ethyl 3-((benzyloxy)amino)propanoate

• 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: ethyl 3-((benzyloxy)amino)propanoate
• 英文别名: Ethyl 3-(phenylmethoxyamino)propanoate
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: UCKOLKPTQRVHKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-((benzyloxy)amino)propanoate 在 sodium hydroxide 、 1-羟基苯并三唑 、 达卡巴嗪 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 N-{3-[(tert-butoxycarbonyl)amino]propanoyl}-N-hydroxy-β-alanine
  参考文献：
  名称：

  Ferrioxamine B Analogues:  Targeting the FoxA Uptake System in the Pathogenic Yersinia enterocolitica

  摘要：

  A series of ferrioxamine 6 analogues that target the bacterium Yersinia enterocolitica were prepared. These iron carriers are composed of three hydroxamate-containing monomeric units. Two identical monomers consist of N-hydroxy-3-aminopropionic acid coupled with beta-alanine, and a third unit at the amino terminal is composed of N-hydroxy-3-aminopropionic acid and one of the following amino acids: beta-alanine (1a), phenylalanine (1b), cyclohexylalanine (1c), or glycine (1d). Thermodynamic results for representatives of the analogues have shown a strong destabilization (3-4 orders of magnitude) of the ferric complexes with respect to ferrioxamine B, probably due to shorter spacers and a more strained structure around the metal center. No significant effect of the variations at the N-terminal has been observed on the stability of the ferric complexes. By contrast, using in vivo radioactive uptake experiments, we have found that these modifications have a substantial effect on the mechanism of iron(Ill) uptake in the pathogenic bacteria Yersinia enterocolitica. Analogues la and 1d were utilized by the ferrioxamine B uptake system (FoxA), while 1b and 1c either used different uptake systems or were transported to the microbial cell nonspecifically by diffusion via the cell membrane. Transport via the FoxA system was also confirmed by uptake experiments with the FoxA deficient strain of Yersinia enterocolitica. A fluorescent marker, attached to 1a in a way that did not interfere with its biological activity, provided additional means to monitor the uptake mechanism by fluorescence techniques. Of particular interest is the observation that 1a was utilized by the uptake system of ferrioxamine B in Yersinia enterocolitica (FoxA) but failed to use the ferrioxamine uptake route in Pseudomonas putida. Here, we present a case in which biomimetic siderophore analogues deliberately designed for a particular bacterium can distinguish between related uptake systems of different microorganisms.

  DOI：

  10.1021/ja035182m
• 作为产物：
  描述：

  苄氧基胺盐酸盐 、 丙烯酸乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以10.94 g的产率得到ethyl 3-((benzyloxy)amino)propanoate
  参考文献：
  名称：

  HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE

  摘要：

  揭示了具有以下公式的化合物：其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法，包括用作BMP1、TLL1和/或TLL2的抑制剂以及用于治疗与BMP1、TLL1和/或TLL2活性相关的疾病。

  公开号：

  US20160340328A1

文献信息

• Synthesis and Evaluation of Iron Chelators with Masked Hydrophilic Moieties
  作者：Michael M. Meijler、Rina Arad-Yellin、Z. Ioav Cabantchik、Abraham Shanzer

  DOI：10.1021/ja027013s

  日期：2002.10.1

  Synthetic iron chelators based on the natural siderophore ferrichrome have previously been shown to bind Fe(III) with high affinity (pKf > 27) and have shown no toxicity to mammalian cell cultures in vitro. A new class of lipophilic ferrichrome analogues carrying acetoxymethyl ester moieties has been synthesized. We have shown that these molecules penetrate rapidly through cell membranes and turn highly

  基于天然铁载体铁色素的合成铁螯合剂先前已被证明以高亲和力 (pKf > 27) 结合 Fe(III)，并且在体外对哺乳动物细胞培养物没有显示出毒性。已经合成了一类新的带有乙酰氧基甲基酯部分的亲脂性铁色素类似物。我们已经表明，这些分子在酯酶介导的亲脂性末端水解后，会迅速穿透细胞膜并在细胞内变得高度亲水。通过用荧光萘二亚胺探针标记这些类似物，使细胞内滞留可视化。亲亲水性铁螯合剂已被证明可以高效抑制金属催化的细胞内活性氧的形成，初步结果表明这些分子是有效的抗疟剂。
• [EN] HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE<br/>[FR] DÉRIVÉS D'HYDROXY FORMAMIDE ET LEUR UTILISATION
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2015104684A1

  公开（公告）日：2015-07-16

  Disclosed are compounds having the formula (I): wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.

  揭示了具有以下化学式（I）的化合物：其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法，包括用作BMP1、TLL1和/或TLL2的抑制剂以及用于治疗与BMP1、TLL1和/或TLL2活性相关的疾病。
• HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED

  公开号：US20160340328A1

  公开（公告）日：2016-11-24

  Disclosed are compounds having the formula: wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.

  揭示了具有以下公式的化合物：其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法，包括用作BMP1、TLL1和/或TLL2的抑制剂以及用于治疗与BMP1、TLL1和/或TLL2活性相关的疾病。
• A Molecular Keypad Lock:  A Photochemical Device Capable of Authorizing Password Entries
  作者：David Margulies、Clifford E. Felder、Galina Melman、Abraham Shanzer

  DOI：10.1021/ja065317z

  日期：2007.1.1

  protected at the molecular scale. By harnessing the principles of molecular Boolean logic, we have designed a molecular device that mimics the operation of an electronic keypad lock, e.g., a common security circuit used for numerous applications, in which access to an object or data is to be restricted to a limited number of persons. What distinguishes this lock from a simple molecular logic gate is the

  本文描述了在分子尺度上保护信息的新概念。通过利用分子布尔逻辑的原理，我们设计了一种模拟电子键盘锁操作的分子装置，例如，用于多种应用的通用安全电路，其中对对象或数据的访问仅限于人数有限。这种锁与简单分子逻辑门的区别在于，它的输出信号不仅取决于输入的正确组合，还取决于引入这些输入的正确顺序。换句话说，人们需要知道打开这把锁的确切密码。不同的密码输入由两种化学和一种光学输入信号的组合编码，可以分别激活，芘或荧光素荧光团的蓝色或绿色荧光输出通道。每个通道中的信息是一个单比特光输出信号，可用于授权用户、验证产品的身份验证或启动更高的过程。这一发展不仅为一类新的分子决策设备开辟了道路，而且还为现有的防御技术（如密码学和隐写术）增加了新的保护维度，这些技术以前是用分子实现的。
• Chemical Determinants of antimalarial activity of reversed siderophores
  作者：A Tsafack、J Libman、A Shanzer、Z I Cabantchik

  DOI：10.1128/aac.40.9.2160

  日期：1996.9

  siderophores (RSFs) are artificial hydroxamate-based iron chelators designed after the natural siderophore ferrichrome. The modular molecular design of RSF derivatives allowed the synthesis of various congeners with controlled iron-binding capacities and partition coefficients. These two physicochemical properties were assessed by a novel fluorescent method and were found to be the major determinants of

  反向铁载体（RSF）是基于天然铁载体铁铬酸盐设计的基于人工异羟肟酸酯的铁螯合剂。RSF衍生物的模块化分子设计允许合成具有受控铁结合能力和分配系数的各种同类物。这两种理化性质通过新颖的荧光方法进行了评估，被发现是RSF跨红细胞膜渗透和清除铁离子的主要决定因素。分配系数显然赋予了RSF两个主要特征：（i）在所有发育阶段都能快速进入体外生长的恶性疟原虫铁库的能力，以及动员细胞内铁并将其转移到培养基中的能力；以及（ii）在所有发育阶段抑制寄生虫生长。通过定量确定生物活性的结构-活性关系和跨越广泛值范围的分配系数，可以评估RSF的这些特征。在48小时的测试中，最有效的包含苯丙氨酸芳香基团的RSF（RSFm2phe）的50％抑制浓度为0.60 +/- 0.03 nmol / ml，在5 nmol / ml的抑制环形成作用开始2小时。亲脂性化合物RSFm2phe和亲脂性和酯酶可裂解化合物RSFm2pee