3,4,5-trimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide | 199584-07-1

• 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: 3,4,5-trimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide
• 英文别名: [N-(4-methoxy-2-nitrophenyl)]-3,4,5-trimethoxybenzylamide；N-(2-Nitro-4-methoxyphenyl)(3,4,5-trimethoxybenzamide)
• CAS: 199584-07-1
• 化学式: C₁₇H₁₈N₂O₇
• 分子量: 362.339
• InChiKey: CVHKFMZCEACBLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide 在 氢气 、 钯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.5h， 生成 N-{2-[(2,2-dimethylpropanoyl)amino]-4-methoxyphenyl}-3,4,5-trimethoxybenzamide
  参考文献：
  名称：

  A journey from benzanilides to dithiobenzanilides: Synthesis of selective spasmolytic compounds

  摘要：

  A series of dithiobenzanilide derivatives was synthesized and each compound was evaluated for its ability to reduce KCl-induced contractions of smooth muscle preparations of the guinea pig. Starting from a recent publication describing benzanilide derivatives as antispasmodic agents, structure-activity guided synthesis was performed to obtain compounds with improved spasmolytic activity. First, compounds with two amide bonds were designed and second, both amide oxygens were replaced by two sp(2) sulfur atoms resulting in dithiobenzanilide derivatives. The most potent antispasmodic dithiobenzanilide 19 showed improved activity with an IC50 value of 0.4 mu M. Moreover, the study also demonstrated that these active compounds were able to antagonize the effect of spasmogens like acetylcholine and phenylephrine and that the activity is not mediated by activation of ATP-dependent potassium channels (K-ATP-channels) or inhibition of endothelial nitric oxide synthase (eNOS). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.043
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰氯 、 2-硝基-4-甲氧基苯胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以49.7%的产率得到3,4,5-trimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide
  参考文献：
  名称：

  氨基取代的苯甲酰胺衍生物作为有望的抗氧化剂：结合实验和计算研究。

  摘要：

  我们制备了一系列具有可变数目的甲氧基和羟基的N-芳基苯甲酰胺，带有氨基或氨基质子化的部分，并使用DPPH和FRAP分析来评估其抗氧化能力。相对于参考BHT分子，大多数系统在两种测定法中均表现出改进的抗氧化性能。结合两组实验的结果，三羟基衍生物26显示出最有前途的抗氧化潜能，我们建议将其作为进一步优化苯甲酰胺支架的先导化合物。计算分析有助于解释观察到的趋势，并证明质子化系统比中性系统更好的抗氧化剂，同时潜在于供电子甲氧基对抗氧化剂性能的积极影响，从而证实了实验。还揭示了羟基的引入将酰胺和胺基的反应性移向该部分，并另外增强了抗氧化特性。这在26H •+中尤为明显，这归因于其稳定的[O •···H–O]产生的苯氧基自由基与两个相邻的羟基之间的氢键。我们证明了它的抗氧化活性比不具有N-苯基或不具有酰胺部分的类似三羟基衍生物的抗氧化活性更好，这有力地证明了在设计有效的抗氧化剂中利用双苯基酰胺所采用的策略是合理的。

  DOI：

  10.1021/acs.chemrestox.8b00175

文献信息

• Method for treating neoplasia by exposure to substituted 2-aryl-benzimidazole derivatives
  申请人：Cell Pathways, Inc.

  公开号：US06211177B1

  公开（公告）日：2001-04-03

  A method for inhibiting neoplasia, particularly cancerous and precancerous lesions, by exposing the affected cells to substituted 2-aryl-benzimidazoles.

  一种通过将受影响的细胞暴露于取代的2-芳基苯并咪唑类化合物来抑制肿瘤，特别是癌症和癌前病变的方法。
• Method for treating neoplasia by exposure to N,N′-substituted benzimidazol-2-ones
  申请人：Cell Pathways, Inc.

  公开号：US06420410B1

  公开（公告）日：2002-07-16

  A method for inhibiting neoplastic cells and related conditions by exposing them to N,N′-substituted benzimidazol-2-ones.

  通过将肿瘤细胞及相关病况暴露于N,N′-取代苯并咪唑-2-酮中来抑制它们的方法。
• Potent Galloyl-Based Selective Modulators Targeting Multidrug Resistance Associated Protein 1 and P-glycoprotein
  作者：Raffaella Zoe Pellicani、Angela Stefanachi、Mauro Niso、Angelo Carotti、Francesco Leonetti、Orazio Nicolotti、Roberto Perrone、Francesco Berardi、Saverio Cellamare、Nicola Antonio Colabufo

  DOI：10.1021/jm201305y

  日期：2012.1.12

  The multifactorial nature of chemotherapy failure in controlling cancer is often associated with the occurrence of multidrug resistance (MDR), a phenomenon likely related to the increased expression of members of the ATP binding cassette (ABC) transporter superfamily. In this respect, the most extensively characterized MDR transporters include ABCB1 (also known as MDR1 or P-glycoprotein) and ABCC1 (also known as MRP1) whose inhibition remains a priority to circumvent drug resistance. Herein, we report how the simple galloyl benzamide scaffold can be easily and properly decorated for the preparation of either MRP1 or P-gp highly selective inhibitors. In particular, some gallamides and pyrogallol-l-monomethyl ethers showed remarkable affinity and selectivity toward MRP1. On the other hand, trimethyl ether galloyl anilides, with few exceptions, exhibited moderate to very high and selective P-gp inhibition.
• Design, synthesis and biological studies of novel tubulin inhibitors
  作者：Yanjun Sun、Bulbul Pandit、Somsundaram N. Chettiar、Jonathan P. Etter、Andrew Lewis、Jayasekar Johnsamuel、Pui-Kai Li

  DOI：10.1016/j.bmcl.2013.04.078

  日期：2013.8

  A series of compounds originally derived from the vascular endothelial growth factor receptor tyrosine kinase inhibitor, SU5416, were synthesized and evaluated. The most potent compound in this series, compound 3, which structurally resembles the potent anti-microtubule agent combretastatin A-4, inhibited tubulin polymerization and showed potent growth inhibitory activities on both prostate and breast cancer lines with IC50 values in the low nanomolar range. (C) 2013 Elsevier Ltd. All rights reserved.
• US6211177B1
  申请人：——

  公开号：US6211177B1

  公开（公告）日：2001-04-03