang、Chi-Ming Che

  DOI：10.1039/d0sc00784f

  日期：——

  strategy for the design of C–N bond formation reactions under mild reaction conditions, the challenge being lack of selectivity as a free nitrene reactive intermediate is usually involved. Herein is described an iron(III) porphyrin catalysed sp3 C–H amination and alkene aziridination with selectivity by using organic azides as the nitrogen source under blue LED light (469 nm) irradiation. The photochemical

  在温和的反应条件下，可见光驱动的有机叠氮化物的氮烯转移和插入反应是设计C–N键形成反应的一种有吸引力的策略，因为通常涉及游离的腈反应性中间体，因此缺乏选择性的挑战。本文描述了铁（III）卟啉催化的sp 3通过使用有机叠氮化物作为氮源，在蓝色LED光（469 nm）照射下，进行C–H胺化和烯烃的叠氮化。光化学反应显示化学选择性和区域选择性，并且对于复杂的天然和生物活性化合物的后期功能化有效。机理研究表明，卟啉铁既起光敏剂的作用，又起催化剂的作用，产生了反应性的铁-氮化物中间体，随后形成C-N键。
• In vitro antiplasmodial activity of triazole-linked chloroquinoline derivatives synthesized from 7-chloro-N-(prop-2-yn-1-yl)quinolin-4-amine
  作者：Lebusetsa Taleli、Carmen de Kock、Peter J. Smith、Stephen C. Pelly、Margaret A.L. Blackie、Willem A.L. van Otterlo

  DOI：10.1016/j.bmc.2015.06.044

  日期：2015.8

  The synthesis and in vitro evaluation of novel triazole-linked chloroquinoline derivatives as potential antiplasmodial agents against Plasmodium falciparum is reported. The 15 synthesized target compounds were obtained by means of a copper(I)-mediated click reaction between a variety of 1,2- and 1,3-azidoamines and 7-chloro-N-(prop-2-yn-1-yl) quinolin-4-amine in moderate to good yields (53-85%). The compounds were screened for antiplasmodial activity against NF54 chloroquine-sensitive and Dd2 chloroquine-resistant strains, alongside chloroquine and artesunate as reference compounds. Six of the test compounds revealed a 3-5 fold increase in antiplasmodial activity against chloroquine-resistant strain Dd2 compared to chloroquine. Among the six compounds with good antiplasmodial activity, a reduced cross-resistance relative to artesunate (>3 fold in comparison to chloroquine) was observed, mainly in derivatives that incorporated chloroquine-resistance reversing pharmacophores. A general trend for reduced chloroquine cross-resistance was also detected among 12 out of the 15 compounds tested. (C) 2015 Elsevier Ltd. All rights reserved.
• Nosek et al., Chemicke Listy, 1952, vol. 46, p. 672
  作者：Nosek et al.

  DOI：——

  日期：——