2-(4-methoxyphenyl)-N-(phenylsulfonyl)acetamide | 1253593-78-0

• 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-(4-methoxyphenyl)-N-(phenylsulfonyl)acetamide
• 英文别名: N-(phenylsulfonyl)-2-(4-methoxyphenyl)acetamide；N-(benzenesulfonyl)-2-(4-methoxyphenyl)acetamide
• CAS: 1253593-78-0
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: PQQWXVQKTIBKQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯磺酰胺 、 对甲氧基苯乙酸 在 aluminum oxide 、 三聚氯氰 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以65%的产率得到2-(4-methoxyphenyl)-N-(phenylsulfonyl)acetamide
  参考文献：
  名称：

  Highly Efficient One-Pot Synthesis of N-Acylsulfonamides Using Cyanuric Chloride at Room Temperature

  摘要：

  本文描述了一种使用氰尿酰氯的高效且温和的一锅法合成N-酰基磺酰胺的方法。在这种合成方法中，结构多样的羧酸和磺胺在氰尿酰氯、三乙胺和氧化铝的存在下，于室温下在无水乙腈中反应，得到了产率极高的各种N-酰基磺酰胺。

  DOI：

  10.1055/s-0029-1218819

文献信息

• Benzyl anion transfer in the fragmentation of N-(phenylsulfonyl)-benzeneacetamides: a gas-phase intramolecular S_NAr reaction
  作者：Shanshan Shen、Yunfeng Chai、Yaqin Liu、Chang Li、Yuanjiang Pan

  DOI：10.1039/c5ob01582k

  日期：——

  substitution (SNAr) during the course of tandem mass spectrometry of deprotonated N-(phenylsulfonyl)-benzeneacetamide. Upon collisional activation, the formation of the initial ion/neutral complex ([C6H5CH2−/C6H5SO2NCO]), which was generated by heterolytic cleavage of the CH2–CO bond, is proposed as the key step. Subsequently, the anionic counterpart, benzyl anion, is transferred to conduct the intra-complex

  在这项研究中，我们报告了在去质子化的N-（苯基磺酰基）-苯乙酰胺串联质谱过程中通过分子内芳香族亲核取代（S N Ar）气相气相苄基阴离子转移。一旦碰撞活化，初始离子的形成中性络合物（[C / 6 ħ 5 CH 2 - / C 6 H ^ 5 SO 2 NCO]），这是由CH的异裂产生的2 -CO键，被提议作为关键步骤。随后，将阴离子对应物苄基阴离子转移以进行内络合物S NAr反应。失去中性HNCO后，该中间体在m / z 231处产生产物离子B，通过比较多级光谱与去质子化的2-苄基苯亚磺酸和（苄基磺酰基）苯的谱图确认了其结构。此外，帧内复杂质子转移也是复杂的[C内观察到6 ħ 5 CH 2 - / C 6 H ^ 5 SO 2 NCO]以产生产物离子Ç在米/ Ž 182. INC介导的机制被证实理论计算，同位素实验，击穿曲线，取代基实验，等。这项工作可以进一步了解气态苄基阴离子的理化性质。
• Metronidazole acid acyl sulfonamide: A novel class of anticancer agents and potential EGFR tyrosine kinase inhibitors
  作者：Yin Luo、Yao Li、Ke-Ming Qiu、Xiang Lu、Jie Fu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.08.038

  日期：2011.10

  A series of novel metronidazole derivatives were recently reported as potent anticancer agents targeting EGFR and HER-2 by our group [Qian, Y.; Zhang, H. J.; Zhang, H.; Xu, C.; Zhao, J.; Zhu, H. L Bioorg. Med. Chem. 2010, 18, 4991]. Based on the previous results, we designed and synthesized a new series of metronidazole acid acyl sulfonamide derivatives and a new series of phenylacetyl benzenesulfonamide derivatives and their anticancer activities were evaluated as potential EGFR and HER-2 kinase inhibitors. Among all the compounds, compound 12 displayed the most potent inhibitory activity EGFR and HER-2 (IC(50) = 0.39 mu M for EGFR and IC(50) = 1.53 mu M for HER-2) and it also showed the most potent growth inhibitory activity against A549 and B16-F10 cancer cell line in vitro, with an IC(50) value of 1.26 mu g/mL for A549 and 0.35 mu g/mL for B16-F10. Docking simulation was further performed to position compound 12 into the EGFR active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly Efficient One-Pot Synthesis of N-Acylsulfonamides Using Cyanuric Chloride at Room Temperature
  作者：Mohammad Soltani Rad、Ali Khalafi-Nezhad、Zeinab Asrari、Somayeh Behrouz

  DOI：10.1055/s-0029-1218819

  日期：2010.8

  A highly efficient and very mild one-pot synthesis of N-acylsulfonamides is described using cyanuric chloride. In this synthesis, structurally diverse carboxylic acids and sulfonamides are reacted in the presence of cyanuric chloride, triethylamine, and alumina in anhydrous acetonitrile at room temperature to afford various N-acylsulfonamides in excellent yields.

  本文描述了一种使用氰尿酰氯的高效且温和的一锅法合成N-酰基磺酰胺的方法。在这种合成方法中，结构多样的羧酸和磺胺在氰尿酰氯、三乙胺和氧化铝的存在下，于室温下在无水乙腈中反应，得到了产率极高的各种N-酰基磺酰胺。