tert-butyl (2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)carbamate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl (2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)carbamate
• 英文别名: tert-butyl N-[2-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]ethyl]carbamate
• 化学式: C₁₃H₂₀N₂O₅
• 分子量: 284.312
• InChiKey: PWBFYBSFAHCOLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)carbamate 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以93%的产率得到3-((2-aminoethyl)amino)-4-ethoxycyclobut-3-ene-1,2-dione hydrochloride salt
  参考文献：
  名称：

  研究用于抑制人 SIRT5 赖氨酸脱酰基酶的羧酸等排体和前药**

  摘要：

  一项基于机制的 sirtuin 5 (SIRT5) 水解酶抑制剂的 SAR 研究，包含必需羧酸部分的等排体，为杂环提供了优异的效力和对酶的缓慢、紧密结合的动力学。对细胞中选定化合物的评估表明，杂环的瞬时掩蔽提供了改进的抑制剂，在培养的细胞中具有高水平的靶标参与。

  DOI：

  10.1002/anie.202115805
• 作为产物：
  描述：

  二碳酸二叔丁酯 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 tert-butyl (2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)carbamate
  参考文献：
  名称：

  A 3-Amino-4-hydroxy-3-cyclobutene-1,2-dione-Containing Glutamate Analog Exhibiting High Affinity to Excitatory Amino Acid Receptors

  摘要：

  The syntheses of several novel N-(hydroxydioxocyclobutenyl)-containing analogues of gamma-aminobutyric acid and L-glutamate were undertaken to test the hypothesis that derivatives of 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid), such as 3-amino-4-hydroxy-3-cyclobutene-1,2-dione, could serve as a replacement for the carboxylate moiety in neurochemically interesting molecules. The syntheses were successfully accomplished by preparation of a suitably protected diamine or diamino acid followed by reaction with diethyl squarate. Subsequent deprotection resulted in the isolation of the corresponding N-(hydroxydioxocyclobutenyl)-containing analogues 13, 14, and 18. These analogues were screened as displacers in various neurochemical binding site assays. The L-glutamate analogue 18, which showed high affinity as a displacer for kainate and AMPA binding, was also examined for agonist potency for CA1 pyramidal neurons of the rat hippocampal slice preparation. It rivaled AMPA as one of the most potent agonists for depolarizing pyramidal neurons in medium containing 2.4 mM Mg+2 ions in which kainate/AMPA receptors are active but NMDA receptors are inhibited (IC50 = 1.1 mu M). It was 1 order of magnitude less potent for depolarizing pyramidal neurons under conditions in which kainate/AMPA receptors were inhibited by 10 mu M CNQX but NMDA receptors were active in 0.1 mM Mg+2-containing medium (IC50 = 10 mu M). Compound 18 did not induce sensitization of CA1 pyramidal cells to depolarization by phosphonate analogues of glutamate (the QUIS-effect).

  DOI：

  10.1021/jm00022a007

文献信息

• Introducing a squaramide-based self-immolative spacer for controlled drug release
  作者：Marta Ximenis、Angel Sampedro、Luis Martínez-Crespo、Guillem Ramis、Francisca Orvay、Antonio Costa、Carmen Rotger

  DOI：10.1039/d0cc07683j

  日期：——

  Herein we report the design, synthesis and assessment of the first example of a squaramide-based self-immolative system triggered by an enzymatic reduction. We have proved that the release of the alkylating agent N′,N′-(bis(2-chloroethyl)benzene)-1,4-diamine (ANM) provokes a dramatic reduction of the survival factor in glioblastoma cells, evidencing the suitability of the squaramide-based spacer for drug

  本文中，我们报告了由酶促还原反应引发的基于方胺的自燃系统的第一个实例的设计，合成和评估。我们已经证明，烷基化剂N ′，N ′ -（双（2-氯乙基）苯）-1,4-二胺（ANM）的释放引起胶质母细胞瘤细胞中生存因子的显着降低，证明了其适用性。基于方胺的间隔基，用于药物输送应用。
• Hydrogen Bonded Squaramide-Based Foldable Module Induces Both β- and α-Turns in Hairpin Structures of α-Peptides in Water
  作者：Luís Martínez、Gabriel Martorell、Ángel Sampedro、Pablo Ballester、Antoni Costa、Carmen Rotger

  DOI：10.1021/acs.orglett.5b01268

  日期：2015.6.19

  A novel tertiary squaramido-based reverse-turn module SQ is reported, and its conformational properties are evaluated. This module is easily incorporated into a alpha-peptide sequence by conventional solid-phase peptide synthesis. The structure characterization of the hybrid squaramido-peptide 4 is described, showing that the turn segment induces the formation of hairpin structures in water through the formation of both alpha SQ- and beta SQ-turns.
• [EN] CONJUGATES OF CHEMOTHERAPY AGENTS AND TISSUE-BINDING SMALL MOLECULES, COMPOSITIONS AND METHODS THEREOF<br/>[FR] CONJUGUÉS D'AGENTS DE CHIMIOTHÉRAPIE ET DE PETITES MOLÉCULES DE FIXATION TISSULAIRE, COMPOSITIONS ET MÉTHODES ASSOCIÉES
  申请人：[en]CANWELL BIOTECH LIMITED

  公开号：WO2023151513A1

  公开（公告）日：2023-08-17

  The invention provides novel conjugates of tissue-binding small molecules and therapeutic agents and pharmaceutical compositions thereof, and their use in and methods of treatment of certain diseases or conditions (e.g., cancer).