N-(4-氨基苯基)-n-甲基苯甲酰胺 | 63721-85-7

• 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-氨基苯基)-n-甲基苯甲酰胺
• 英文名称: benzoic acid-(4-amino-N-methyl-anilide)
• 英文别名: Benzoesaeure-(4-amino-N-methyl-anilid)；N-Methyl-N-benzoyl-p-phenylendiamin；4-benzoyl(methyl)aminoaniline；N-(4-aminophenyl)-N-methylbenzamide
• CAS: 63721-85-7
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: QFFKTPBFSICAJY-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  422.4±37.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-氨基苯基)-n-甲基苯甲酰胺 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Morgan; Alcock, Journal of the Chemical Society, 1909, vol. 95, p. 1326,1328

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 N-(4-氨基苯基)-n-甲基苯甲酰胺
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Novel Series of Human Sirtuin-2-Selective Inhibitors

  摘要：

  Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2-anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of alpha-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.

  DOI：

  10.1021/jm3002108

文献信息

• [EN] PROTEIN KINASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE KINASE ET LEUR UTILISATION
  申请人：MERCK SERONO SA

  公开号：WO2009108670A1

  公开（公告）日：2009-09-03

  Disclosed are benzonaphthyridinyl derivative compounds and analogs thereof, pharmaceutical compositions comprising such compounds and processes for preparing the same. The compounds are useful in the treatment of diseases amenable to kinase signal transduction inhibition, regulation or modulation.

  揭示了苯并萘啶衍生物化合物及其类似物，包括含有这些化合物的药物组合物以及制备这些化合物的方法。这些化合物在治疗对激酶信号传导抑制、调节或调控敏感的疾病中很有用。
• Design, synthesis and preliminary pharmacological evaluation of new analogues of DM232 (unifiram) and DM235 (sunifiram) as cognition modulators
  作者：Elisabetta Martini、Monica Norcini、Carla Ghelardini、Dina Manetti、Silvia Dei、Luca Guandalini、Michele Melchiorre、Simona Pagella、Serena Scapecchi、Elisabetta Teodori、Maria Novella Romanelli

  DOI：10.1016/j.bmc.2008.10.017

  日期：2008.12

  A series of amides, structurally related to DM232 (unifiram) and DM235 (sunifiram), characterized by a 1,2,3,4-tetrahydropyrazino[2,1-a]isoindol-6(2H)-one, 1,4-diamino-cyclohexane or 1,4-diaminobenzene ring, have been synthesized and tested for cognition-enhancing activity in the mouse passive-avoidance test. Some of the compounds display good antiamnesic and procognitive activity, with higher potency

  在结构上与DM232（unifiram）和DM235（sunifiram）有关的一系列酰胺，其特征在于1,2,3,4-四氢吡嗪并[2,1-a] isoindol-6（2H）-one，1,4-已经合成了二氨基环己烷或1,4-二氨基苯环，并在小鼠被动回避测试中测试了其增强认知的能力。一些化合物显示出良好的抗记忆和认知活性，并且比吡乙酰胺具有更高的效能，而某些环己烷衍生物具有诱发失忆的特性。
• PROTEIN KINASE INHIBITORS AND USE THEREOF
  申请人：Huck Bayard R.

  公开号：US20110053906A1

  公开（公告）日：2011-03-03

  Disclosed are benzonaphthyridinyl derivative compounds and analogs thereof, pharmaceutical compositions comprising such compounds and processes for preparing the same. The compounds are useful in the treatment of diseases amenable to kinase signal transduction inhibition, regulation or modulation.

  本发明揭示了苯并萘啉衍生物化合物及其类似物，包括含有这些化合物的制药组合物和制备这些化合物的过程。这些化合物可用于治疗易于激酶信号传导抑制、调节或调控的疾病。
• US8735584B2
  申请人：——

  公开号：US8735584B2

  公开（公告）日：2014-05-27
• Design, Synthesis, and Biological Activity of a Novel Series of Human Sirtuin-2-Selective Inhibitors
  作者：Takayoshi Suzuki、Mohammed Naseer Ahmed Khan、Hideyuki Sawada、Erika Imai、Yukihiro Itoh、Katsura Yamatsuta、Natsuko Tokuda、Jun Takeuchi、Takuya Seko、Hidehiko Nakagawa、Naoki Miyata

  DOI：10.1021/jm3002108

  日期：2012.6.28

  Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2-anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of alpha-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.