3-isobutoxy-4-(3-isobutoxy-4-nitrobenzamido)benzoic acid | 1318208-99-9

• 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: 3-isobutoxy-4-(3-isobutoxy-4-nitrobenzamido)benzoic acid
• 英文别名: 3-isobutoxy-4-[(3-isobutoxy-4-nitrobenzoyl)amino]benzoic acid；3-(2-Methylpropoxy)-4-[[3-(2-methylpropoxy)-4-nitrobenzoyl]amino]benzoic acid
• CAS: 1318208-99-9
• 化学式: C₂₂H₂₆N₂O₇
• 分子量: 430.458
• InChiKey: SVTUHQAOSUHFHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-isobutoxy-4-(3-isobutoxy-4-nitrobenzamido)benzoic acid 在 C₂₁H₃₁N₃OP⁽¹⁺⁾ 、 氨 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 N-(2-aminoethyl)-3-isobutoxy-4-(3-isobutoxy-4-nitrobenzamido)benzamide
  参考文献：
  名称：

  双苯甲酰胺作为雄激素受体-共激活剂相互作用抑制剂的结构-活性关系研究

  摘要：

  雄激素受体 (AR) 和共激活蛋白之间的相互作用在 AR 介导的前列腺癌 (PCa) 细胞生长中起着关键作用，因此其抑制作用正在成为一种有前景的 PCa 治疗策略。为了开发 AR-共激活剂相互作用的有效抑制剂，我们通过修饰 N/C 末端和侧链的官能团设计并合成了一系列双苯甲酰胺。构效关系研究表明，双苯甲酰胺 N 端的硝基对其生物活性至关重要，而 C 端可以有甲酯或伯甲酰胺。调查具有各种烷基的侧链导致鉴定出对 PCa 细胞表现出抗增殖活性（IC50 值为 16 nM）的强效化合物 14d。此外，

  DOI：

  10.3390/molecules24152783
• 作为产物：
  描述：

  methyl 3-isobutoxy-4-(3-isobutoxy-4-nitrobenzamido)-benzoate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以46%的产率得到3-isobutoxy-4-(3-isobutoxy-4-nitrobenzamido)benzoic acid
  参考文献：
  名称：

  Hydrophobic side-chain interactions in a family of dimeric amide foldamers-potential alpha-helix mimetics

  摘要：

  A series of new alpha-helix mimetics based on a benzamide scaffold and potentially able to disrupt protein-protein interactions have been synthesized and characterized by X-ray analysis. Inspection of the solid state structures of aromatic amide dimers confirmed that the molecules adopt a curved conformation with intramolecular H-bonding between the amide NH and the alkoxy oxygen of the neighboring aromatic fragment (d(NH center dot center dot center dot O) similar to 2 angstrom). Adjacent dimer molecules are prone to form supramolecular assemblies due to both hydrophobic alkyl side-chain/side-chain interactions and intermolecular H-bonding. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.004

文献信息

• Design and Synthesis of Oligoamide-Based Double α-Helix Mimetics
  作者：Oleg V. Kulikov、Sam Thompson、Hai Xu、Christopher D. Incarvito、Richard T. W. Scott、Ishu Saraogi、Laura Nevola、Andrew D. Hamilton

  DOI：10.1002/ejoc.201300363

  日期：2013.6

  An extensive series of bis-oligobenzamides and bis-oligopyridylamides have been efficiently prepared and studied by X-ray analysis and computational methods. A modular synthesis led to double -helix mimics bearing between two and ten branched side-chains. The inter-helix angle and distance can be tuned by varying the length and rigidity of the spacer, thereby reproducing the recognition domains of

  已经通过 X 射线分析和计算方法有效地制备和研究了一系列广泛的双低聚苯甲酰胺和双低聚吡啶基酰胺。模块化合成导致双螺旋模拟物在两到十个支链侧链之间承载。可以通过改变间隔物的长度和刚度来调整螺旋间角度和距离，从而再现一系列超二级结构的识别域。
• Perturbation of the c-Myc–Max Protein–Protein Interaction via Synthetic α-Helix Mimetics
  作者：Kwan-Young Jung、Huabo Wang、Peter Teriete、Jeremy L. Yap、Lijia Chen、Maryanna E. Lanning、Angela Hu、Lester J. Lambert、Toril Holien、Anders Sundan、Nicholas D. P. Cosford、Edward V. Prochownik、Steven Fletcher

  DOI：10.1021/jm501440q

  日期：2015.4.9

  The rational design of inhibitors of the bHLH-ZIP oncoprotein c-Myc is hampered by a lack of structure in its monomeric state. We describe herein the design of novel, low-molecular-weight, synthetic a-helix mimetics that recognize helical c-Myc in its transcriptionally active coiled-coil structure in association with its obligate bHLH-ZIP partner Max. These compounds perturb the heterodimers binding to its canonical E-box DNA sequence without causing protein-protein dissociation, heralding a new mechanistic class of direct c-Myc inhibitors. In addition to electrophoretic mobility shift assays, this model was corroborated by further biophysical methods, including NMR spectroscopy and surface plasmon resonance. Several compounds demonstrated a 2-fold or greater selectivity for c-Myc-Max heterodimers over Max-Max homodimers with IC50 values as low as 5.6 mu M. Finally, these compounds inhibited the proliferation of c-Myc-expressing cell lines in a concentration-dependent manner that correlated with the loss of expression of a c-Myc-dependent reporter plasmid despite the fact that c-MycMax heterodimers remained intact.
• OLIGO-BENZAMIDE COMPOUNDS AND THEIR USE
  申请人：Ahn Jung-Mo

  公开号：US20130231385A1

  公开（公告）日：2013-09-05

  The present invention includes bis- and tris-benzamide compounds that block AR signaling and have anticancer activity. Uses for these compounds, and pharmaceutical compositions containing the same, also are provided.
• US9856206B2
  申请人：——

  公开号：US9856206B2

  公开（公告）日：2018-01-02
• [EN] OLIGO-BENZAMIDE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS OLIGO-BENZAMIDE ET LEUR UTILISATION
  申请人：UNIV TEXAS

  公开号：WO2011150360A1

  公开（公告）日：2011-12-01

  The present invention includes bis- and tris-benzamide compounds that block AR signaling and have anticancer activity. Uses for these compounds, and pharmaceutical compositions containing the same, also are provided.