2-hydroxy-N-(p-tolyl)nicotinamide | 72646-01-6

• 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-hydroxy-N-(p-tolyl)nicotinamide
• 英文别名: 2-hydroxy-N-p-tolylnicotinamide；1,2-Dihydro-N-(4-methylphenyl)-2-oxo-3-pyridinecarboxamide；N-(4-methylphenyl)-2-oxo-1H-pyridine-3-carboxamide
• CAS: 72646-01-6
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: LHRIIGLRPGBVHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-Methylphenoxy)nicotinamide 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-hydroxy-N-(p-tolyl)nicotinamide
  参考文献：
  名称：

  基于可调节微笑重排的 N-芳基-烟酰胺和二芳基胺的一锅法合成

  摘要：

  一锅 Smiles 重排已被开发为一种有用的协议，用于直接合成不同的 N-芳基-烟酰胺。该方法还提供了基于酰胺基团的不同取代对二芳基胺的化学选择性途径。转化的潜在应用以市售琥珀酸脱氢酶抑制剂啶酰菌胺的合成为例。

  DOI：

  10.1002/ejoc.201500222

文献信息

• ARYLOYL(OXY OR AMINO)PENTAFLUOROSULFANYLBENZENE COMPOUND, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PRODRUGS THEREOF
  申请人：UBE INDUSTRIES, LTD.

  公开号：US20160244407A1

  公开（公告）日：2016-08-25

  An aryloyl(oxy or amino)pentafluorosulfanylbenzene compound having pharmacological action. The aryloyl(oxy or amino)pentafluorosulfanylbenzene compound is represented by general formula (A-I), a pharmaceutically acceptable salt thereof, and a prodrug thereof, wherein all of parameters represent the same meanings as defined in the specification.

  一种具有药理作用的芳基酰氧或氨基五氟磺基苯化合物。该芳基酰氧或氨基五氟磺基苯化合物由通用式(A-I)表示，其药用可接受的盐和前药，其中所有参数的含义与规范中定义的相同。
• Design of novel N-phenylnicotinamides as selective cyclooxygenase-1 inhibitors
  作者：Lei Shi、Zi-Lin Li、Ying Yang、Zhen-Wei Zhu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2010.11.062

  日期：2011.1

  A series of N-phenylnicotinamides (1-40) were designed and evaluated in vitro for their COX inhibitory activities. Most of the synthesized compounds were proved to be potent and selective inhibitors of COX-1. Compound 28 showed the most potent COX-1 inhibitory activity (COX-1 IC50 = 0.68 +/- 0.07 mu M) and good selectivity (COX-2 IC50 > 100 mu M). This compound may be useful as a lead compound for superior COX-1 inhibitors. On the basis of the biological results, structure-activity relationships for the COX-1-inhibitory activities of the synthesized N-phenylnicotinamides were discussed concisely. (C) 2010 Elsevier Ltd. All rights reserved.
• US9682931B2
  申请人：——

  公开号：US9682931B2

  公开（公告）日：2017-06-20
• One-Pot Synthesis of<i>N</i>-Aryl-Nicotinamides and Diarylamines Based on a Tunable Smiles Rearrangement
  作者：Shihui Liu、Shaofan Zhu、Ying Wu、Jiayu Gao、Pengfei Qian、Yanwei Hu、Linsen Shi、Shaohua Chen、Shilei Zhang、Yinan Zhang

  DOI：10.1002/ejoc.201500222

  日期：2015.5

  A one-pot Smiles rearrangement has been developed as a useful protocol for the straightforward synthesis of diverse N-aryl-nicotinamides. This method also provides chemoselective access toward diarylamines based on the different substitutions of the amide group. The potential application of the transformation is exemplified by the synthesis of an on-market succinate dehydrogenase inhibitor, boscalid

  一锅 Smiles 重排已被开发为一种有用的协议，用于直接合成不同的 N-芳基-烟酰胺。该方法还提供了基于酰胺基团的不同取代对二芳基胺的化学选择性途径。转化的潜在应用以市售琥珀酸脱氢酶抑制剂啶酰菌胺的合成为例。