tert-butyl (1,3-diazidopropan-2-yl)carbamate | 213475-73-1

• 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: tert-butyl (1,3-diazidopropan-2-yl)carbamate
• 英文别名: tert-butyl N-(1,3-diazidopropan-2-yl)carbamate
• CAS: 213475-73-1
• 化学式: C₈H₁₅N₇O₂
• 分子量: 241.253
• InChiKey: UIHBOBYKMDNQPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  67
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (1,3-diazidopropan-2-yl)carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以232 mg的产率得到2-甲基-2-丙基(1,3-二氨基-2-丙基)氨基甲酸酯
  参考文献：
  名称：

  化学合成的光学活性和正交保护的多胺的化学酶策略的发展。

  摘要：

  已经使用洋葱假单胞菌脂肪酶作为生物催化剂进行了一系列前手性2-取代-1,3-丙二胺的化学制备和立体选择性酶解对称。根据丙烷-1,3-二胺片段的C-2取代，具有不同等级的对映异构的新型光学活性的正交保护的二胺或三胺的合成首次获得。（S）-3-烯丙基-2-叔丁基-1-（9-芴基甲基）丙烷-1,2,3-三基三scarbamate的最终单选择脱保护反应使我们获得了一组新的对映异构体富集的二取代三胺化合物传统合成方法难以达到的效果。

  DOI：

  10.1016/j.tet.2009.08.001
• 作为产物：
  描述：

  2-((tert-butoxycarbonyl)amino)propane-1,3-diyl dimethanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 tert-butyl (1,3-diazidopropan-2-yl)carbamate
  参考文献：
  名称：

  Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates

  摘要：

  提供一种模块化策略，可以访问肽-Pt共轭物及其抗癌潜力的库。

  DOI：

  10.1039/c7nj03999a

文献信息

• Development of a chemoenzymatic strategy for the synthesis of optically active and orthogonally protected polyamines
  作者：Eduardo Busto、Vicente Gotor-Fernández、Jose Montejo-Bernardo、Santiago García-Granda、Vicente Gotor

  DOI：10.1016/j.tet.2009.08.001

  日期：2009.10

  stereoselective enzymatic desymmetrization of a series of prochiral 2-substituted-1,3-propanediamines have been carried out using Pseudomonas cepacia lipase as biocatalyst. Syntheses of novel optically active orthogonally protected di- or triamines have been achieved for the first time with different grade of enantiodiscrimination depending on the C-2 substitution of the propane-1,3-diamine fragment

  已经使用洋葱假单胞菌脂肪酶作为生物催化剂进行了一系列前手性2-取代-1,3-丙二胺的化学制备和立体选择性酶解对称。根据丙烷-1,3-二胺片段的C-2取代，具有不同等级的对映异构的新型光学活性的正交保护的二胺或三胺的合成首次获得。（S）-3-烯丙基-2-叔丁基-1-（9-芴基甲基）丙烷-1,2,3-三基三scarbamate的最终单选择脱保护反应使我们获得了一组新的对映异构体富集的二取代三胺化合物传统合成方法难以达到的效果。
• [EN] GUANIDINE-MODIFIED C-TERMINUS VANCOMYCIN COMPOUNDS, COMPOSITIONS AND METHODS<br/>[FR] COMPOSÉS DE VANCOMYCINE À EXTRÉMITÉ C-TERMINALE MODIFIÉE PAR DE LA GUANIDINE, COMPOSITIONS ET PROCÉDÉS
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2021216323A1

  公开（公告）日：2021-10-28

  A series of vancomycin C-terminus guanidine modifications are disclosed that improve antimicrobial activity, enhance the durability of antimicrobial action against selection or induction of resistance, and provide two synergistic mechanisms of action independent of D-Ala-D-Ala binding that cause inhibition of cell wall biosynthesis, while inducing bacterial cell permeability. A contemplated compound contains two combined peripheral modifications, a (4-chlorobiphenyl)methyl (CBP) and C-terminus guanidine modification, that provide new treatments against not only vancomycin-sensitive, but especially vancomycin- resistant bacteria. The data demonstrate that the synergistic behavior of the peripheral modifications requires the presence of both the CBP and guanidine modifications in a single molecule versus their combined use as an equimolar mixture of singly modified compounds. A prototypical member of the series, G3- CBP-vancomycin (15), exhibits no hemolytic activity, displays no mammalian cell growth inhibition, and possesses improved and especially attractive in vivo pharmacokinetic (PK) properties.

  披露了一系列万古霉素C-末端胍基修饰，可改善抗微生物活性，增强抗微生物作用对抗选择或诱导耐药性的耐久性，并提供两种独立于D-Ala-D-Ala结合的协同作用机制，导致细胞壁生物合成的抑制，同时诱导细菌细胞渗透性。一个可考虑的化合物包含两个组合的外围修饰，即（4-氯联苯）甲基（CBP）和C-末端胍基修饰，可提供新的治疗方法，不仅针对万古霉素敏感的细菌，特别是针对万古霉素耐药菌。数据表明，外围修饰的协同行为需要在单个分子中同时存在CBP和胍基修饰，而不是将它们作为等摩尔混合物的单一修饰化合物的组合使用。该系列的典型成员G3-CBP-万古霉素（15）不表现出溶血活性，不抑制哺乳动物细胞生长，并具有改进的特别有吸引力的体内药物动力学（PK）特性。
• 3-(Aminomethyl)piperazine-2,5-dione as a novel NMDA glycine site inhibitor from the chemical universe database GDB
  作者：Kong Thong Nguyen、Erika Luethi、Salahuddin Syed、Stephan Urwyler、Sonia Bertrand、Daniel Bertrand、Jean-Louis Reymond

  DOI：10.1016/j.bmcl.2009.04.021

  日期：2009.7

  Docking of randomly selected compounds from the chemical universe database GDB-11, which contains all organic molecules up to 11 atoms of C, N, O, F possible under consideration of simple chemical stability and synthetic feasibility rules, into the NMDA receptor glycine site (1pb7.pdb) lead to the identification of 3-(aminomethyl)piperazine-2,5-dione 3 and its close analog 5-(aminomethyl) piperazine-2,3dione 4 as possible new ligands for this drug target, which is implicated in synaptic plasticity, neuronal development, learning and memory. Synthesis of these compounds in 4 and 6 steps, respectively, and testing by radioligand displacement assays and electrophysiological measurements in Xenopus oocytes show that while 4 is inactive, 3 is indeed an inhibitor of glycine, with an estimated K-D of 50 mu M. (C) 2009 Elsevier Ltd. All rights reserved.
• Convenient and Simplified Approaches to N-Monoprotected Triaminopropane Derivatives: Key Intermediates for Bifunctional Chelating Agent Synthesis
  作者：Eric Benoist、Anthony Loussouarn、Patricia Remaud、Jean-François Chatal、Jean-François Gestin

  DOI：10.1055/s-1998-2128

  日期：1998.8
• Efficient and tunable synthesis of new polydentate bifunctional chelating agents using click chemistry
  作者：Clément Camp、Sandra Dorbes、Claude Picard、Eric Benoist

  DOI：10.1016/j.tetlet.2008.01.086

  日期：2008.3

  Two novel bifunctional chelating agents, which are bistriazole-based polyaminocarboxylic acids, have been designed and synthesised in high yields. An elegant synthetic approach using the Cu-catalysed azide-alkyne cycloaddition has been developed. This convenient route could be employed for the synthesis of a variety of polydentate bifunctional chelators. (c) 2008 Elsevier Ltd. All rights reserved.