2-hydroxy-N-(4-methoxyphenyl)nicotinamide | 81685-46-3

• 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-(4-methoxyphenyl)nicotinamide
• 英文别名: N-(4-methoxyphenyl)-2-oxo-1H-pyridine-3-carboxamide
• CAS: 81685-46-3
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: UMKHBSUOIXDMBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基烟酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-hydroxy-N-(4-methoxyphenyl)nicotinamide
  参考文献：
  名称：

  Cativiela, C; Fernandez, J.; Melendez, E., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1093 - 1097

  摘要：

  DOI：

文献信息

• 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。
• 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.
• CATIVIELA, C.;FERNANDEZ, J.;MELENDEZ, E., J. HETEROCYCL. CHEM., 1982, 19, N 5, 1093-1097
  作者：CATIVIELA, C.、FERNANDEZ, J.、MELENDEZ, E.

  DOI：——

  日期：——