N-[5-(4-甲氧基苯基)吡啶-2-基]苯甲酰胺 | 1044239-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: N-[5-(4-甲氧基苯基)吡啶-2-基]苯甲酰胺
• 英文名称: N-(5-(4-methoxyphenyl)pyridin-2-yl)benzamide
• 英文别名: N-[5-(4-Methoxyphenyl)pyridin-2-yl]benzamide
• CAS: 1044239-24-8
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: DTZTUPNDUJOKPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(4-methoxyphenyl)-2-phenylimidazo[1,2-a]pyridine 在 高氯酸 、 lithium perchlorate 作用下， 以 二甲基亚砜 为溶剂， 以59 %的产率得到N-[5-(4-甲氧基苯基)吡啶-2-基]苯甲酰胺
  参考文献：
  名称：

  Easy Access to N-(Pyridin-2-yl)benzamides through Electro-oxidative Ring Opening of 2-Arylimidazo[1,2-a]pyridines

  摘要：

  摘要 报告了一种用于咪唑吡啶衍生物开环的电氧化方法。这种温和的方法为现有的苛刻反应条件提供了一种可持续的替代方案，并为生产对不同官能团具有良好耐受性的 N-(吡啶-2-基)酰胺衍生物提供了一种有效的方法。系统的机理研究深入揭示了反应途径，并发现 DMSO 的残余水是产物中氧原子的来源。

  DOI：

  10.1055/a-1956-9993

文献信息

• False Positives in a Reporter Gene Assay: Identification and Synthesis of Substituted <i>N</i>-Pyridin-2-ylbenzamides as Competitive Inhibitors of Firefly Luciferase
  作者：Laura H. Heitman、Jacobus P. D. van Veldhoven、Annelien M. Zweemer、Kai Ye、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm8004509

  日期：2008.8.1

  Luciferase reporter-gene assays are a commonly used technique in high-throughput screening campaigns. In this study, we report on a luciferase inhibitor (1), which emerged from an antagonistic G protein-coupled receptor luciferase reporter-gene assay screen. Instead of displaying receptor activity, compound I was shown to potently inhibit luciferase in an in vitro enzymatic assay with an IC50 value of 1.7 +/- 0.1 mu M. In addition, 1 was a competitive inhibitor with respect to the substrate luciferin. A database search yielded another inhibitor (3) with a similar N-pyridin-2-ylbenzamide core. Subsequently, several analogues were prepared to investigate the structure-activity relationships of these luciferase inhibitors. This yielded the most potent inhibitor of this series (6) with an IC50 value of 0.069 +/- 0.01 mu M. Further molecular modeling studies suggested that 6 can be accommodated in the luciferin binding site. This paper is meant to alert users of luciferase reporter-gene assays for possible false positive hits including highly "druglike" molecules due to direct luciferase inhibition.
• Easy Access to N-(Pyridin-2-yl)benzamides through Electro-oxidative Ring Opening of 2-Arylimidazo[1,2-a]pyridines
  作者：Sayan Ghosh、Jhilik Dutta、Suman De Sarkar、Atreyee Halder

  DOI：10.1055/a-1956-9993

  日期：——

  An electro-oxidative method for the ring opening of imidazopyridine derivatives is reported. This mild protocol offers a sustainable alternative to the existing harsh reaction conditions and unleashes an efficient approach to produce N-(pyridin-2-yl)amide derivatives with good tolerance of different functional groups. Systematic mechanistic studies provided insight into the reaction pathway and revealed that the residual water of DMSO is the source of oxygen atoms in the products.

  摘要 报告了一种用于咪唑吡啶衍生物开环的电氧化方法。这种温和的方法为现有的苛刻反应条件提供了一种可持续的替代方案，并为生产对不同官能团具有良好耐受性的 N-(吡啶-2-基)酰胺衍生物提供了一种有效的方法。系统的机理研究深入揭示了反应途径，并发现 DMSO 的残余水是产物中氧原子的来源。