N-(4-氰基苯基)-2-甲基丙酰胺 | 113715-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-氰基苯基)-2-甲基丙酰胺
• 英文名称: p-cyanoisobutyranilide
• 英文别名: 4'-cyano-2-methylpropananilide；N-(4-cyanophenyl)-2-methylpropanamide
• CAS: 113715-23-4
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD09040418
• 分子量: 188.229
• InChiKey: WQZFOMXBTXLFNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-氰基苯基)-2-甲基丙酰胺 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-2-methyl-N-(p-cyanophenyl)propanamide
  参考文献：
  名称：

  Electrochemical determination of the pKa of weak acids in N,N-dimethylformamide

  摘要：

  The electroreduction of NH-protic alpha-bromo amides in DMF generates an enolate-type base which undergoes a fast proton transfer from the parent compound (self-protonation), affording the corresponding reduced amide together with the conjugate base of the bromo amide. When an acid weaker than the bromo amide is added to the solution, a current increase in a potential region more negative than the main voltammetric reduction peak is observed under suitable conditions. The voltammetric pattern is in agreement with an unfavored protonation of the conjugate base of the starting compound by the added proton donor with regeneration of the electroactive bromo amide. The theoretical analysis of this reduction sequence has been carried out, and the voltammetric profiles have been simulated. Comparison of the experimental and simulated voltammetries led to the determination of the acidity difference, DELTA-pK(a), between the a-bromo amide and the added acid. For each alpha-bromo amide it was possible to obtain DELTA-pK(a) data ranging from 1.4 to 4.2. The use of a-bromo amides of different acidity with the same exogenous acids provided the link between the different sets of relative acidities. In this way, using six alpha-bromo amides, a relative acidity scale encompassing an overall pK(a) variation in DMF of about 10 units could be established. The relative scale was then anchored to the low pK(a) scale in DMF through both the determination of the acidity of selected acids and using a correlation between literature pK(a) data obtained in both DMF and DMSO. The application of this original electrochemical mechanism provided absolute pK(a) data in DMF ranging from about 16 to 26, i.e., a pK(a) region that is practically unexplored in this solvent.

  DOI：

  10.1021/ja00024a041
• 作为产物：
  描述：

  2-bromo-2-methyl-N-(p-cyanophenyl)propanamide 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-氰基苯基)-2-甲基丙酰胺
  参考文献：
  名称：

  Electrochemical determination of the pKa of weak acids in N,N-dimethylformamide

  摘要：

  The electroreduction of NH-protic alpha-bromo amides in DMF generates an enolate-type base which undergoes a fast proton transfer from the parent compound (self-protonation), affording the corresponding reduced amide together with the conjugate base of the bromo amide. When an acid weaker than the bromo amide is added to the solution, a current increase in a potential region more negative than the main voltammetric reduction peak is observed under suitable conditions. The voltammetric pattern is in agreement with an unfavored protonation of the conjugate base of the starting compound by the added proton donor with regeneration of the electroactive bromo amide. The theoretical analysis of this reduction sequence has been carried out, and the voltammetric profiles have been simulated. Comparison of the experimental and simulated voltammetries led to the determination of the acidity difference, DELTA-pK(a), between the a-bromo amide and the added acid. For each alpha-bromo amide it was possible to obtain DELTA-pK(a) data ranging from 1.4 to 4.2. The use of a-bromo amides of different acidity with the same exogenous acids provided the link between the different sets of relative acidities. In this way, using six alpha-bromo amides, a relative acidity scale encompassing an overall pK(a) variation in DMF of about 10 units could be established. The relative scale was then anchored to the low pK(a) scale in DMF through both the determination of the acidity of selected acids and using a correlation between literature pK(a) data obtained in both DMF and DMSO. The application of this original electrochemical mechanism provided absolute pK(a) data in DMF ranging from about 16 to 26, i.e., a pK(a) region that is practically unexplored in this solvent.

  DOI：

  10.1021/ja00024a041

文献信息

• IDO INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160289171A1

  公开（公告）日：2016-10-06

  There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.

  已披露的化合物可调节或抑制吲哌酮胺2,3-二氧化酶（IDO）的酶活性，含有该化合物的药物组合物以及利用本发明的化合物治疗增殖性疾病，如癌症、病毒感染和/或炎症性疾病的方法。
• HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS
  申请人：GiraFpharma LLC

  公开号：US20190023666A1

  公开（公告）日：2019-01-24

  Aminopyrazine compounds as modulators of an adenosine receptor are provided. The compounds may find use as therapeutic agents for the treatment of diseases mediated through a G-protein-coupled receptor signaling pathway and may find particular use in oncology.

  提供了氨基吡嗪化合物作为腺苷受体的调节剂。这些化合物可能作为治疗经由G蛋白偶联受体信号通路介导的疾病的治疗剂，并且可能在肿瘤学中发挥特定作用。
• Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as janus kinase inhibitors
  申请人：Rodgers D. James

  公开号：US20070135461A1

  公开（公告）日：2007-06-14

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，可以调节雅努斯激酶的活性，并且在治疗与雅努斯激酶活性相关的疾病中具有用处，例如免疫相关疾病、皮肤疾病、髓增生性疾病、癌症和其他疾病。
• HETEROARYL SUBSTITUTED PYRROLO[2,3-b]PYRIDINES AND PYRROLO[2,3-b]PYRIMIDINES AS JANUS KINASE INHIBITORS
  申请人：Rodgers James D.

  公开号：US20090181959A1

  公开（公告）日：2009-07-16

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，可调节Janus激酶的活性，并可用于治疗与Janus激酶活性相关的疾病，包括免疫相关疾病、皮肤疾病、髓系增生性疾病、癌症和其他疾病。
• Heteroaryl Substituted Pyrrolo[2,3-B] Pyridines And Pyrrolo[2,3-B] Pyrimidines As Janus Kinase Inhibitors
  申请人：Incyte Corporation

  公开号：US20140243360A1

  公开（公告）日：2014-08-28

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯[2,3-b]吡啶和杂环取代的吡咯[2,3-b]嘧啶，这些化合物可以调节Janus激酶的活性，适用于治疗与Janus激酶活性相关的疾病，例如免疫相关疾病、皮肤疾病、髓系增生性疾病、癌症和其他疾病。