2-([(tert-butoxy)carbonyl]{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)acetic acid | 194996-03-7

• 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: 2-([(tert-butoxy)carbonyl]{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)acetic acid
• 英文别名: N-((tert-butyloxy)carbonyl)-N'-(4-methoxybenzyl)iminodiacetic acid monoamide；N-((t-butyloxy)carbonyl)-N'-(4-methoxybenzyl)iminodiacetic acid monoamide
• CAS: 194996-03-7
• 化学式: C₁₇H₂₄N₂O₆
• 分子量: 352.387
• InChiKey: UTPAMYWMPLNHNO-UHFFFAOYSA-N

物化性质

• 沸点：
  578.0±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-([(tert-butoxy)carbonyl]{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)acetic acid 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Higher order iminodiacetic acid libraries for probing protein–protein interactions

  摘要：

  Full details of the preparation of iminodiacetic acid diamide dimer (2040 compounds), trimer (560 compounds), and tetramer (1596 compounds) libraries by multistep convergent solution-phase synthesis for studying protein-protein interactions are provided. The libraries were assembled in a format providing small 8-10 compound mixtures and the deconvolution of many of the small mixtures to identify screening leads by resynthesis of the individual components have been conducted for 320 of the individual compounds to date. A representative example of the subsequent exploration of the structure-activity relationships for an identified receptor binding antagonist (200 additional individual compounds) and steps taken for potential elaboration to a receptor dimerization agonist are defined with preparation of representative linked dimers (70 compounds). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00128-x
• 作为产物：
  描述：

  N-BOC-亚氨基二乙酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 2-([(tert-butoxy)carbonyl]{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)acetic acid
  参考文献：
  名称：

  非肽缓激肽拮抗剂的溶液相组合合成。

  摘要：

  我们描述了作为非肽B2拮抗剂的五十种N，N（'）-取代-N“ -1-（4-氯苯甲基）哌嗪亚氨基二乙酸三酰胺衍生物的溶液相组合合成和药理作用，并测试了其合成化合物的抗缓激肽作用N-乙酰基-N（'）-（4-甲基苄基）-N“ -1-（4-氯苯甲酰基）哌嗪亚氨基二乙酸三酰胺（A3B1C1）在100nM时显示46％的抑制作用。

  DOI：

  10.1016/j.bmc.2004.04.031

文献信息

• Non-Amide-Based Combinatorial Libraries Derived fromN-Boc-Iminodiacetic Acid: Solution-Phase Synthesis of Piperazinone Libraries with Activity Against LEF-1/β-Catenin-Mediated Transcription
  作者：Dale L. Boger、Joel Goldberg、Shigeki Satoh、Yves Ambroise、Steven B. Cohen、Peter K. Vogt

  DOI：10.1002/1522-2675(20000809)83:8<1825::aid-hlca1825>3.0.co;2-4

  日期：2000.8.9

  methodology was applied to the synthesis of a diverse 150-member library with substituents in three positions of the piperazinone core. Screening results from a luciferase reporter assay indicate that a number of library members are novel repressors of LEF-1/β-catenin-mediated transcription, and may be effective agents against colorectal tumors. Two secondary libraries (100 members each) designed from

  详细介绍了从 N-Boc-亚氨基二乙酸开始仅需四个步骤即可快速、平行合成高度官能化哌嗪酮的溶液相方法。这些努力代表了组合文库的溶液相合成从 N-Boc-亚氨基二乙酸扩展到基于非酰胺的文库，其中使用简单的液-液萃取来纯化所有反应产物。该方法被应用于合成一个多样化的 150 成员库，在哌嗪酮核心的三个位置具有取代基。荧光素酶报告基因检测的筛选结果表明，许多文库成员是 LEF-1/β-连环蛋白介导的转录的新阻遏物，可能是对抗结肠直肠肿瘤的有效药物。合成和筛选了从这些先导结构设计的两个二级库（每个 100 个成员），提供额外的活性剂并深入了解该系列中的关键结构-活性关系。这些化合物仅代表第二类小分子，其抑制含有 LEF-1 响应元件的报告基因的转录，第一类不基于 DNA 小沟结合剂。
• Synthesis and Evaluation of (4-Chlorobenzhydryl) Piperazine Amides as Sodium Channel Nav1.7 Inhibitors
  作者：Seung Keun Back、Yoo Lim Kam、Jung Ae Oh、Heung Sik Na、Uhtaek Ih、Hea-Young Park Choo

  DOI：10.1002/bkcs.10446

  日期：2015.9

  Blockage of voltage‐gated sodium channels is used to treat neuropathic pain which is chronic and can become debilitating. Sodium channels Nav1.7–1.9 are especially attractive targets for drug discovery because of the broad therapeutic potential of their modulation. For a neuropathic pain therapy, anticonvulsant like lamotrigine, carbamazepine and a topical anesthetic such as Lidocaine are used. A growing

  电压门控钠通道的阻塞可用于治疗神经性疼痛，这种慢性疼痛可能会变得虚弱。钠离子通道Nav1.7–1.9特别适合作为药物研发的靶标，因为其调节具有广阔的治疗潜力。对于神经性疼痛疗法，应使用拉莫三嗪，卡马西平等抗惊厥药和利多卡因等局部麻醉药。越来越多的临床报告表明，Nav1.7的选择性抑制剂可能是治疗广泛疼痛状况的有效镇痛药。因此，我们通过VIPR（电压/离子探针阅读器），使用电压传感器荧光染料和稳定的HEK-293细胞系的荧光图像平板阅读器（FLIPR）分析评估了在人Nav1.7（hNav1.7）上合成的108种酰胺衍生物表达hNaV1.7。5和6）的IC 50值为8-10μM。
• Generation of targeted C2-symmetrical compound libraries by solution-phase combinatorial chemistry
  作者：Dale L. Boger、Rachel S. Ozer、Carl-Magnus Andersson

  DOI：10.1016/s0960-894x(97)00330-2

  日期：1997.7

  An approach to the preparation of C-2-symmetrical chemical libraries for use in protein and receptor homodimerization studies by solution-phase methods which permits the multi-milligram synthesis of each member is described. (C) 1997 Elsevier Science Ltd.
• WO2007/108566
  申请人：——

  公开号：——

  公开（公告）日：——
• Higher order iminodiacetic acid libraries for probing protein-protein interactions
  作者：Dale L. Boger、Pierre Ducray、Wenying Chai、Weiqin Jiang、Joel Goldberg

  DOI：10.1016/s0960-894x(98)00423-5

  日期：1998.9

  Higher order iminodiacetic acid diamide trimer (560 compounds) and tetramer libraries (1260 compounds) are described and were assembled in a convergent multistep solution-phase synthesis for use in studying protein-protein interactions. (C) 1998 Elsevier Science Ltd. All rights reserved.