methyl 4-[(4-amino-3-isobutoxybenzoyl)amino]-3-isobutoxybenzoate | 1318208-97-7

• 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: methyl 4-[(4-amino-3-isobutoxybenzoyl)amino]-3-isobutoxybenzoate
• 英文别名: Methyl 4-(4-amino-3-isobutoxybenzamido)-3-isobutoxybenzoate；methyl 4-[[4-amino-3-(2-methylpropoxy)benzoyl]amino]-3-(2-methylpropoxy)benzoate
• CAS: 1318208-97-7
• 化学式: C₂₃H₃₀N₂O₅
• 分子量: 414.502
• InChiKey: ZTTJKHSMYIMGCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-[(4-amino-3-isobutoxybenzoyl)amino]-3-isobutoxybenzoate 在 palladium on activated charcoal 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 Methyl 4-[[4-[[4-amino-3-(2-methylpropoxy)benzoyl]amino]-3-(2-methylpropoxy)benzoyl]amino]-3-(2-methylpropoxy)benzoate
  参考文献：
  名称：

  基于寡酰胺的双α-螺旋模拟物的设计与合成

  摘要：

  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。

  DOI：

  10.1002/ejoc.201300363
• 作为产物：
  描述：

  3-羟基-4-硝基苯甲酸甲酯 在 10% palladium on activated charcoal 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 48.25h， 生成 methyl 4-[(4-amino-3-isobutoxybenzoyl)amino]-3-isobutoxybenzoate
  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

• A Structure—Activity Relationship Study of Bis-Benzamides as Inhibitors of Androgen Receptor—Coactivator Interaction
  作者：Tae-Kyung Lee、Preethi Ravindranathan、Rajni Sonavane、Ganesh V. Raj、Jung-Mo Ahn

  DOI：10.3390/molecules24152783

  日期：——

  chains. A structure–activity relationship study showed that the nitro group at the N-terminus of the bis-benzamide is essential for its biological activity while the C-terminus can have either a methyl ester or a primary carboxamide. Surveying the side chains with various alkyl groups led to the identification of a potent compound 14d that exhibited antiproliferative activity (IC50 value of 16 nM) on PCa

  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，
• MITHRAMYCIN OXIME AND HYDRAZINE DERIVATIVES HAVING INCREASED SELECTIVITY AND ANTI-CANCER ACTIVITY
  申请人：University of Kentucky Research Foundation

  公开号：US20200131218A1

  公开（公告）日：2020-04-30

  Compounds described herein are mithramycin (MTM) oxide (OX) derivatives and MTM Hydrazine (HY) derivatives. These compounds are useful for treatment of cancers and neuro-diseases.

  本文描述的化合物是米司雷霉素（MTM）氧化物（OX）衍生物和MTM肼（HY）衍生物。这些化合物对于治疗癌症和神经疾病非常有用。
• 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。
• Hydrophobic side-chain interactions in a family of dimeric amide foldamers-potential alpha-helix mimetics
  作者：Oleg V. Kulikov、Christopher Incarvito、Andrew D. Hamilton

  DOI：10.1016/j.tetlet.2011.05.004

  日期：2011.7

  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.