1-Iodo-3-(2-phenylethoxy)benzene | 1382354-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Iodo-3-(2-phenylethoxy)benzene
• CAS: 1382354-45-1
• 化学式: C₁₄H₁₃IO
• 分子量: 324.161
• InChiKey: GWXRUTGERVYBRW-UHFFFAOYSA-N

物化性质

• 沸点：
  395.6±25.0 °C(Predicted)
• 密度：
  1.523±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-碘苯酚 、 乙基溴苯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 1-Iodo-3-(2-phenylethoxy)benzene
  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] PYRIMIDINE AND NITROGEN-CONTAINING SIX-MEMBERED AROMATIC HETEROCYCLIC COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE AROMATIQUE À SIX CHAÎNONS CONTENANT DE LA PYRIMIDINE ET DE L'AZOTE ET SON UTILISATION<br/>[ZH] 嘧啶并含氮六元芳香杂环类化合物及其用途
  申请人：CSPC ZHONGQI PHARMACEUTICAL TECH SHIJIAZHUANG CO LTD

  公开号：WO2022268180A1

  公开（公告）日：2022-12-29

  提供一类式(I)所示的化合物或其前药、互变异构体、立体异构体、溶剂化物、同位素衍生物或药学上可接受的盐，所述化合物具有较强的MAT2A抑制作用，能够用于治疗和/或预防MAT2A介导的疾病、病症和病况，例如肿瘤等。