3'-phenethyloxy-2-aniline-benzamide | 1382354-18-8

• 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: 3'-phenethyloxy-2-aniline-benzamide
• 英文别名: 2-((3-phenethoxyphenyl)amino)benzamide；2-[3-(2-phenylethoxy)anilino]benzamide
• CAS: 1382354-18-8
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: VVRUXFPJOVUDCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Iodo-3-(2-phenylethoxy)benzene 、 2-氨基苯甲酰胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 叔丁醇 为溶剂， 以6%的产率得到3'-phenethyloxy-2-aniline-benzamide
  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

• METHODS RELATED TO BRONCHIAL PREMALIGNANT LESION SEVERITY AND PROGRESSION
  申请人：Trustees of Boston University

  公开号：EP3840634A1

  公开（公告）日：2021-06-30
• [EN] COMPOUNDS AS SIRT2 INHIBITORS<br/>[FR] COMPOSÉS EN TANT QU'INHIBITEURS DE SIRT2
  申请人：IMP INNOVATIONS LTD

  公开号：WO2016067012A1

  公开（公告）日：2016-05-06

  The invention provides compounds of formula (I) or a salt thereof, wherein R1, R2, R3, R4, R5 and R6 are as defined in the specification. The invention also provides compositions comprising the compounds, and methods of using the compounds for the treatment of a disease in which inhibition of SIRT2 provides a therapeutic or prophylactic effect, for example cancers,metabolic disorders, inflammatory disorders,neurodegenerative disorders and central nervous system disorders.
• [EN] METHODS RELATED TO BRONCHIAL PREMALIGNANT LESION SEVERITY AND PROGRESSION<br/>[FR] MÉTHODES LIÉES À LA GRAVITÉ ET À LA PROGRESSION D'UNE LÉSION PRÉMALIGNE BRONCHIQUE
  申请人：UNIV BOSTON

  公开号：WO2020041243A1

  公开（公告）日：2020-02-27

  The technology described herein is directed to methods of treating and diagnosing bronchial premalignant lesions, e.g. by determining the lesion subtype using one or more biomarkers described herein.
• 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.