2-amino-N-(3,4,5-trimethoxyphenyl)benzamide | 20878-51-7

• 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: 2-amino-N-(3,4,5-trimethoxyphenyl)benzamide
• CAS: 20878-51-7
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: AFBDOTKADSTOEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-amino-N-(3,4,5-trimethoxyphenyl)benzamide 生成 2-(3,4,5-Trimethoxy-anilinomethyl)-anilin
  参考文献：
  名称：

  3，4-二氢-2（1H）-喹唑啉酮。

  摘要：

  DOI：

  10.1021/jm00312a022
• 作为产物：
  描述：

  2-nitro-N-(3,4,5-trimethoxyphenyl)benzamide 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 2-amino-N-(3,4,5-trimethoxyphenyl)benzamide
  参考文献：
  名称：

  3-(2′-Bromopropionylamino)-benzamides as novel S-phase arrest agents

  摘要：

  We report the synthesis, anti proliferative activity, and SAR of novel 3-(2'-bromopropionylamino)-benzamides. Many of the benzamide compounds showed potent cytotoxicities against Molt-3 leukemia cells. Several compounds exihibited cytotoxicities (under 6.5 mu M) against five solid tumor cell lines. The mechanism of action of the most potent benzamide 101 does not involve targeting on tubulin but it causes cell cycle S-phase arrest. This active S-phase arrest agent merits further investigation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.016

文献信息

• Synthesis, Anti-microbial and Molecular Docking Studies of Quinazolin-4(3H)-one Derivatives
  作者：Yahia Mabkhot、Munirah Al-Har、Assem Barakat、Fahad Aldawsari、Ali Aldalbahi、Zaheer Ul-Haq

  DOI：10.3390/molecules19078725

  日期：——

  In this work, synthesis, antimicrobial activities and molecular docking studies of some new series of substituted quinazolinone 2a–h and 3a–d were described. Starting form 2-aminobenzamide derivatives 1, a new series of quinazolinone derivatives has been synthesized, in high yields, assisted by microwave and classical methods. Some of these substituted quinazolinones were tested for their antimicrobial activity against Gram-negative bacteria (Pseudomonas aeruginosa and Esherichia coli) and Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), and anti-fungal activity against (Aspergillus fumigatus, Saccharomyces cervevisiae, and Candida albicans) using agar well diffusion method. Among the prepared products, 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one (3a) was found to exhibits the most potent in vitro anti-microbial activity with MICs of 25.6 ± 0.5, 24.3 ± 0.4, 30.1 ± 0.6, and 25.1 ± 0.5 µg/mL against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Esherichia coli, respectively. Compound 3a was found to exhibits the most potent in vitro anti-fungal activity with MICs of 18.3 ± 0.6, 23.1 ± 0.4, and 26.1 ± 0. 5 µg/mL against Aspergillus fumigatus, Saccharomyces cervevisiae, and Candidaal bicans, respectively.

  在这项工作中，描述了一些新的取代喹唑啉酮2a–h和3a–d的合成、抗微生物活性及分子对接研究。从2-氨基苯甲酰胺衍生物1出发，通过微波辅助和经典方法，高效合成了一系列喹唑啉酮衍生物。其中一些取代喹唑啉酮通过琼脂孔扩散法测试了它们对革兰氏阴性菌（铜绿假单胞菌和大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）以及抗真菌活性（烟曲霉、酿酒酵母和白色念珠菌）的抗微生物活性。在制备的产品中，3-苄基-2-(4-氯苯基)喹唑啉-4(3H)-酮（3a）表现出最强的体外抗微生物活性，对金黄色葡萄球菌、枯草芽孢杆菌、铜绿假单胞菌和大肠杆菌的MIC值分别为25.6 ± 0.5、24.3 ± 0.4、30.1 ± 0.6和25.1 ± 0.5 µg/mL。化合物3a还表现出最强的体外抗真菌活性，对烟曲霉、酿酒酵母和白色念珠菌的MIC值分别为18.3 ± 0.6、23.1 ± 0.4和26.1 ± 0.5 µg/mL。
• Extending the Structure–Activity Relationship of Anthranilic Acid Derivatives As Farnesoid X Receptor Modulators: Development of a Highly Potent Partial Farnesoid X Receptor Agonist
  作者：Daniel Merk、Christina Lamers、Khalil Ahmad、Roberto Carrasco Gomez、Gisbert Schneider、Dieter Steinhilber、Manfred Schubert-Zsilavecz

  DOI：10.1021/jm500937v

  日期：2014.10.9

  The ligand activated transcription factor nuclear farnesoid X receptor (FXR) is involved as a regulator in many metabolic pathways including bile acid and glucose homeostasis. Therefore, pharmacological activation of FXR seems a valuable therapeutic approach for several conditions including metabolic diseases linked to insulin resistance, liver disorders such as primary biliary cirrhosis or nonalcoholic

  配体激活的转录因子核法呢素X受体（FXR）作为调节剂参与了许多代谢途径，包括胆汁酸和葡萄糖稳态。因此，对于多种疾病，包括与胰岛素抵抗相关的代谢性疾病，肝脏疾病（如原发性胆汁性肝硬化或非酒精性脂肪性肝炎）和某些形式的癌症，FXR的药理激活似乎是一种有价值的治疗方法。但是，可用的FXR激动剂会完全激活受体，这在较长的时间段内可能是不利的。因此，长期治疗代谢紊乱需要部分FXR激活剂。我们在这里报告了作为FXR调节剂的邻氨基苯甲酸衍生物的SAR以及化合物51的开发，合成和表征，它是一种高效的报告基因部分FXR激动剂，在EC 50值为8±3 nM，在肝细胞中的mRNA水平上。
• Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
  作者：Gopal Chandru Senadi、Vishal Suresh Kudale、Jeh-Jeng Wang

  DOI：10.1039/c8gc03839b

  日期：——

  identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone

  首次将TsOH·H 2 O / O 2和适当的双亲核试剂组合使用，将醇和醚确定为可持续的次甲基来源，用于合成喹唑啉酮和苯并咪唑衍生物。氘标记研究清楚地证明了合成杂环的C 2氢来自次甲基。这些独特的反应条件已成功地用于合成棘金龙酮（2e'），2f'（rutaecarpine和（±）evodiamine的常见前体）和二咪唑（6d）。该方法的显着特征包括低毒性，使用商业原料作为底物，成本低，对官能团的耐受性强以及对多种双亲核起始原料的适用性。
• A robust synthesis of functionalized 2 H -indazoles via solid state melt reaction (SSMR) and their anti-tubercular activity
  作者：Shinde Vidyacharan、Chandan Adhikari、Vagolu Siva Krishna、Rudraraju Srilakshmi Reshma、Dharmarajan Sriram、Duddu S. Sharada

  DOI：10.1016/j.bmcl.2017.02.021

  日期：2017.4

  screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, compound 3u (MIC: 4.20μM) was found to be most active and are superior over existing standard drugs ciprofloxacin and ethambutol. Compounds 3c and 3x were found to equally potent as ethambutol. Among most potent compounds in the series, four compounds (3n, 3o, 3p and 3u) showed lower cytotoxicity which could be promising

  已经开发了一种简便易行的方法，用于在无催化剂条件下使用容易获得的起始原料通过固态熔融反应合成官能化的吲唑。该转变涉及经由在热条件下获得的共轭腈中间体进行电环化。在针对结核分枝杆菌H37Rv的体外分枝杆菌活性筛选的化合物3a-3x中，对分子进行了进一步的抗结核活性筛选，发现化合物3u（MIC：4.20μM）活性最高，并且优于现有的标准药物环丙沙星和乙胺丁醇。发现化合物3c和3x与乙胺丁醇同样有效。在该系列中最有效的化合物中，有四个化合物（3n，3o，
• Natural surfactant mediated phytosynthesis and solvatochromic fluorescence of 2-aminobenzamide derivatives
  作者：Pallavi More、Amol Patil、Rajashri Salunkhe

  DOI：10.1039/c4ra09514f

  日期：——

  A green synthesis and intriguing solvatochromic behaviour of 2-aminobenzamide derivatives in varying solvents has been investigated. The biomaterial in the form of an aqueous extract of mesocarp of the fruit of the Balanites roxburghii plant as a natural surfactant reaction medium has been employed for phytosynthesis with quantitative yield at 60 °C. The reaction proceeds effortlessly in a short reaction time with easy product formation. The fluorescence property of some synthesized compounds was studied, along with the interesting solvatochromic behaviour of 2-amino-N-benzylbenzamide.

  对2-氨基苯甲酰胺衍生物在不同溶剂中的绿色合成和有趣的溶剂化变色行为进行了研究。采用Balanites roxburghii植物果肉水提物作为天然表面活性剂反应介质，在60°C下进行植物合成，产率定量。反应在短时间内无需费力进行，产物易于形成。研究了某些合成化合物的荧光性质，以及2-氨基-N-苄基苯甲酰胺的溶剂化变色行为。