2-(4-(benzyloxy)phenyl)-2-(phenylamino)acetonitrile | 586982-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-(benzyloxy)phenyl)-2-(phenylamino)acetonitrile
• 英文别名: [4-(Benzyloxy)phenyl](phenylamino)acetonitrile；2-anilino-2-(4-phenylmethoxyphenyl)acetonitrile
• CAS: 586982-64-1
• 化学式: C₂₁H₁₈N₂O
• 分子量: 314.387
• InChiKey: PXOWOUCLDMMVHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-(benzyloxy)phenyl)-2-(phenylamino)acetonitrile 在 氧气 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 9.0h， 以74%的产率得到4-benzyloxybenzanilide
  参考文献：
  名称：

  在无金属条件下从 α-氨基腈制备酰胺的 Umpolung 路线

  摘要：

  已经开发了一种无金属、碱介导的 α-氨基腈脱氰，以使用 O 2或空气作为酰胺氧源来合成二级和三级酰胺。自由基清除研究表明，C-CN 键的断裂可以通过阴离子途径进行。该工作的实用性还通过从相应的醛和胺原位生成的 α-氨基腈得到酰胺来证明。这项工作的重要特征包括广泛的官能团相容性、41% 至 89% 的产品产率、2° 和 3° 酰胺的克级合成、广泛的底物范围和 umpolung 策略。

  DOI：

  10.1002/adsc.202200607
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 苯胺 在 碘 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 2-(4-(benzyloxy)phenyl)-2-(phenylamino)acetonitrile
  参考文献：
  名称：

  Identification of small molecule sphingomyelin synthase inhibitors

  摘要：

  Sphingomyelin synthase (SMS), which catalyzes ceramide as one of the substrates to produce sphingomyelin, is a critical factor in the sphingolipid biosynthesis pathway. Recent studies indicated that SMS could serve as a novel potential drug target for the treatment of various metabolic diseases such as insulin resistance and atherosclerosis. However, very few small-molecule inhibitors of SMS are known. In this study, we performed structure-based virtual screening in combination with chemical synthesis and bioassay and discovered a class of small-molecule SMS inhibitors. The most potent compound exhibited an IC50 value lower than 20 mu M in an in vitro enzymatic assay. To the best of our knowledge, this is the first time that small-molecule SMS inhibitors with potency close to the micromolar range are publicly revealed. The structure-activity relationship demonstrated by this class of compounds provides insights into the structural features that are essential for effective SMS inhibition. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.002

文献信息

• Identification of small molecule sphingomyelin synthase inhibitors
  作者：Xiaodong Deng、Fu Lin、Ya Zhang、Yan Li、Lu Zhou、Bin Lou、Yue Li、Jibin Dong、Tingbo Ding、Xiancheng Jiang、Renxiao Wang、Deyong Ye

  DOI：10.1016/j.ejmech.2013.12.002

  日期：2014.2

  Sphingomyelin synthase (SMS), which catalyzes ceramide as one of the substrates to produce sphingomyelin, is a critical factor in the sphingolipid biosynthesis pathway. Recent studies indicated that SMS could serve as a novel potential drug target for the treatment of various metabolic diseases such as insulin resistance and atherosclerosis. However, very few small-molecule inhibitors of SMS are known. In this study, we performed structure-based virtual screening in combination with chemical synthesis and bioassay and discovered a class of small-molecule SMS inhibitors. The most potent compound exhibited an IC50 value lower than 20 mu M in an in vitro enzymatic assay. To the best of our knowledge, this is the first time that small-molecule SMS inhibitors with potency close to the micromolar range are publicly revealed. The structure-activity relationship demonstrated by this class of compounds provides insights into the structural features that are essential for effective SMS inhibition. (C) 2013 Elsevier Masson SAS. All rights reserved.
• An Umpolung Route to Amides from α‐Aminonitriles under Metal‐Free Conditions
  作者：Sathyendran Swetha、Gopal Chandru Senadi

  DOI：10.1002/adsc.202200607

  日期：2022.8.16

  synthesize secondary and tertiary amides using O2 or air as an amide oxygen source. Radical scavenging studies disclosed that the cleavage of C−CN bond may proceed via an anionic pathway. The practicality of the work was also demonstrated through an in situ generated α-aminonitriles from corresponding aldehydes and amines to afford amides. The important features of this work include broad functional group

  已经开发了一种无金属、碱介导的 α-氨基腈脱氰，以使用 O 2或空气作为酰胺氧源来合成二级和三级酰胺。自由基清除研究表明，C-CN 键的断裂可以通过阴离子途径进行。该工作的实用性还通过从相应的醛和胺原位生成的 α-氨基腈得到酰胺来证明。这项工作的重要特征包括广泛的官能团相容性、41% 至 89% 的产品产率、2° 和 3° 酰胺的克级合成、广泛的底物范围和 umpolung 策略。